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Design and Synthesis of Some Heterocyclic Quinoline Derivatives

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Abstract

New quinoline derivatives functionalized with various fused or linked heterocycles were prepared, and their structures were elucidated by IR, NMR, and mass spectra. 2-(Quinolin-8-yloxy)acetohydrazide (QAH) was synthesized starting from quinolin-8-ol and used to obtain pyrazole derivatives by cyclization with ethyl cyanoacetate, ethyl acetoacetate, and benzoylacetone. A series of pyrano[3,2-h]quinoline derivatives fused to pyrimidine and thiazine moieties were obtained via one-pot three-component condensation of 8-hydroxy­quinoline with substituted aromatic aldehydes and malononitrile and ethyl acetoacetate, followed by cyclization with acetic anhydride and ethyl isothiocyanate, respectively.

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REFERENCES

  1. Hu, Y.Q., Gao, C., Zhang, S., Xu, L., Xu, Z., Feng, L.S., Wu, F., and Zhao, F., Eur. J. Med. Chem., 2017, no. 139, p. 22. https://doi.org/10.1016/j.ejmech.2017.07.061

    Article  CAS  PubMed  Google Scholar 

  2. Chung, P.Y., Bian, Z.X., Pun, H.Y., Chan, D., Chan, A.S.C., Chui, C.H., Tang, C.H., and Lam, K.H., Future Med. Chem., 2015, vol. 7, no.7, p. 947. https://doi.org/10.4155/fmc.15.34

    Article  CAS  PubMed  Google Scholar 

  3. Narwal, S., Kumar, S., and Verma, P.K., Res. Chem. Intermed., 2017, vol. 43, no. 5, p. 2765. https://doi.org/10.1007/s11164-016-2794-2802

    Article  CAS  Google Scholar 

  4. Suresh, N., Nagesh, H.N., Sekhar, K.V.G.C., Kumar, A., Shirazi, A.N., and Parang, K., Bioorg. Med. Chem. Lett., 2013, vol. 23, no. 23, p. 6292. https://doi.org/10.1016/j.bmcl.2013.09.077

    Article  CAS  PubMed  Google Scholar 

  5. Hong, D.S., Rosen, P., Lockhart, A.C., Fu, S., Janku, F., Kurzrock, R., Khan, R., Amore, B., Caudillo, I., Deng, H., Hwang, Y.C., Loberg, R., Ngarmchamnan­rith, G., Beaupre, D.M., and Lee, P., Oncotarget, 2015, vol. 6, no. 21, p. 18693. https://doi.org/10.18632/oncotarget.4472

    Article  PubMed  PubMed Central  Google Scholar 

  6. Sharma, V., Kumar Mehta, D., and Das, R., Mini-Rev. Med. Chem., 2017, vol. 17, no. 16, p. 1557. https://doi.org/10.2174/1389557517666170510104954

    Article  CAS  PubMed  Google Scholar 

  7. Wen, X., Wang, S.B., Liu, D.C., Gong, G.H., and Quan, Z.S., Med. Chem. Res., 2015, vol. 24, no. 6, p. 2591. https://doi.org/10.1007/s00044-015-1323-y

    Article  CAS  Google Scholar 

  8. Kumar Gupta, S. and Mishra, A., Anti-Inflammatory Anti-Allergy Agents Med. Chem., 2016, vol. 15, no. 1, p. 31. https://doi.org/10.2174/1871523015666160210124545

    Article  CAS  Google Scholar 

  9. Tempone, A.G., da Silva, A.C., Brandt, C.A., Martinez, F.S., Borborema, S.E., da Silveira, M.A., and de Andrade, H.F., Jr., Antimicrob. Agents Chemother., 2005, vol. 49, no. 3, p. 1076. https://doi.org/10.1128/AAC.49.3.1076-1080.2005

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Nqoro, X., Tobeka, N., and Aderibigbe, B.A., Molecules, 2017, vol. 22, no. 12, article no. 2268. https://doi.org/10.3390/molecules22122268

  11. Shruthi, T.G., Eswaran, S., Shivarudraiah, P., Narayanan, S., and Subramanian, S., Bioorg. Med. Chem. Lett., 2019, vol. 29, no.1, p. 97. https://doi.org/10.1016/j.bmcl.2018.11.002

    Article  CAS  PubMed  Google Scholar 

  12. Desai, N.C., Patel, B.Y., and Dave, B.P., Med. Chem. Res., 2016, vol. 26, p. 109. https://doi.org/10.1007/s00044-016-1732-1736

    Article  Google Scholar 

  13. Dubé, D., Blouin, M., Brideau, C., Chan, C.C., Desmarais, S., Ethier, D., Falgueyret, J.-P., Friesen, R.W., Girard, M., Girard, Y., Guay, J., Riendeau, D., Tagari, P., and Young, R.N., Bioorg. Med. Chem. Lett., 1998, vol. 8, no.10, p. 1255. https://doi.org/10.1016/s0960-894x(98)00201-7

    Article  PubMed  Google Scholar 

  14. Maguire, M.P., Sheets, K.R., McVety, K., Spada, A.P., and Zilberstein, A., J. Med. Chem., 1994, vol. 37, no. 14, p. 2129. https://doi.org/10.1021/jm00040a003

    Article  CAS  PubMed  Google Scholar 

  15. Jin, X.Y., Chen, H., Li, D.D., Li, A.L., Wang, W.Y., and Gu, W., J. Enzyme Inhib. Med. Chem., 2019, vol. 34, no. 1, p. 955. https://doi.org/10.1080/14756366.2019.1605364

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Bhardwaj, N., Choudhary, D., Pathania, A., Baranwal, S., and Kumar, P., Turk. J. Chem., 2020, vol. 44, no. 6, p. 1623. https://doi.org/10.3906/kim-2004-14

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. https://www.drugs.com/newdrugs/fda-approves-xtoro-finafloxacin-otic-suspension-swimmer-s-ear-4127.html

  18. Maini, K., Gould, H., Hicks, J., Iqbal, F., Patterson, J., Edinoff, A.N., Cornett, E.M., Kaye, A.M., Viswa­nath, O., Urits, I., and Kaye, A.D., Neurol. Int., 2021, vol. 1, no. 13, p. 279. https://doi.org/10.3390/neurolint13030029

    Article  Google Scholar 

  19. Marella, A., Tanwar, O.P., Saha, R., Ali, M.R., Srivastava, S., Akhter, M., Shaquiquzzaman, M., and Alam, M.M., Saudi Pharm. J., 2013, vol. 21, no. 1, p. 1. https://doi.org/10.1016/j.jsps.2012.03.002

    Article  PubMed  Google Scholar 

  20. Mao, M., Zhang, X., Zhu, B., Wang, J., Wu, G., Yin, Y., and Song, Q., Dyes Pigm., 2016, vol. 124, p. 72. https://doi.org/10.1016/j.dyepig.2015.09.002

    Article  CAS  Google Scholar 

  21. Mongal, B.N., Pal, A., Mandal, T.K., Datta, J., and Naskar, S., Polyhedron, 2015, no. 102, p. 615. https://doi.org/10.1016/j.poly.2015.10.040

    Article  CAS  Google Scholar 

  22. Kim, J.I., Shin, I.S., Kim, H., and Lee, J.K., J. Am. Chem. Soc., 2005, vol. 127, no. 6, p. 1614. https://doi.org/10.1021/ja043721x

    Article  CAS  PubMed  Google Scholar 

  23. Althobiti, H.A. and Zabin, S.A., Open Chem., 2020, vol. 18, no. 1, p. 591. https://doi.org/10.1515/chem-2020-0085

    Article  CAS  Google Scholar 

  24. Kourat, O., Djafri, A., Benhalima, N., Megrouss, Y., Belkafouf, N., Rahmani, R., Daran, J., Djafri, A., and Chouaih. A., J. Mol. Struct., 2020, vol. 1222, article ID 128952. https://doi.org/10.1016/j.molstruc.2020.128952

  25. Asiri, Y.I., Muhsinah, A.B., Alsayari, A., Venkatesan, K., Al-Ghorbani, M., and Mabkhot, Y.N., Bioorg. Med. Chem. Lett., 2021, vol. 44, article ID 128117. https://doi.org/10.1016/j.bmcl.2021.128117

  26. Bin Muhsinah, A., Alsayari, A., Asiri, Y.I., Venkate­san, K., Al-Ghorbani, M., and Mabkhot, Y.N., Polycyclic Aromat. Compd., 2022, vol. 42, no. 8, p. 5261. https://doi.org/10.1080/10406638.2021.1933104

    Article  CAS  Google Scholar 

  27. Al-Ghorbani, M., Pavankumar, G.S., Naveen, P., Thirusangu, P., Prabhakar, B.T., and Khanum, S.A., Bioorg. Chem., 2016, vol. 65, p. 110. https://doi.org/10.1016/j.bioorg.2016.02.006

    Article  CAS  PubMed  Google Scholar 

  28. Al‐Ghorbani, M. and Gouda, M.A., J. Heterocycl. Chem., 2020, vol. 57, no. 8, p. 3213. https://doi.org/10.1002/jhet.4041

    Article  CAS  Google Scholar 

  29. Gouda, M.A., Al‐Ghorbani, M., and Al‐Zaqri, N., J. Heterocycl. Chem., 2020, vol. 57, no. 10, p. 3664. https://doi.org/10.1002/jhet.4085

    Article  CAS  Google Scholar 

  30. Al-Ghorbani, M., Rekha, N.D., Ranganatha, V.L., Prashanth, T., Veerabasappagowda, T., and Khanum, S.A., Russ. J. Bioorg. Chem., 2015, vol. 41, no. 5, p. 619. https://doi.org/10.7868/s0132342315040028

    Article  CAS  Google Scholar 

  31. Rbaa, M., Hichar, A., Dohare, P., Anouar, E.H., Lakhrissi, Y., Lakhrissi, B., Berredjem, M., Almalki, F., Rastija, V., Rajabi, M., Ben Hadda, T., and Zarrouk, A., Arab. J. Sci. Eng., 2021, vol. 46, no. 6, p. 5533. https://doi.org/10.1007/s13369-020-05089-y

    Article  CAS  Google Scholar 

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Funding

The author thanks Taibah University for financial support.

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Authors and Affiliations

  1. Department of Chemistry, College of Science and Arts, Ulla, Taibah University, 41477, Medina Mnora, Saudi Arabia

    M. Al-Ghorbani

  2. Department of Chemistry, College of Education, Thamar University, 87246, Dhamar, Yemen

    M. Al-Ghorbani

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  1. M. Al-Ghorbani
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Correspondence to M. Al-Ghorbani.

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Al-Ghorbani, M. Design and Synthesis of Some Heterocyclic Quinoline Derivatives. Russ J Org Chem 58, 1272–1279 (2022). https://doi.org/10.1134/S1070428022090123

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  • DOI: https://doi.org/10.1134/S1070428022090123

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