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Insights of Indole: A Novel Target in Medicinal Chemistry (A Review)

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Abstract

Cancer accounts for ten million dies in each year. There are ample number of Food and Drug Administration (FDA) approved drugs for this disease. Due to severe side effects and multiple drug resistance, the current drug therapies become ineffective. So, the newer chemical moieties/entities with less toxic are necessary for the development. The nitrogen bearing heterocycle indole scaffold is considered one of the most privileged pharmacophores in heterocyclic compounds. New indole-based drug may serve as an effective for the development of new drug against this disease. This review amalgamates the current advances on indole based molecular frameworks and their unique anticancer relevance as reported over the last two decades. It highlights an inclination in the use of indole-based drug crafting and subsequent emergence of several potent drug against a range of cancer diseases in the clinical and pre-clinical stages of development.

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REFERENCES

  1. Ferlay, J., Colombet, M., Soerjomataram, I., Parkin, D.M., Pineros, M., Znaor, A., and Bray, F., Int. J. Cancer, 2021, vol. 149, no. 4, p. 778. https://doi.org/10.1002/ijc.31937

    Article  CAS  Google Scholar 

  2. Jordan, M.A. and Wilson, L., Nat. Rev. Cancer, 2004, vol. 4, no. 4, p. 253. https://doi.org/10.1038/nrc1317

    Article  CAS  PubMed  Google Scholar 

  3. Dumontet, C. and Jordan, M.A., Nat. Rev. Drug Discov., 2010, vol. 9, no. 10, p. 790. https://doi.org/10.1038/nrd3253

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Patil, S.A., Patil, R., and Miller, D.D., Curr. Med. Chem., 2009, vol. 16, no. 20, p. 2531. https://doi.org/10.2174/092986711794480195

    Article  CAS  PubMed  Google Scholar 

  5. Patil, S.A., Patil, R., and Miller, D.D., Curr. Org. Chem., 2008, vol. 12, no. 9, p. 691. https://doi.org/10.2174/138527208784567223

    Article  CAS  Google Scholar 

  6. Lakhdar, S., Westermaier, M., Terrier, F., Goumont, R., Boubaker, T., Ofial, A.R., and Mayr, H., J. Org. Chem., 2006, vol. 71, no. 24, p. 9088. https://doi.org/10.1021/jo0614339

    Article  CAS  PubMed  Google Scholar 

  7. Diss, L.B., Robinson, S.D., Wu, Y., Fidalgo, S., Yeoman, M.S., and Patel, B.A., ACS Chem. Neurosci., 2013, vol. 4, no. 5, p. 879. https://doi.org/10.1021/cn4000617

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. de Sa Alves, F.R., Barreiro, E.J., and Manssour Fraga, C.A., Mini Rev. Med. Chem., 2009, vol. 9, no. 7, p. 782. https://doi.org/10.2174/138955709788452649

    Article  PubMed  Google Scholar 

  9. Sivaprasad, G., Perumal, P.T., Prabavathy, V.R., and Mathivanan, N., Bioorg. Med. Chem. Lett., 2006, vol. 16, no. 24, p. 6302. https://doi.org/10.1016/j.bmcl.2006.09.019

    Article  CAS  PubMed  Google Scholar 

  10. Donawade, D.S., Raghu, A.V., and Gadaginamath, G.S., Indian J. Chem. (B), 2006, vol. 45, p. 689.

    Google Scholar 

  11. Samosorn, S., Bremner, J.B., Ball, A., and Lewis, K., Bioorg. Med. Chem., 2006, vol. 14, no. 3, p. 857–865. https://doi.org/10.1016/j.bmc.2005.09.019

    Article  CAS  PubMed  Google Scholar 

  12. Al-Hiari, Y.M., Qaisi, A.M., El-Abadelah, M.M., and Voelter, W., Monat. Chem., 2006, vol. 137, p. 243. https://doi.org/10.1007/s00706-005-0424-6

    Article  CAS  Google Scholar 

  13. Leboho, T.C., Michael, J.P., van Otterlo, W.A.L., van Vuuren, S.F., and de Koning, C.B., Bioorg. Med. Chem. Lett., 2009, vol. 19, no. 17, p. 4948. https://doi.org/10.1016/j.bmcl.2009.07.091

  14. Hu, W., Guo, Z., Yi, X., Guo, C., Chu, F., and Cheng, G., Bioorg. Med. Chem., 2003, vol. 11, no. 24, p. 5539. https://doi.org/10.1016/j.bmc.2003.09.008

    Article  CAS  PubMed  Google Scholar 

  15. Narayana, B., Ashalatha, B.V., Raj, K.K.V., Fernandes, J., and Sarojini, B.K., Bioorg. Med. Chem., 2005, vol. 13, no. 15, p. 4638. https://doi.org/10.1016/j.bmc.2005.04.068

    Article  CAS  PubMed  Google Scholar 

  16. Radwan, M.A.A., Ragab, E.A., Sabry, N.M., and El-Shenawy, S.M., Bioorg. Med. Chem., 2007, vol. 15, no. 11, p. 3832. https://doi.org/10.1016/j.bmc.2007.03.024

    Article  CAS  PubMed  Google Scholar 

  17. Kuduk, S.D., Chang, R.K., Wai, J.M.-C., Di Marco, C.N., Cofre, V., DiPardo, R.M., Cook, S.P., Cato, M.J., Jovanovska, A., and Urban, M.O., Bioorg. Med. Chem. Lett., 2009, vol. 19, no. 15, p. 4059. https://doi.org/10.1016/j.bmcl.2009.06.021

    Article  CAS  PubMed  Google Scholar 

  18. Dharmendra, K., Narendra, K., and Taruna, S., Int. J. Eng. Sci. Tech., 2010, vol. 2, no. 7, p. 2553.

    Google Scholar 

  19. Rahaman, S.A., Prasad, Y.R., Bhuvaneswari, K., and Kumar, P., Int. J. Chem. Tech. Res., 2010, vol. 2, p. 16.

    CAS  Google Scholar 

  20. Battaglia, S., Boldrini, E., Da Settimo, F., Dondio, G., La Motta, C., Marini, A.M., and Primofiore, G., Eur. J. Med. Chem., 1999, vol. 34, no. 2, p. 93. https://doi.org/10.1016/S0223-5234(99)80044-0

    Article  CAS  Google Scholar 

  21. Kaushik, N.K., Kaushik, N., Attri, P., Kumar, N., Kim, C.H., Verma, A.K., and Choi, E.H., Molecules, 2013, vol. 18, p. 6620. https://doi.org/10.3390/molecules18066620

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. Estevao, M.S., Carvalho, L.C., Ribeiro, D., Couto, D., Freitas, M., Gomes, A., Ferreira, L.M., Fernandes, E., and Marques, M.M.B., Eur. J. Med. Chem., 2010, vol. 45, no. 11, p. 4869. https://doi.org/10.1016/j.ejmech.2010.07.059

    Article  CAS  PubMed  Google Scholar 

  23. Mohamed, M.S., Youns, M.M., and Ahmed, N.M., Med. Chem. Res., 2014, vol. 23, p. 3374. https://doi.org/10.1007/s00044-014-0916-1

  24. Karaaslan, C., Kadri, H., Coban, T., Suzen, S., and Westwell, A.D., Bioorg. Med. Chem. Lett., 2013, vol. 23, no. 9, p. 2671. https://doi.org/10.1016/j.bmcl.2013.02.090

    Article  CAS  PubMed  Google Scholar 

  25. Li, Y.-Y., Wu, H.-S., Tang, L., Feng, C.-R., Yu, J.-H., Li, Y., Yang, Y.-S., Yang, B., and He, Q.-J., Pharmacol. Res., 2007, vol. 56, no. 4, p. 335. https://doi.org/10.1016/j.phrs.2007.08.002

  26. Abdel-Gawad, H., Mohamed, H.A., Dawood, K.M., and Badria, F.A.-R., Chem. Pharm. Bull., 2010, vol. 58, no. 11, p. 1529. https://doi.org/10.1248/cpb.58.1529

    Article  CAS  Google Scholar 

  27. Ghanei-Nasab, S., Khoobi, M., Hadizadeh, F., Marjani, A., Moradi, A., Nadri, H., Emami, S., Foroumadi, A., and Shafiee, A., Eur. J. Med. Chem., 2016, vol. 121, p. 40. https://doi.org/10.1016/j.ejmech.2016.05.014

    Article  CAS  PubMed  Google Scholar 

  28. Akrami, H., Mirjalili, B.F., Khoobi, M., Nadri, H., Moradi, A., Sakhteman, A., Emami, S., Foroumadi, A., and Shafiee, A., Eur. J. Med. Chem., 2014, vol. 84, p. 375. https://doi.org/10.1016/j.ejmech.2014.01.017

  29. MacDonough, M.T., Strecker, T.E., Hamel, E., Hall, J.J., Chaplin, D.J., Trawick, M.L., and Pinney, K.G., Bioorg. Med. Chem., 2013, vol. 21, no. 21, p. 6831. https://doi.org/10.1016/j.bmc.2013.07.028

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. Akkoc, M.K., Yuksel, M.Y., Durmaz, I., and Atalay, R.C., Turkish. J. Chem., 2012, vol. 36, no. 4, p. 515.

    Google Scholar 

  31. Kumar, D., Kumar, N.M., Noel, B., and Shah, K., Eur. J. Med. Chem., 2012, vol. 55, p. 432. https://doi.org/10.1016/j.ejmech.2012.06.047

    Article  CAS  PubMed  Google Scholar 

  32. Queiroz, M.-J.R.P., Abreu, A.S., Carvalho, M.S.D., Ferreira, P.M.T., Nazareth, N., and Nascimento, M.S.-J., Bioorg. Med. Chem., 2008, vol. 16, no. 10, p. 5584. https://doi.org/10.1016/j.bmc.2008.04.004

    Article  CAS  PubMed  Google Scholar 

  33. Zhang, F., Zhao, Y., Sun, L., Ding, L., Gu, Y., and Gong, P., Eur. J. Med. Chem., 2011, vol. 46, no. 7, p. 3149. https://doi.org/10.1016/j.ejmech.2011.03.055

    Article  CAS  PubMed  Google Scholar 

  34. Ahmad, A., Sakr, W., and Wahidur Rahman, K.M., Curr. Drug Targets., 2010, vol. 11, no. 6, p. 652. https://doi.org/10.2174/138945010791170923

    Article  CAS  PubMed  Google Scholar 

  35. Almagro, L., Fernandez-Perez, F., and Pedreno, M.A., Molecules, 2015, vol. 20, no. 2, p. 2973. https://doi.org/10.3390/molecules20022973

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  36. Bradner, W.T., Cancer Treat. Rev., 2001, vol. 27, no. 1, p. 35. https://doi.org/10.1053/ctrv.2000.0202

    Article  CAS  PubMed  Google Scholar 

  37. Kumar, D. and Rawat, D.S., Oppor. Chall. Scope Nat. Prod. Med. Chem., 2011, vol. 213, p. 268.

    Google Scholar 

  38. Lake, R.J., Blunt, J.W., and Munro, M.H.G., Aust. J. Chem., 1989, vol. 42, no. 7, p. 1201. https://doi.org/10.1071/CH9891201

    Article  CAS  Google Scholar 

  39. Hu, M.J., Zhang, B., Yang, H., Liu, Y., Chen, Y., Ma, T., Lu, L., You, W., and Zhao, P., Chem. Biol. Drug Des., 2015, vol. 86, no. 6, p. 1491. https://doi.org/10.1111/cbdd.12616

    Article  CAS  PubMed  Google Scholar 

  40. Diao, P.-C., Li, Q., Hu, M.-J., Ma, Y.-F., You, W.-W., Hong, K.H., and Zhao, P.-L., Eur. J. Med. Chem., 2017, vol. 134, p. 110. https://doi.org/10.1016/j.ejmech.2017.04.011

    Article  CAS  PubMed  Google Scholar 

  41. Kamath, P.R., Sunil, D., Ajees, A.A., Pai, K.S.R., and Das, S., Bioorg. Chem., 2015, vol. 63, p. 101. https://doi.org/10.1016/j.bioorg.2015.10.001

    Article  CAS  PubMed  Google Scholar 

  42. Shankaraiah, N., Siraj, K.P., Nekkanti, S., Srinivasulu, V., Sharma, P., Senwar, K.R., Sathish, M., Vishnuvardhan, M., Ramakrishna, S., and Jadala, C., Bioorg. Chem., 2015, vol. 59, p. 130. https://doi.org/10.1016/j.bioorg.2015.02.007

    Article  CAS  PubMed  Google Scholar 

  43. Rambabu, D., Raja, G., Sreenivas, B.Y., Seerapu, G.P.K., Kumar, K.L., Deora, G.S., Haldar, D., Rao, M.V.B., and Pal, M., Bioorg. Med. Chem. Lett., 2013, vol. 23, no. 5, p. 1351. https://doi.org/10.1016/j.bmcl.2012.12.089

    Article  CAS  PubMed  Google Scholar 

  44. Yan, J., Chen, J., Zhang, S., Hu, J., Huang, L., and Li, X., J. Med. Chem., 2016, vol. 59, no. 11, p. 5264. https://doi.org/10.1021/acs.jmedchem.6b00021

    Article  CAS  PubMed  Google Scholar 

  45. Panathur, N., Gokhale, N., Dalimba, U., Koushik, P.V., Yogeeswari, P., and Sriram, D., Med. Chem. Res., 2016, vol. 25, p. 135. https://doi.org/10.1016/j.bmcl.2015.05.015

    Article  CAS  Google Scholar 

  46. Ji, X.Y, Xue, S.T., Zhan, Y.C., Shen, J.J., Wu, L.T., Jin, J., Wang, Z., and Li, Z.R., Eur. J. Med. Chem., 2014, vol. 83, p. 409. https://doi.org/10.1016/j.ejmech.2014.05.043

    Article  CAS  PubMed  Google Scholar 

  47. Lafayette, E.A., de Almeida, S.M.V., Santos, R.V.C., de Oliveira, J.F., da Cruz Amorim, C.A., da Silva, R.M.F., da Rocha Pitta, M.G., da Rocha Pitta, I., de Moura, R.O., and de Carvalho Junior, L.B., Eur. J. Med. Chem., 2017, vol. 136, p. 511. https://doi.org/10.1016/j.ejmech.2017.05.012

    Article  CAS  PubMed  Google Scholar 

  48. Kamath, P.R., Sunil, D., Joseph, M.M., Salam, A.A.A., and Sreelekha, T.T., Eur. J. Med. Chem., 2017, vol. 136, p. 442. https://doi.org/10.1016/j.ejmech.2017.05.032

    Article  CAS  PubMed  Google Scholar 

  49. Nagesh, N., Raju, G., Srinivas, R., Ramesh, P., Reddy, M.D., and Reddy, C.R., Biochim. Biophys. Acta., 2015, vol. 1850, no. 1, p. 129. https://doi.org/10.1016/j.bbagen.2014.10.004

    Article  CAS  PubMed  Google Scholar 

  50. Cai, M., Hu, J., Tian, J.-L., Yan, H., Zheng, C.-G., and Hu, W.-L., Chinese Chem. Lett., 2015, vol. 26, no. 6, p. 675. https://doi.org/10.1016/j.cclet.2015.03.015

    Article  CAS  Google Scholar 

  51. Patel, T., Gaikwad, R., Jain, K., Ganesh, R., Bobde, Y., Ghosh, B., Das, K., and Gayen, S., ChemistrySelect, 2019, vol. 4, no. 15, p. 4478. https://doi.org/10.1002/slct.201900088

    Article  CAS  Google Scholar 

  52. Mphahlele, M.J., Mmonwa, M.M., Aro, A., McGaw, L.J., and Choong, Y.S., Int. J. Mol. Sci., 2018, vol. 19, no. 8, p. 2232. https://doi.org/10.3390/ijms19082232

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  53. Peerzada, M.N., Khan, P., Ahmad, K., Hassan, M.I., and Azam, A., Eur. J. Med. Chem., 2018, vol. 155, p. 13. https://doi.org/10.1016/j.ejmech.2018.05.034

    Article  CAS  PubMed  Google Scholar 

  54. La Regina, G., Bai, R., Coluccia, A., Famiglini, V., Pelliccia, S., Passacantilli, S., Mazzoccoli, C., Ruggieri, V., Verrico, A., Miele, A., Monti, L., Nalli, M., Alfonsi, R., Di Marcotullio, L., Gulino, A., Ricci, B., Soriani, A., Santoni, A., Caraglia, M., Porto, S., Da Pozzo, E., Martini, C., Brancale, A., Marinelli, L., Novellino, E., Vultaggio, S., Varasi, M., Mercurio, C., Bigogno, C., Dondio, G., Hamel, E., Lavia, P., and Silvestri, R., J. Med. Chem., 2015, vol. 58, no. 15, p. 5789. https://doi.org/10.1021/acs.jmedchem.5b00310

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  55. Aneja, B., Arif, R., Perwez, A., Napoleon, J.V, Hasan, P., Rizvi, M.M.A., Azam, A., and Abid, M., ChemistrySelect, 2018, vol. 3, no. 9, p. 2638. https://doi.org/10.1002/slct.201702913

    Article  CAS  Google Scholar 

  56. Zhang, Q., Lv, J., He, F., Yu, C., Qu, Y., Zhang, X., Xu, A., and Wu, J., Bioorg. Med. Chem., 2019, vol. 27, no. 8, p. 1595. https://doi.org/10.1016/j.bmc.2019.03.008

    Article  CAS  PubMed  Google Scholar 

  57. Dolusic, E., Larrieu, P., Moineaux, L., Stroobant, V., Pilotte, L., Colau, D., Pochet, L., Van den Eynde, B., Masereel, B., Wouters, J., and Frederick, R., J. Med. Chem., 2011, vol. 54, no. 15, p. 5320. https://doi.org/10.1021/jm2006782

    Article  CAS  PubMed  Google Scholar 

  58. Anouar, E.H., Moustapha, M.E., Taha, M., Geesi, M.H., Farag, Z.R., Rahim, F., Almandil, N.B., Farooq, R.K., Nawaz, M., and Mosaddik, A., Molecules, 2019, vol. 24, no. 5, p. 963. https://doi.org/10.3390/molecules24050963

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  59. Zhuang, S.-H., Lin, Y.-C., Chou, L.-C., Hsu, M.-H., Lin, H.-Y., Huang, C.-H., Lien, J.-C., Kuo, S.-C., and Huang, L.-J., Eur. J. Med. Chem., 2013, vol. 66, p. 466. https://doi.org/10.1016/j.ejmech.2013.06.012

    Article  CAS  PubMed  Google Scholar 

  60. Gurkan-Alp, A.S., Mumcuoglu, M., Andac, C.A., Dayanc, E., Cetin-Atalay, R., and Buyukbingol, E., Eur. J. Med. Chem., 2012, vol. 58, p. 346. https://doi.org/10.1016/j.ejmech.2012.10.013

    Article  CAS  PubMed  Google Scholar 

  61. Ma, J., Bao, G., Wang, L., Li, W., Xu, B., Du, B., Lv, J., Zhai, X., and Gong, P., Eur. J. Med. Chem., 2015, vol. 96, p. 173. https://doi.org/10.1016/j.ejmech.2015.04.018

    Article  CAS  PubMed  Google Scholar 

  62. Kumar, T.O.S., Mahadevan, K.M., and Kumara, M.N., Int. J. Pharm. Pharm. Sci., 2014, vol. 6, no. 2, p. 137.

    Google Scholar 

  63. Kumar, D., Kumar, N.M., Chang, K.-H., Gupta, R., and Shah, K., Eur. Med. Chem., 2010, vol. 45, no. 10, p. 4664. https://doi.org/10.1016/j.ejmech.2010.07.023

    Article  CAS  Google Scholar 

  64. Liao, S.-R., Qin, X.-C., Wang, Z., Li, D., Xu, L., Li, J.-S., Tu, Z.-C., and Liu, Y., Eur. J. Med. Chem., 2016, vol. 121, p. 500. https://doi.org/10.1016/j.ejmech.2016.06.002

    Article  CAS  PubMed  Google Scholar 

  65. Han, K., Wang, H., Song, B., Li, Y., Ding, W.N., Zhao, H., Sun, H., Teng, Y., and Yu, P., J. Chem. Pharm. Res., 2014, vol. 6, no. 9, p. 376.

    Google Scholar 

  66. Yousif, M.N.M., Hussein, H.A.R., Yousif, N.M., El-Manawaty, M.A., and El-Sayed, W.A., J. Appl. Pharm. Sci., 2019, vol. 9, no. 1, p. 6. https://doi.org/10.7324/JAPS.2019.90102

    Article  CAS  Google Scholar 

  67. Choppara, P., Prasad, Y.V., Rao, C.V., Krishna, K.H., Trimoorthulu, G., Rao, G.U.M., Rao, J.V., Bethu, M.S., and Murthy, Y.L.N., Arab. J. Chem., 2019, vol. 12, no. 8, p. 2328. https://doi.org/10.1016/j.arabjc.2015.02.006

    Article  CAS  Google Scholar 

  68. Kaur, H., Singh, J., and Narasimhan, B., BMC Chem., 2019, vol. 13, p. 1. https://doi.org/10.1186/s13065-019-0558-y

    Article  CAS  Google Scholar 

  69. Mishra, D.P., Khan, M.A., Yadav, D.K., Rawat, A.K., Singh, R.K., Ahamad, T., Hussain, M.K., Saquib, M., and Khan, M.F., ChemistrySelect, 2018, vol. 3, no. 29, p. 8468. https://doi.org/10.1002/slct.201801475

    Article  CAS  Google Scholar 

  70. Nesi, G., Sestito, S., Mey, V., Ricciardi, S., Falasca, M., Danesi, R., Lapucci, A., Breschi, M.C., Fogli, S., and Rapposelli, S., ACS Med. Chem. Lett., 2013, vol. 4, no. 12, p. 1137. https://doi.org/10.1021/ml400162g

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  71. Zhao, B., Xiao, Z., Qi, J., Luo, R., Lan, Z., Zhang, Y., Hu, X., Tang, Q., Zheng, P., and Xu, S., Eur. J. Med. Chem., 2019, vol. 163, p. 367. https://doi.org/10.1016/j.ejmech.2018.11.069

    Article  CAS  PubMed  Google Scholar 

  72. Nakajima, E., Helfrich, B., Chan, D., Zhang, Z., Hirsch, F.R., Chen, V., Ma, D., and Bunn, Jr.P.A., J. Clin. Oncol., 2006, vol. 24, no. 18, p. 13138. https://doi.org/10.1200/jco.2006.24.18_suppl.13138

    Article  Google Scholar 

  73. Wang, M., Xu, L., Gao, M., Miller, K.D., Sledge, G.W., and Zheng, Q.-H., Bioorg. Med. Chem. Lett., 2011, vol. 21, no. 6, p. 1649. https://doi.org/10.1016/j.bmcl.2011.01.100

    Article  CAS  PubMed  Google Scholar 

  74. Crump, M., Leppa, S., Fayad, L., Lee, J.J., Di Rocco, A., Ogura, M., Hagberg, H., Schnell, F., Rifkin, R., Mackensen, A., Offner, F., Pinter-Brown, L., Smith, S., Tobinai, K., Yeh, S.P., Hsi, E.D., Nguyen, T., Shi, P., Hahka-Kemppinen, M., Thornton, D., Lin, B., Kahl, B., Schmitz, N., Savage, K.J., and Habermann, T., J. Clin. Oncol., 2016, vol. 34, no. 21, p. 2484. https://doi.org/10.1200/JCO.2015.65.7171

    Article  CAS  PubMed  Google Scholar 

  75. Remsing Rix, L.L., Kuenzi, B.M., Luo, Y., RemilyWood, E., Kinose, F., Wright, G., Li, J., Koomen, J.M., Haura, E.B., and Lawrence, H.R., ACS Chem. Biol., 2014, vol. 9, no. 2, p. 353. https://doi.org/10.1021/cb400660a

    Article  CAS  PubMed  Google Scholar 

  76. Scagliotti, G.V., Shuster, D., Orlov, S., von Pawel, J., Shepherd, F.A., Ross, J.S., Wang, Q., Schwartz, B., and Akerley, W., J. Thorac. Oncol., 2018, vol. 13, no. 6, p. 849. https://doi.org/10.1016/j.jtho.2017.12.009

    Article  CAS  PubMed  Google Scholar 

  77. Cong, H., Zhao, X., Castle, B.T., Pomeroy, E.J., Zhou, B., Lee, J., Wang, Y., Bian, T., Miao, Z., and Zhang, W., Mol. Pharm., 2018, vol. 15, no. 9, p. 3892. https://doi.org/10.1021/acs.molpharmaceut.8b00359

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  78. Das Mukherjee, D., Kumar, N.M., Tantak, M.P., Das, A., Ganguli, A., Datta, S., Kumar, D., and Chakrabarti, G., Biochemistry, 2016, vol. 55, no. 21, p. 3020. https://doi.org/10.1021/acs.biochem.5b01127

    Article  CAS  PubMed  Google Scholar 

  79. Chen, C.-W., Wu, M.-H., Chen, Y.-F., Yen, T.-Y., Lin, Y.-W., Chao, S.-H., Tala, S., Tsai, T.-H., Su, T.-L., and Lee, T.-C., Neoplasia, 2016, vol. 18, no. 4, p. 199. https://doi.org/10.1016/j.neo.2016.02.005

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  80. Chang, S.-M., Christian, W., Wu, M.-H., Chen, T.-L., Lin, Y.-W., Suen, C.-S., Pidugu, H.B., Detroja, D., Shah, A., and Hwang, M.-J., Eur. J. Med. Chem., 2017, vol. 127, p. 235. https://doi.org/10.1016/j.ejmech.2016.12.046

    Article  CAS  PubMed  Google Scholar 

  81. Song, Y.-L., Dong, Y.-F., Yang, T., Zhang, C.-C., Su, L.-M., Huang, X., Zhang, D.-N., Yang, G.-L., and Liu, Y.-X., Bioorg. Med. Chem., 2013, vol. 21, no. 24, p. 7624. https://doi.org/10.1016/j.bmc.2013.10.034

    Article  CAS  PubMed  Google Scholar 

  82. Nadkarni, D.H., Wang, F., Wang, W., Rayburn, E.R., Ezell, S.J., Murugesan, S., Velu, S.E., and Zhang, R., Med. Chem., 2009, vol. 5, no. 3, p. 227. https://doi.org/10.2174/157340609788185873

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  83. Zhao, X., Dong, W., Gao, Y., Shin, D.-S., Ye, Q., Su, L., Jiang, F., Zhao, B., and Miao, J., Sci. Rep., 2017, vol. 7, no. 1, p. 3919. https://doi.org/10.1038/s41598-017-04411-3

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  84. Hu, H., Wu, J., Ao, M., Wang, H., Zhou, T., Xue, Y., Qiu, Y., Fang, M., and Wu, Z., Chem. Biol. Drug Des., 2016, vol. 88, no. 5, p. 766. https://doi.org/10.1111/cbdd.12808

    Article  CAS  PubMed  Google Scholar 

  85. Huang, S., Hsu, P., Chen, M., Li, W., More, S.V., Lu, K., and Wang, Y., Int. J. Cancer, 2012, vol. 131, no. 3, p. 722. https://doi.org/10.1002/ijc.26401

    Article  CAS  PubMed  Google Scholar 

  86. Skouta, R., Hayano, M., Shimada, K., and Stockwell, B.R., Bioorg. Med. Chem. Lett., 2012, vol. 22, no. 17, p. 5707. https://doi.org/10.1016/j.bmcl.2012.06.077

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  87. Pingaew, R., Mandi, P., Prachayasittikul, V., Thongnum, A., Prachayasittikul, S., Ruchirawat, S., and Prachayasittikul, V., ACS Omega, 2021, vol. 6, no. 47, p. 31854. https://doi.org/10.1021/acsomega.1c04552

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  88. Chao, W.-R., Yean, D., Amin, K., Green, C., and Jong, L., J. Med. Chem., 2007, vol. 50, no. 15, p. 3412. https://doi.org/10.1021/jm070040e

    Article  CAS  PubMed  Google Scholar 

  89. Andreani, A., Burnelli, S., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Varoli, L., Landi, L., Prata, C., Berridge, M.V., Grasso, C., Fiebig, H.H., Kelter, G., Burger, A.M., and Kunkel, M.W., J. Med. Chem., 2008, vol. 51, no. 15, p. 4563. https://doi.org/10.1021/jm800194k

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  90. Sharma, V., Kalia, R., Raj, T., Gupta, V.K., Suri, N., Saxena, A.K., Sharma, D., Bhella, S.S., Singh, G., and Ishar, M.P.S., Acta Pharm. Sin. (B), 2012, vol. 2, no. 1, p. 32. https://doi.org/10.1016/j.apsb.2011.12.009

    Article  CAS  Google Scholar 

  91. Kamel, M.M., Abdel-Hameid, M.K., El-Nassan, H.B., and El-Khouly, E.A., Med. Chem., 2019, vol. 15, no. 8, p. 873. https://doi.org/10.2174/1573406415666190408125514

    Article  CAS  PubMed  Google Scholar 

  92. Cascioferro, S., Li Petri, G., Parrino, B., El Hassouni, B., Carbone, D., Arizza, V., Perricone, U., Padova, A., Funel, N., Peters, G.J., Cirrincione, G., Giovannetti, E., and Diana, P., Molecules, 2020, vol. 25, no. 2, p. 329. https://doi.org/10.3390/molecules25020329

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  93. Patravale, A.A., Gore, A.H., Kolekar, G.B., Deshmukh, M.B., Choudhari, P.B., Bhatia, M.S., Prabhu, S., Jamdhade, M.D., Patole, M.S., and Anbhule, P.V., J. Taiwan Inst. Chem. Eng., 2016, vol. 68, p. 105. https://doi.org/10.1016/j.jtice.2016.09.034

    Article  CAS  Google Scholar 

  94. Eldehna, W.M., El-Naggar, D.H., Hamed, A.R., Ibrahim, H.S., Ghabbour, H.A., and Abdel-Aziz, H.A., J. Enzyme Inhib. Med. Chem., 2018, vol. 33, no. 1, p. 309. https://doi.org/10.1080/14756366.2017.1417276

    Article  CAS  PubMed  Google Scholar 

  95. Lotfy, G., Said, M.M., El Sayed, H., El Sayed, H., Al-Dhfyan, A., Aziz, Y.M.A., and Barakat, A., Bioorg. Med. Chem., 2017, vol. 25, no. 4, p. 1514. https://doi.org/10.1016/j.bmc.2017.01.014

    Article  CAS  PubMed  Google Scholar 

  96. Vine, K.L., Locke, J.M., Ranson, M., Pyne, S.G., and Bremner, J.B., Bioorg. Med. Chem., 2007, vol. 15, no. 2, p. 931. https://doi.org/10.1016/j.bmc.2006.10.035

    Article  CAS  PubMed  Google Scholar 

  97. Kumar, S.B., Ravinder, M., Kishore, G., Jayathirtha Rao, V., Yogeeswari, P., and Sriram, D., Med. Chem. Res., 2014, vol. 23, p. 1934. https://doi.org/

    Article  CAS  PubMed  Google Scholar 

  98. Eldehna, W.M., Abo-Ashour, M.F., Nocentini, A., Gratteri, P., Eissa, I.H., Fares, M., Ismael, O.E., Ghabbour, H.A., Elaasser, M.M., Abdel-Aziz, H.A., and Supuran, C.T., Eur. J. Med. Chem., 2017, vol. 139, p. 250. https://doi.org/10.1016/j.ejmech.2017.07.073

    Article  CAS  PubMed  Google Scholar 

  99. Nagarsenkar, A., Guntuku, L., Guggilapu, S.D., Gannoju, S., Naidu, V.G.M., and Bathini, N.B., Eur. J. Med. Chem., 2016, vol. 124, p. 782. https://doi.org/10.1016/j.ejmech.2016.09.009

    Article  CAS  PubMed  Google Scholar 

  100. Zhang, L., Chen, F., Wang, J., Chen, Y., Zhang, Z., Lin, Y., and Zhu, X., RSC Adv., 2015, vol. 5, no. 118, p. 97816. https://doi.org/10.1039/C5RA21217K

    Article  CAS  Google Scholar 

  101. Han, C., Zhang, T., Zhang, A., Wang, D., Shi, W., and Tao, J., Synthesis, 2014, vol. 46, no. 10, p. 1389. https://doi.org/10.1055/s-0033-1341028

    Article  CAS  Google Scholar 

  102. Konyar, D., Andac, C.A., and Buyukbingol, E., Lett. Drug Des. Discov., 2018, vol. 15, no. 1, p. 37. https://doi.org/10.2174/1570180814666170810120634

    Article  CAS  Google Scholar 

  103. Islam, M.S., Ghawas, H.M., El-Senduny, F.F., AlMajid, A.M., Elshaier, Y.A.M.M., Badria, F.A., and Barakat, A., Bioorg. Chem., 2019, vol. 82, p. 423. https://doi.org/10.1016/j.bioorg.2018.10.036

    Article  CAS  PubMed  Google Scholar 

  104. Wu, L., Liu, Y., and Li, Y., Molecules, 2018, vol. 23, no. 9, p. 2330. https://doi.org/10.3390/molecules23092330

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  105. de Oliveira, J.F., Lima, T.S., Vendramini-Costa, D.B., de Lacerda Pedrosa, S.C.B., Lafayette, E.A., da Silva, R.M.F., de Almeida, S.M.V., de Moura, R.O., Ruiz, A.L.T.G., de Carvalho, J.E., and de Lima, M.D.C.A., Eur. J. Med. Chem., 2017, vol. 136, p. 305. https://doi.org/10.1016/j.ejmech.2017.05.023

    Article  CAS  PubMed  Google Scholar 

  106. Ibrahim, H.S., Abou-Seri, S.M., Ismail, N.S.M., Elaasser, M.M., Aly, M.H., and Abdel-Aziz, H.A., Eur. J. Med. Chem., 2016, vol. 108, p. 415. https://doi.org/10.1016/j.ejmech.2015.11.047

    Article  CAS  PubMed  Google Scholar 

  107. Nolan, V.C., Rafols, L., Harrison, J., SoldevilaBarreda, J.J., Crosatti, M., Garton, N.J., Wegrzyn, M., Timms, D.L., Seaton, C.C., Sendron, H., Azmanova, M., Barry, N.P.E., Pitto-Barry, A., and Cox, J.A.G., Curr. Res. Microb. Sci., 2022, vol. 3, p. 100099. https://doi.org/10.1016/j.crmicr.2021.100099

    Article  CAS  PubMed  Google Scholar 

  108. Haribabu, J., Jeyalakshmi, K., Arun, Y., Bhuvanesh, N.S.P., Perumal, P.T., and Karvembu, R., J. Biol. Inorg. Chem., 2017, vol. 22, p. 461. https://doi.org/10.1007/s00775-016-1424-1

    Article  CAS  PubMed  Google Scholar 

  109. Quirante, J., Dubar, F., Gonzalez, A., Lopez, C., Cascante, M., Cortes, R., Forfar, I., Pradines, B., and Biot, C., J. Organomet. Chem., 2011, vol. 696, no. 5, p. 1011. https://doi.org/10.1016/j.jorganchem.2010.11.021

    Article  CAS  Google Scholar 

  110. Soldevila-Barreda, J.J., Fawibe, K.B., Azmanova, M., Rafols, L., Pitto-Barry, A., Eke, U.B., and Barry, N.P.E., Molecules, 2020, vol. 25, no. 19, p. 4540. https://doi.org/10.3390/molecules25194540

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  111. Varma, R.R., Pandya, J.G., Vaidya, F.U., Pathak, C., Bhatt, B.S., and Patel, M.N., Chem. Biol. Interact., 2020, vol. 330, p. 109231. https://doi.org/10.1016/j.cbi.2020.109231

    Article  CAS  PubMed  Google Scholar 

  112. Tolan, D., Almotairy, A.R.Z., Howe, O., Devereux, M., Montagner, D., and Erxleben, A., Inorg. Chim. Acta, 2019, vol. 492, p. 262. https://doi.org/10.1016/j.ica.2019.04.038

    Article  CAS  Google Scholar 

  113. Hemmings, B.A., and Restuccia, D.F., Cold Spring Harb. Perspect. Biol., 2012, vol. 4, no. 9, p. a011189. https://doi.org/10.1101/cshperspect.a011189

  114. Altomare, D.A. and Testa, J.R., Oncogene, 2005, vol. 24, no. 50, p. 7455. https://doi.org/10.1038/sj.onc.1209085

    Article  CAS  PubMed  Google Scholar 

  115. Cheng, H., Shcherba, M., Pendurti, G., Liang, Y., Piperdi, B., and Perez-Soler, R., Lung Cancer Manag., 2014, vol. 3, no. 1, p. 67. https://doi.org/10.2217/lmt.13.72

    Article  CAS  PubMed  Google Scholar 

  116. Guo, Y., Du, J., and Kwiatkowski, D.J., Mol. Cancer Res., 2013, vol. 11, no. 3, p. 282. https://doi.org/10.1158/1541-7786

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  117. De, S., Babu, N.M., Babu, T.M. S., Bhavya Sree, R., Sai Kiran, A., and Reddy, S.K., Mintage J. Pharm. Med. Sci., 2016, vol. 5, no. 2, p. 18.

    CAS  Google Scholar 

  118. Ku, B.M., Bae, Y.H., Koh, J., Sun, J.M., Lee, S.H., Ahn, J.S., Park, K., and Ahn, M.J., Invest New Drugs, 2016, vol. 34, no. 4, p. 407. https://doi.org/10.1007/s10637-016-0350-y

    Article  CAS  PubMed  Google Scholar 

  119. Nicholson, R.I., Gee, J.M.W., and Harper, M.E., Eur. J. Cancer, 2001, vol. 37, p. 9. https://doi.org/10.1016/s0959-8049(01)00231-3

    Article  Google Scholar 

  120. Engelman, J.A., Clin. Cancer Res., 2007, vol. 13, no. 15, p. 4637s. https://doi.org/10.1158/1078-0432.CCR-07-0653

    Article  CAS  Google Scholar 

  121. Brognard, J., Clark, A.S., Ni, Y., and Dennis, P.A., Cancer Res., 2001, vol. 61, no. 10, p. 3986.

    CAS  PubMed  Google Scholar 

  122. Greig, S.L., Drugs, 2016, vol. 76, p. 263. https://doi.org/10.1007/s40265-015-0533-4

    Article  CAS  PubMed  Google Scholar 

  123. Sam, B., Maurice, R.V.F., Richard, A.W., Vasantha, K.K., Reddy, C.C., Andiappan, M., and Heather, M.R., Patent WO 2013014448A1, 2013.

  124. Wang, Y., Wang, L., Guan, S., Cao, W., Wang, H., Chen, Z., Zhao, Y., Yu, Y., Zhang, H., Pang, J.C., Huang, S.L., Akiyama, Y., Yang, Y., Sun, W., Xu, X., Shi, Y., Zhang, H., Kim, E.S., Muscal, J.A., Lu, F., and Yang, J., Sci. Rep., 2016, vol. 6, no. 1, p. 19423. https://doi.org/10.1038/srep19423

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  125. Soda, M., Choi, Y.L., Enomoto, M., Takada, S., Yamashita, Y., Ishikawa, S., Fujiwara, S., Watanabe, H., Kurashina, K., Hatanaka, H., Bando, M., Ohno, S., Ishikawa, Y., Aburatani, H., Niki, T., Sohara, Y., Sugiyama, Y., and Mano, H., Nature, 2007, vol. 448, no. 7153, p. 561. https://doi.org/10.1038/nature05945

    Article  CAS  PubMed  Google Scholar 

  126. Kinoshita, K., Asoh, K., Furuichi, N., Ito, T., Kawada, H., Hara, S., Ohwada, J., Miyagi, T., Kobayashi, T., and Takanashi, K., Bioorg. Med. Chem., 2012, vol. 20, no. 3, p. 1271. https://doi.org/10.1016/j.bmc.2011.12.021

    Article  CAS  PubMed  Google Scholar 

  127. Kinoshita, K., Kobayashi, T., Asoh, K., Furuichi, N., Ito, T., Kawada, H., Hara, S., Ohwada, J., Hattori, K., Miyagi, T., Hong, W.S., Park, M.J., Takanashi, K., Tsukaguchi, T., Sakamoto, H., Tsukuda, T., and Oikawa, N., J. Med. Chem., 2011, vol. 54, no. 18, p. 6286. https://doi.org/10.1021/jm200652u

    Article  CAS  PubMed  Google Scholar 

  128. Newton, A.C., J. Biol. Chem., 1995, vol. 270, no. 48, p. 28495. https://doi.org/10.1074/jbc.270.48.28495

    Article  CAS  PubMed  Google Scholar 

  129. Herbst, R.S., Oh, Y., Wagle, A., and Lahn, M., Clin. Cancer Res., 2007, vol. 13, no. 15, p. 4641s. https://doi.org/10.1158/1078-0432.CCR-07-0538

    Article  CAS  Google Scholar 

  130. McNulty, A.M., Konicek, B.W., Lynch, R.L., Thornton, D., Douglass, L., Colligan, B., Carter, J.H., and Graff, J.R., Cancer Res., 2006, vol. 66, no. 8, p. 314.

    Google Scholar 

  131. Lan, Y., Bai, P., Liu, Y., Afshar, S., Striar, R., Rattray, A.K., Meyer, T.N., Langan, A.G., Posner, A.M., and Shen, S., J. Med. Chem., 2021, vol. 64, no. 20, p. 15420. https://doi.org/10.1021/acs.jmedchem.1c01477

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  132. Duda, P., Akula, S.M., Abrams, S.L., Steelman, L.S., Martelli, A.M., Cocco, L., Ratti, S., Candido, S., Libra, M., Montalto, G., Cervello, M., Gizak, A., Rakus, D,. and McCubrey, J.A., Cells, 2020, vol. 9, no. 5, p. 1110. https://doi.org/10.3390/cells9051110

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  133. Piccirillo, M.C., Bonanno, L., Garassino, M.C., Esposito, G., Dazzi, C., Cavanna, L., Burgio, M.A., Rosetti, F., Rizzato, S., Morgillo, F., Cinieri, S., Veccia, A., Papi, M., Tonini, G., Gebbia, V., Ricciardi, S., Pozzessere, D., Ferro, A., Proto, C., Costanzo, R., D’Arcangelo, M., Proietto, M., Gargiulo, P., Di Liello, R., Arenare, L,. De Marinis, F., Crino, L., Ciardiello, F., Normanno, N., Gallo, C., Perrone, F., Gridelli, C., and Morabito, A., J. Thorac. Oncol., 2022, vol. 17, no. 9, p. 1086. https://doi.org/10.1016/j.jtho.2022.05.008

    Article  CAS  PubMed  Google Scholar 

  134. Li, C.J., Ashwell, M.A., Hill, J., Moussa, M.M., and Munshi, N., Patent EP 1846406B9, 2012.

  135. Lin, B., Song, X., Yang, D., Bai, D., Yao, Y., and Lu, N.A., Gene, 2018, vol. 654, p. 77. https://doi.org/10.1016/j.gene.2018.02.026

    Article  CAS  PubMed  Google Scholar 

  136. Cheng, Y., Wang, Q., Li, K., Shi, J., Liu, Y., Wu, L., Han, B., Chen, G., He, J., and Wang, J., Ann. Oncol., 2019, vol. 30, p. v711. https://doi.org/10.1093/annonc/mdz264.002

  137. Reck, M., Mellemgaard, A., Novello, S., Postmus, P.E., Gaschler-Markefski, B., Kaiser, R., and Buchner, H., Onco. Targets. Ther., 2018, vol. 11, p. 4573. https://doi.org/10.2147/OTT.S170722

    Article  PubMed  PubMed Central  Google Scholar 

  138. Corrales, L., Nogueira, A., Passiglia, F., Listi, A., Caglevic, C., Giallombardo, M., Raez, L., Santos, E., and Rolfo, C., Front. Med., 2017, vol. 4, p. 13. https://doi.org/10.3389/fmed.2017.00013

    Article  Google Scholar 

  139. Fletcher, D.A. and Mullins, R.D., Nature, 2010, vol. 463, no. 7280, p. 485. https://doi.org/10.1038/nature08908

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  140. Naaz, F., Haider, M.R., Shafi, S., and Yar, M.S., Eur. J. Med. Chem., 2019, vol. 171, p. 310. https://doi.org/10.1016/j.ejmech.2019.03.025

    Article  CAS  PubMed  Google Scholar 

  141. Adam, Z., Coupkova, H., Kolek, V., Kucera, M., Loffelmann, L., Martinez, A., Novakova, M., Prusa, P., Reiterer, P., and Skalova, B., Acta Med. Austriaca, 1995, vol. 22, no. 5, p. 120.

    CAS  PubMed  Google Scholar 

  142. Genova, C., Alama, A., Coco, S., Rijavec, E., Dal Bello, M.G., Vanni, I., Biello, F., Barletta, G., Rossi, G., and Grossi, F., Drugs, 2016, vol. 25, no. 12, p. 1447. https://doi.org/10.1080/13543784.2016.1252331

    Article  CAS  Google Scholar 

  143. Zhang, Y., Yang, S.-H., and Guo, X.-L., Biomed. Pharmacother., 2017, vol. 96, p. 659. https://doi.org/10.1016/j.biopha.2017.10.041

    Article  CAS  PubMed  Google Scholar 

  144. Chaniyara, R., Tala, S., Chen, C.-W., Zang, X., Kakadiya, R., Lin, L.-F., Chen, C.-H., Chien, S.-I., Chou, T.-C., Tsai, T.-H., Lee, T.C., Shah, A., and Su, T.L., J. Med. Chem., 2013, vol. 56, no. 4, p. 1544. https://doi.org/10.1021/jm301788a

    Article  CAS  PubMed  Google Scholar 

  145. Barrows, L.R., Radisky, D.C., Copp, B.R., Swaffar, D.S., Kramer, R.A., Warters, R.L., and Ireland, C.M., Anticancer. Drug Des., 1993, vol. 8, no. 5, p. 333.

    CAS  PubMed  Google Scholar 

  146. Lane, A.A. and Chabner, B.A., J. Clin. Oncol., 2009, vol. 27, no. 32, p. 5459. https://doi.org/10.1200/JCO.2009.22.1291

    Article  CAS  PubMed  Google Scholar 

  147. Richon, V.M. and O’Brien, J.P., Clin. Cancer Res., 2002, vol. 8, no. 3, p. 662.

    PubMed  Google Scholar 

  148. Johnstone, R.W., Nat. Rev. Drug Discov., 2002, vol. 1, no. 4, p. 287.

    Article  CAS  PubMed  Google Scholar 

  149. Shinji, C., Maeda, S., Imai, K., Yoshida, M., Hashimoto, Y., and Miyachi, H., Bioorg. Med. Chem., 2006, vol. 14, no. 22, p. 7625. https://doi.org/10.1016/j.bmc.2006.07.008

    Article  CAS  PubMed  Google Scholar 

  150. Han, S., Fukazawa, T., Yamatsuji, T., Matsuoka, J., Miyachi, H., Maeda, Y., Durbin, M., and Naomoto, Y., PLoS One, 2010, vol. 5, no. 11, p. e13834. https://doi.org/10.1371/journal.pone.0013834

  151. Lai, M.-J., Huang, H.-L., Pan, S.-L., Liu, Y.-M., Peng, C.-Y., Lee, H.-Y., Yeh, T.-K., Huang, P.-H., Teng, C.-M., and Chen, C.-S., J. Med. Chem., 2012, vol. 55, no. 8, p. 3777. https://doi.org/10.1021/jm300197a

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  152. Remiszewski, S.W., Sambucetti, L.C., Bair, K.W., Bontempo, J., Cesarz, D., Chandramouli, N., Chen, R., Cheung, M., Cornell-Kennon, S., Dean, K., Diamantidis, G., France, D., Green, M.A., Howell, K.L., Kashi, R., Kwon, P., Lassota, P., Martin, M.S., Mou, Y., Perez, L.B., Sharma, S., Smith, T., Sorensen, E., Taplin, F., Trogani, N., Versace, R., Walker, H., Weltchek-Engler, S., Wood, A., Wu, A., and Atadja, P., J. Med. Chem., 2003, vol. 46, no. 21, p. 4609. https://doi.org/10.1021/jm030235w

    Article  CAS  PubMed  Google Scholar 

  153. Catley, L., Weisberg, E., Tai, Y.-T., Atadja, P., Remiszewski, S., Hideshima, T., Mitsiades, N., Shringarpure, R., LeBlanc, R., Chauhan, D., Munshi, N.C., Schlossman, R., Richardson, P., Griffin, J., and Anderson, K.C., Blood, 2003, vol. 102, no. 7, p. 2615. https://doi.org/10.1182/blood-2003-01-0233

    Article  CAS  PubMed  Google Scholar 

  154. Atadja, P., Gao, L., Kwon, P., Trogani, N., Walker, H., Hsu, M., Yeleswarapu, L., Chandramouli, N., Perez, L., Versace, R., Wu, A., Sambucetti, L., Lassota, P., Cohen, D., Bair, K., Wood, A., and Remiszewski, S., Cancer Res., 2004, vol. 64, no. 2, p. 689. https://doi.org/10.1158/0008-5472.can-03-2043

    Article  CAS  PubMed  Google Scholar 

  155. Cuneo, K.C., Fu, A., Osusky, K., Huamani, J., Hallahan, D.E., and Geng, L., Anticancer Drugs, 2007, vol. 18, no. 7, p. 793. https://doi.org/10.1097/CAD.0b013e3280b10d57

    Article  CAS  PubMed  Google Scholar 

  156. Ellis, L., Bots, M., Lindemann, R.K., Bolden, J.E., Newbold, A., Cluse, L.A., Scott, C.L., Strasser, A., Atadja, P., Lowe, S.W., and Johnstone, R.W., Blood, 2009, vol. 114, no. 2, p. 380. https://doi.org/10.1182/blood-2008-10-182758

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  157. Ahmad, A., Sakr, W.A., and Rahman, K.M.W., Cancers, 2011, vol. 3, no. 3, p. 2955. https://doi.org/10.3390/cancers3032955

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  158. Fischer, E. and Jourdan, F., Ber., 1883, vol. 16, no. 2, p. 2241. https://doi.org/10.1002/cber.188301602141

    Article  Google Scholar 

  159. Ahmad, A., Sakr, W.A., and Rahman, K.M.W., Front. Biosci., 2012, vol. 4, no. 1, p. 410. https://doi.org/10.2741/e388

    Article  Google Scholar 

  160. Sarkar, F.H. and Li, Y., Cancer Treat. Rev., 2009, vol. 35, no. 7, p. 597. https://doi.org/10.1016/j.ctrv.2009.07.001

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  161. Sarkar, F.H., Li, Y., Wang, Z., and Kong, D., Cell. Signal., 2009, vol. 21, no. 11, p. 1541. https://doi.org/10.1016/j.cellsig.2009.03.009

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  162. Moiseeva, E.P., Almeida, G.M., Jones, G.D.D., and Manson, M.M., Mol. Cancer Ther., 2007, vol. 6, no. 11, p. 3071. https://doi.org/10.1158/1535-7163

    Article  PubMed  Google Scholar 

  163. Cover, C.M., Hsieh, S.J., Tran, S.H., Hallden, G., Kim, G.S., Bjeldanes, L.F., and Firestone, G.L., J. Biol. Chem., 1998, vol. 273, no. 7, p. 3838. https://doi.org/10.1074/jbc.273.7.3838

    Article  CAS  PubMed  Google Scholar 

  164. Rahman, K.M.W. and Sarkar, F.H., Cancer Res., 2005, vol. 65, no. 1, p. 364.

    Article  CAS  PubMed  Google Scholar 

  165. Sarkar, F.H. and Li, Y., J. Nutr., 2004, vol. 134, no. 12, p. 3493S. https://doi.org/10.1093/jn/134.12.3493S

    Article  Google Scholar 

  166. Wang, Z., Yu, B.W., Rahman, K.M.W., Ahmad, F., and Sarkar, F.H., Mol. Cancer Ther., 2008, vol. 7, no. 2, p. 341. https://doi.org/10.1158/1535-7163.MCT-07-0476

    Article  CAS  PubMed  Google Scholar 

  167. Sarkar, F.H., Li, Y., Wang, Z., and Kong, D., Int. Rev. Immunol., 2008, vol. 27, no. 5, p. 293. https://doi.org/10.1080/08830180802276179

    Article  CAS  PubMed  Google Scholar 

  168. Li, Y., Ahmad, A., Kong, D., Bao, B. and Sarkar, F.H., Cancer Metastasis Rev., 2014, vol. 33, p. 629. https://doi.org/10.1007/s10555-013-9478-9

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  169. Le, H.T., Schaldach, C.M., Firestone, G.L., and Bjeldanes, L.F., J. Biol. Chem., 2003, vol. 278, no. 23, p. 21136. https://doi.org/10.1074/jbc.M300588200

    Article  CAS  PubMed  Google Scholar 

  170. Ahmad, A., Sakr, W.A., and Rahman, K.M.W., J. Exp. Clin. Med., 2011, vol. 3, no. 2, p. 55. https://doi.org/10.1016/j.jecm.2011.01.001

    Article  CAS  Google Scholar 

  171. Rahman, K.M.W., Banerjee, S., Ali, S., Ahmad, A., Wang, Z., Kong, D., and Sakr, W.A., Cancer Res., 2009, vol. 69, no. 10, p. 4468. https://doi.org/10.1158/0008-5472.CAN-08-4423

    Article  CAS  PubMed  Google Scholar 

  172. Bhatnagar, N., Li, X., Chen, Y., Zhou, X., Garrett, S.H., and Guo, B. Cancer Prev. Res., 2009, vol. 2, no. 6, p. 581. https://doi.org/10.1158/1940-6207.CAPR-08-0142

    Article  CAS  Google Scholar 

  173. Ahmad, A., Kong, D., Sarkar, S.H., Wang, Z., Banerjee, S., and Sarkar, F.H., J. Cell. Biochem., 2009, vol. 107, no. 3, p. 516. https://doi.org/10.1002/jcb.22152

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  174. Kobayashi, H., Nihon Sanka Fujinka Gakkai Zasshi, 1996, vol. 48, no. 8, p. 623.

    CAS  PubMed  Google Scholar 

  175. El Sayed, M., Doctoral Dissertation, Martin Luther University, 2013.

  176. El-Sayed, M.E., Doctoral Dissertation, Halle (Saale), 2013.

  177. Li, Y., Wang, Z., Kong, D., Murthy, S., Dou, Q.P., Sheng, S., Reddy, G.P.V., and Sarkar, F.H., J. Biol. Chem., 2007, vol. 282, no. 29, p. 21542. https://doi.org/10.1074/jbc.M701978200

    Article  CAS  PubMed  Google Scholar 

  178. Gupta, M.K. and Qin, R.-Y. World J. Gastroenterol., 2003, vol. 9, no. 6, p. 1144. https://doi.org/10.3748/wjg.v9.i6.1144

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  179. Khwaja, F.S., Wynne, S., Posey, I., and Djakiew, D., Cancer Prev. Res., 2009, vol. 2, no. 6, p. 566. https://doi.org/10.1158/1940-6207.CAPR-08-0202

    Article  CAS  Google Scholar 

  180. Lei, P., Abdelrahim, M., Cho, S.D., Liu, X., and Safe, S., Mol. Cancer Ther., 2008, vol. 7, no. 10, p. 3363. https://doi.org/10.1158/1535-7163.MCT-08-0439

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  181. Csipo, I., Montel, A.H., Hobbs, J.A., Morse, P.A., and Brahmi, Z., Apoptosis, 1998, vol. 3, p. 105. https://doi.org/10.1023/a:1009696908600

    Article  CAS  PubMed  Google Scholar 

  182. Los, M. and Walczak, H., Caspases: Their Role in Cell Death and Cell Survival, Landes Bioscience, 2002.

  183. Hague, A. and Paraskeva, C., Cell Death Differ., 2004, vol. 11, no. 12, p. 1366. https://doi.org/10.1038/sj.cdd.4401497

    Article  CAS  PubMed  Google Scholar 

  184. https://www.zepzelcapro.com/zepzelca-clinical-data/

  185. https://www.cancerresearchuk.org/about-cancer/cancer-in-general/treatment/cancer-drugs/drugs/sunitinib

  186. Palumbo, A. and Anderson, K., N. Engl. J. Med., 2011, vol. 364, no. 11, p. 1046.

    Article  CAS  PubMed  Google Scholar 

  187. https://www.cancer.gov/publications/dictionaries/cancer-drug/def/serdemetan

  188. https://www.cancer.gov/search/results?swKeyword=Staurosporine

  189. https://hmdb.ca/metabolites/HMDB0015597

  190. https://hmdb.ca/metabolites/HMDB0251702

  191. Ab, O., Bartle, L.M., Rui, L., Coccia, J., Johnson, H.A., Whiteman, K.R., Kellogg, B., Clancy, L., Sun, X., and Goldmacher, V.S., Cancer Res., 2011, vol. 71, no. 8, p. 4576. https://doi.org/10.1158/1538-7445.AM2011-4576

    Article  Google Scholar 

  192. Luban, J., Sattler, R.A., Mühlberger, E., Graci, J.D., Cao, L., Weetall, M., Trotta, C., Colacino, J.M., Bavari, S., Strambio-De-Castillia, C., Suder, E.L., Wang, Y., Soloveva, V., Cintron-Lue, K., Naryshkin, N.A., Pykett, M., Welch, E.M., O’Keefe, K., Kong, R., Goodwin, E., Jacobson, A., Paessler, S., and Peltz, S.W., Virus Res., 2021, vol. 292, p. 198246. https://doi.org/10.1016/j.virusres.2020.198246

    Article  CAS  PubMed  Google Scholar 

  193. Patent CN 108250187A, 2018.

  194. Patent WO 2020002487A1, 2020.

  195. Patent US 2020102299A1, 2020.

  196. Patent CN 109280048A, 2018.

  197. Patent US 9855250B1, 2016.

  198. Patent CN 106496196A, 2016.

  199. Patent WO 2020038433A1, 2020.

  200. Patent WO 2016054987A1, 2016.

  201. Patent CN 110790749A, 2019.

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ACKNOWLEDGMENTS

This work is supported by Department of Chemical Engineering, National Chung Cheng University and the Ministry of Science and Technology of the Republic of China (Taiwan), Department of Pharmaceutical Technology, School of Medical Sciences, Adamas University (India), and Eminent College of Pharmaceutical Technology (India), Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology (India), Department of Pharmaceutical Chemistry, Gupta College of Technological Sciences (India) for providing resources to write this review.

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Sarkar, N., De, S., Das, M. et al. Insights of Indole: A Novel Target in Medicinal Chemistry (A Review). Russ J Gen Chem 93, 1791–1841 (2023). https://doi.org/10.1134/S1070363223070216

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