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A Review on Chemical and Biological Studies of 4-Chromanone Derivatives

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Abstract

The chroman-4-one skeleton is a remarkable structural system that belongs to oxygen-containing heterocycles. It constitutes a major building block in a large class of medicinal compounds, and synthetic chroman-4-one derivatives exhibit a broad spectrum of significant biological and pharmaceutical activities. This review article highlights the synthesis and reactions of 4-chromanone derivatives possessing important pharmaceutical activities.

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REFERENCES

  1. Fridén-Saxin, M., Pemberton, N., Andersson, K.S., Dyrager, C., Friberg, A., Grøtli, M., and Luthman, K., J. Org. Chem., 2009, vol. 7, p. 2755. https://doi.org/10.1021/jo802783z

    Article  CAS  Google Scholar 

  2. Khan, M.K., Zill-E-Huma, and Dangles, O., J. Food Compos. Anal., 2014, vol. 33, p. 85. https://doi.org/10.1016/j.jfca.2013.11.004

    Article  CAS  Google Scholar 

  3. Křížová, L., Dadáková, K., Kašparovská J., and Kašparovský, T., Molecules, 2019, vol. 24, article no. 1076. https://doi.org/10.3390/molecules24061076

  4. Ghatpande, N.G., Jadhav, J.S., Kaproormath, R.V., Soliman M.E., and Shaikh, M.M., Bioorg. Med. Chem., 2020, vol. 28, article ID 115813. https://doi.org/10.1016/j.bmc.2020.115813

  5. Shaikh, N.S., Kushalappa, Y.M., Sheshappa, S.P., and Nagaraju, H.H., ChemistrySelect, 2019, vol. 4, p. 13029. https://doi.org/10.1002/slct.201903862

    Article  Google Scholar 

  6. Reis, J., Gaspar, A., Milhazes, N., and Borges, F., J. Med. Chem., 2017, vol. 60, p. 7941. https://doi.org/10.1021/acs.jmedchem.6b01720

    Article  CAS  PubMed  Google Scholar 

  7. Nibbs, A.E. and Scheidt, K.A., Eur. J. Org. Chem., 2012, vol. 2012, no. 3, p. 449. https://doi.org/10.1002/ejoc.201101228

    Article  CAS  Google Scholar 

  8. Albrecht, U., Lalk, M., and Langer, P., Bioorg. Med. Chem., 2005, vol. 13, p. 1531. https://doi.org/10.1016/j.bmc.2004.12.031

    Article  CAS  PubMed  Google Scholar 

  9. Di Pisa, F., Landi, G., Iacono, L.D., Pozzi, C., Borsari, C., Ferrari, S., Santucci, M., Santarem, N., Cordeiro-da-Silva, A., Moraes, C.B., Alcantara, L.M., Fontana, V., Freitas-Junior, L.H., Gul, S., Kuzikov, M., Behrens, B. Pöhner, I., Wade, R.C., Paola Costi, M., and Mangani, S., Molecules, 2017, vol. 22, article no. 426. https://doi.org/10.3390/molecules22030426

  10. Seifert, T., Malo, M., Kokkola, T., Engen, K., Fridén-Saxin, M., Wallén, E.A.A., Lahtela-Kakkonen, M., Jarho, E.M., and Luthman, K., J. Med. Chem., 2014, vol. 57, p. 9870. https://doi.org/10.1021/jm500930h

    Article  CAS  PubMed  Google Scholar 

  11. Kumar, D., Sharma, P., Singh, H., Nepali, K., Gupta, G.K., Jaina, S.K., and Ntie-Kang, F., RSC Adv., 2017, vol. 7, p. 36977. https://doi.org/10.1039/C7RA05441F

    Article  CAS  Google Scholar 

  12. McKee, T.C., Bokesch, H.R., McCormick, J.L., Rashid, M.A., Spielvogel, D., Gustafson, K.R., Ala­vanja, M.M., Cardellina, J.H., and Boyd, M.R., J. Nat. Prod., 1997, vol. 60, p. 431. https://doi.org/10.1021/np970031g

    Article  CAS  PubMed  Google Scholar 

  13. Fridén-Saxin, M., Seifert, T., Landergren, M.R., Suuronen, T., Lahtela-Kakkonen, M., Jarho, E.M., and Luthman, K., J. Med. Chem., 2012, vol. 55, p. 7104. https://doi.org/10.1021/jm3005288

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Zhong, Y., Boruta, D.T., Gauthier, D.R., and Askin, D., Tetrahedron Lett., 2011, vol. 52, p. 4824. https://doi.org/10.1016/j.tetlet.2011.07.018

    Article  CAS  Google Scholar 

  15. Shynkar, V.V., Klymchenko, A.S., Piémont, E., Demchenko, A.P., and Mély, Y., J. Phys. Chem., 2004, vol. 108, p. 8151. https://doi.org/10.1021/jp047990l

    Article  CAS  Google Scholar 

  16. Diana, E.J., Kanchana, U.S., and Mathew, T.V., Org. Biomol. Chem., 2021, vol. 19, p. 7995. https://doi.org/10.1039/D1OB01352A

    Article  CAS  PubMed  Google Scholar 

  17. Raoof, M.R.Y., Iraqi J. Sci., 2013, vol. 24, p. 32. https://doi.org/10.33899/rjs.2013.78757

    Article  Google Scholar 

  18. Zhong, Y.-L., Boruta, D.T., Gauthier, D.R., Jr., and Askin, D., Tetrahedron Lett., 2011, vol. 52, no. 38, p. 4824. https://doi.org/10.1016/j.tetlet.2011.07.018

    Article  CAS  Google Scholar 

  19. Morales, P., Azofra, L.M., Cumella, J., Hernandez-Folgado, L., Roldán, M., Alkorta, I., and Jagerovic, N., Arkivoc, 2014, part (ii), p. 319. https://doi.org/10.3998/ark.5550190.p008.246

  20. Reddy, E.V., Hariprasad, K.S., Zehra, A., Vijaykumar, P., Tiwari, A.K., Addlagatta, A., and Raju, B.C., Indian J. Chem., Sect. B, 2019, vol. 58, p. 680.

    Google Scholar 

  21. El Malah, T., Shamroukh, A.H., Kotb, E.R., Soliman, H.A., Mahmoud, K., and Hegab, M.I., Phosphorus, Sulfur Silicon Relat. Elem., 2021, vol. 196, p. 970. https://doi.org/10.1080/10426507.2021.1947275

    Article  CAS  Google Scholar 

  22. Hegab, M.I., Morsy, E.M.H., Abd El-Mageed, A.E., Ali, M.M., El-Senousy, W.M., Tolan, H.E.M., Gad, F.A., and Abdel-Megeid, F.M.E., Phosphorus, Sulfur Silicon Relat. Elem., 2015, vol. 190, p. 1901. https://doi.org/10.1080/10426507.2015.1032410

    Article  CAS  Google Scholar 

  23. Kabbe, H.J., Synthesis, 1978, vol. 1978, no. 12, p. 886. https://doi.org/10.1055/s-1978-24924

    Article  Google Scholar 

  24. Gabbutt, C.D., Hepworth, J.D., and Heron, B.M., Tetrahedron, 1994, vol. 50, p. 5245. https://doi.org/10.1016/S0040-4020(01)90434-X

    Article  CAS  Google Scholar 

  25. Brogden, P.J. and Hepworth, J.D., J. Chem. Soc., Perkin Trans. 1, 1983, p. 827. https://doi.org/10.1039/p19830000827

  26. Feng, L., Maddox, M.M., Alam, M.Z., Tsutsumi, L.S., Narula, G., Bruhn, D.F., Wu, X., Sandhaus, S., Lee, R.B., Simmons, C.J., Tse-Dinh, Y.-C., Hurdle, J.G., Lee, R.E., and Sun, D., J. Med. Chem., 2014, vol. 57, p. 8398. https://doi.org/10.1021/jm500853v

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. Zhao, J., Li, P., Li, X., Xia, C., and Li, F., Chem. Commun., 2016, vol. 52, p. 3661. https://doi.org/10.1039/C5CC09730D

    Article  CAS  Google Scholar 

  28. Yang, W.C., Dai, P., Luo, K., Ji, Y.G., and Wu, L., Adv. Synth. Catal., 2017, vol. 359, p. 2390. https://doi.org/10.1002/adsc.201601407

    Article  CAS  Google Scholar 

  29. Lu, D., Wan, Y., Kong, L., and Zhu, G., Org. Lett., 2017, vol. 19, p. 2929. https://doi.org/10.1021/acs.orglett.7b00095

    Article  CAS  PubMed  Google Scholar 

  30. Jung, S., Kim, J., and Hong, S., Adv. Synth. Catal., 2017, vol. 359, p. 3945. https://doi.org/10.1002/adsc.201701072

    Article  CAS  Google Scholar 

  31. Hu, H., Chen, X., Sun, K., Wang, J., Liu, Y., Liu, H., Yu, B., Sun, Y., Qu, L., and Zhao, Y., Org. Chem. Front., 2018, vol. 5, p. 2925. https://doi.org/10.1039/C8QO00882E

    Article  CAS  Google Scholar 

  32. Hu, H., Chen, X., Sun, K., Wang, J., Liu, Y., Liu, H., Fan, L., Yu, B., Sun, Y., Qu, L., and Zhao, Y., Org. Lett., 2018, vol. 20, p. 6157. https://doi.org/10.1021/acs.orglett.8b02627

    Article  CAS  PubMed  Google Scholar 

  33. Sheng, J., Liu, J., Chen, L., Zhang, L., Zheng, L., and Wei, X., Org. Chem. Front., 2019, vol. 6, p. 1471. https://doi.org/10.1039/C9QO00292H

    Article  CAS  Google Scholar 

  34. Liu, Q., Xie, G., Wang, Q., Moa, Z., Lia, C., Ding, S., and Wang, X., Tetrahedron, 2019, vol. 75, p. article ID 130490. https://doi.org/10.1016/j.tet.2019.130490

  35. Zhou, N., Wu, M., Zhang, M., and Zhou, X., Asian J. Org. Chem., 2019, vol. 8, p. 828. https://doi.org/10.1002/ajoc.201900121

    Article  CAS  Google Scholar 

  36. Xiao, Y.M., Liu, Y., Mai, W.P., Mao, P., Yuan, J.W., and Yang, L.R., ChemistrySelect, 2019, vol. 4, p. 1939. https://doi.org/10.1002/slct.201900147

    Article  CAS  Google Scholar 

  37. He, X.K., Cai, B.G., Yang, Q.Q., Wang, L., and Xuan, J., Chem. Asian J., 2019, vol. 14, p. 3269. https://doi.org/10.1002/asia.201901078

    Article  CAS  PubMed  Google Scholar 

  38. Li, G.H., Han, Q.Q., Sun, Y.Y., Chen, D., Wang, Z., Xu, X., and Yu, X., Chin. Chem. Lett., 2020, vol. 31, p. 3255. https://doi.org/10.1016/j.cclet.2020.03.007

    Article  CAS  Google Scholar 

  39. Liu, Q., Lu, W., Xie, G., and Wang, X., Beilstein J. Org. Chem., 2020, vol. 16, p. 1974. https://doi.org/10.3762/bjoc.16.164

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. Huang, H.-L., Du, J.-Y., Li, Q.-L., Gao, F., and Ma, C.-L., J. Org. Chem., 2020, vol. 85, p. 3963. https://doi.org/10.1021/acs.joc.9b03253

    Article  CAS  PubMed  Google Scholar 

  41. Mei, Y., Zhao, L., Liu, Q., Ruan, S., Wang, L., and Li, P., Green Chem., 2020, vol. 22, p. 2270. https://doi.org/10.1039/D0GC00009D

    Article  CAS  Google Scholar 

  42. Das, S., Parida, S.K., Mandal, T., Sing, L., De Sarkar, S., and Murarka, S., Chem. Asian J., 2020, vol. 15, p. 568. https://doi.org/10.1002/asia.201901735

    Article  CAS  PubMed  Google Scholar 

  43. Han, Q.-Q., Li, G.-H., Sun, Y.-Y., Chen, D.-M., Wang, Z.-L., Yu, X.-Y., and Xu, X.-M., Tetrahedron Lett., 2020, vol. 61, article ID 151704. https://doi.org/10.1016/j.tetlet.2020.151704

  44. Wang, N.-X., Xing, Y., and Wang, Y.-J., Curr. Org. Chem., 2013, vol. 17, p. 1555. https://doi.org/10.2174/1385272811317140010

    Article  CAS  Google Scholar 

  45. Du, X.-W. and Stanley, L.M., Org. Lett., 2015, vol. 17, p. 3276. https://doi.org/10.1021/acs.orglett.5b01447

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  46. Jhuang, H.S., Reddy, D.M., Chen, T.-H., and Lee, C.F., Asian J. Org. Chem., 2016, vol. 5, p. 1452. https://doi.org/10.1002/ajoc.201600423

    Article  CAS  Google Scholar 

  47. Chang, M.-Y., Wu, Y.-S., and Chen, H.-Y., Org. Lett., 2018, vol. 20, p. 1824. https://doi.org/10.1021/acs.orglett.8b00316

    Article  CAS  PubMed  Google Scholar 

  48. Zhou, Y., Xiong, Z., Qiu, J., Kong, L., and Zhu, G., Org. Chem. Front., 2019, vol. 6, p. 1022. https://doi.org/10.1039/C9QO00136K

    Article  CAS  Google Scholar 

  49. Xie, Z.-Z., Deng, Z.-X., Zheng, Y., Chen, Y.-S., Xiao, J.-A., Chen, K., and Xiang, H.-Y., Org. Biomol. Chem., 2020, vol. 18, p. 8916. https://doi.org/10.1039/D0OB01588A

    Article  CAS  PubMed  Google Scholar 

  50. Dzieszkowski, K. and Rafiński, Z., Adv. Synth. Catal., 2020, vol. 362, p. 3830. https://doi.org/10.1002/adsc.202000550

    Article  CAS  Google Scholar 

  51. Takao, K., Yamashita, M., Yashiro, A., and Sugita, Y., Chem. Pharm. Bull., 2016, vol. 64, p. 1203. https://doi.org/10.1248/cpb.c16-00327

    Article  CAS  Google Scholar 

  52. Kumar, S. and Makrandi, J.K., E-J. Chem., 2012, vol. 9, p. 1251. https://doi.org/10.1155/2012/324907

    Article  CAS  Google Scholar 

  53. Wang, R., Liu, Z., Du, L., and Li, M., Drug Discoveries Ther., 2014, vol. 8, p. 76. https://doi.org/10.5582/ddt.8.76

    Article  CAS  Google Scholar 

  54. Hegab, M.I., Amr, A.E.-G.A., and Abdel-Megeid, F.M.E., Z. Naturforsch., Teil B, 2002, vol. 57, p. 922. https://doi.org/10.1515/znb-2002-0813

    Article  CAS  Google Scholar 

  55. Hegab, M.I., Rashad, A.E., Shamroukh, A.H., and Ham­za, I.A., J. Sulfur Chem., 2006, vol. 27, no. 3, p. 213. https://doi.org/10.1080/17415990600622620

    Article  CAS  Google Scholar 

  56. Chen, H., Xing, Y., Xie, J., Xie, J., Xing, D., Tang, J., Yang, F., Yi, Z., and Qiu, W.-W., RSC Adv., 2019, vol. 9, p. 33794. https://doi.org/10.1039/C9RA06420F

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  57. Letafat, B., Shakeri, R., Emami, S., Noushini, S., Hosseini, N.M., Shirkavand, N., Ardestani, S.K., Safavi, M., Samadizadeh, M., Letafat, A., Shafiee, A., and Foroumadi, A., Iran. J. Basic Med. Sci., 2013, vol. 16, no. 11, p. 1155. https://doi.org/10.22038/IJBMS.2013.1933

    Article  PubMed  PubMed Central  Google Scholar 

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  1. Photochemistry Department, National Research Centre, Dokki, 12622, Giza, Egypt

    M. I. Hegab

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Hegab, M.I. A Review on Chemical and Biological Studies of 4-Chromanone Derivatives. Russ J Org Chem 59, 483–497 (2023). https://doi.org/10.1134/S107042802303017X

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