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3-Aryl/Heteryl-5-Phenylindeno[1,2-d]thiazolo[3,2-a]pyrimidin-6(5H)-ones: Synthesis, Characterization, and Antimicrobial Investigation

Abstract

Discovery towards the potent antimicrobial agents is indispensable for the treatment of infections caused by resistant microbes. Thus, we prepared a novel series of 3-substituted 5-phenylindeno-thiazolopyrimidinone derivatives following conventional method. All the molecules were investigated for their in vitro antimicrobial potency against different bacteria and fungi, and the results were compared with streptomycin and clotrimazole standard drugs, respectively. Among the twelve analogs, 4-methoxyphenyl-5-phenylindeno[1,2-d]thiazolo[3,2-a]pyrimidin-6(5H)-one showed equipotent activity against a bacterium, Staphylococcus aureus (minimum inhibitory concentration 25 µg/mL and zone of inhibition 22 mm), and a fungus, Aspergillus niger (zone of inhibition 20 mm). The rest of the thiazolo[3,2-a]pyrimidin-6(5H)-one derivatives exhibited week to reasonable activities against the tested bacterial and fungal strains.

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REFERENCES

  1. Guo, H., Eur. J. Med. Chem., 2019, vol. 164, pp. 678–688.

    CAS  PubMed  Google Scholar 

  2. Furst, A.L. and Francis, M.B., Chem. Rev., 2019, vol. 119, pp. 700–726.

    CAS  PubMed  Google Scholar 

  3. Zhang, B., Eur. J. Med. Chem., 2019, vol. 168, pp. 357–372.

    CAS  PubMed  Google Scholar 

  4. Richardson, L.A., PLoS Biol., 2017, vol. 15, p. e2 003 775.

    Google Scholar 

  5. Naylor, N.R., Atun, R., Zhu, N., Kulasabanathan, K., Silva, S., Chatterjee, A., Knight, G.M., and Robotham, J.V., Antimicrob. Resist. Infect. Control., 2018, vol. 7, p. 58.

    PubMed  PubMed Central  Google Scholar 

  6. Davies, J. and Davies, D., Microbiol. Mol. Biol. Rev., 2010, vol. 74, pp. 417–433.

    CAS  PubMed  PubMed Central  Google Scholar 

  7. Janardhan, B., Manjulatha, K., Srinivas, B., Rajitha, B., Muralikrishna, N., and Sadanandam, A., RSC Adv., 2014, vol. 4, pp. 22 866–22 874.

    Google Scholar 

  8. Dong, C., Zhi-Hua, Z., Yu, C., Xin-Jia, Y., Shi-Ti, Z., Liang-Jing, Z., Li-Hong, M., Fang, L., and Bing-Jie, F., Med. Chem. Res., 2016, vol. 25, pp. 292–302.

    Google Scholar 

  9. Ashok, M., Holla, B.S., and Kumari, N.S., Eur. J. Med. Chem., 2007, vol. 42, pp. 380–385.

    CAS  PubMed  Google Scholar 

  10. Pan, B., Huang, R., Zheng, L., Chen, C., Han, S., Qu, D., Zhu, M., and Wei, P., Eur. J. Med. Chem., 2011, vol. 46, pp. 819–824.

    CAS  PubMed  Google Scholar 

  11. Suresh, L., Sagar Vijay Kumar, P., Poornachandra, Y., Ganesh Kumar, C., Babu, N.J., and Chandramouli, G.V., Bioorg. Med. Chem., 2016, vol. 24, pp. 3808–3817.

    CAS  PubMed  Google Scholar 

  12. Hassan, G.S., El-Messery, S.M., and Abbas, A., Bioorg. Chem., 2017, vol. 74, pp. 41–52.

    CAS  PubMed  Google Scholar 

  13. Holla, B.S., Rao, B.S., Sarojini, B.K., and Akberali, P.M., Eur. J. Med. Chem., 2004, vol. 39, pp. 777–783.

    CAS  PubMed  Google Scholar 

  14. Mohamed, S.F., Flefel, E.M., Amr, Ael-G., and Abd El-Shafy, D.N., Eur. J. Med. Chem., 2010, vol. 45, pp. 1494–1501.

    CAS  PubMed  Google Scholar 

  15. Abdel Moty, S.G., Hussein, M.A., Abdel Aziz, S.A., and Abou-Salim, M.A., Saudi Pharm. J., 2016, vol. 24, pp. 119–132.

    PubMed  Google Scholar 

  16. Ramesh, L.S., Charusheela, A.B., and Jyothi, B.W., Med. Chem. Res., 2013, vol. 22, pp. 1884–1892.

    Google Scholar 

  17. Tozkoparan, B., Ertan, M., Kelicen, P., and Demirdamar, R., Farmaco, 1999, vol. 54, pp. 588–593.

    CAS  PubMed  Google Scholar 

  18. Tozkoparan, B., Ertan, M., Krebs, B., Lage, M., Kelicen P., and Demirdamar, R., Arch. Pharm., 1998, vol. 331, pp. 201–206.

    CAS  Article  Google Scholar 

  19. Al-Omary, F.A., Hassan, G.S., EI-Messery, S.M., and EI-Subbagh, H.I., Eur. J. Med. Chem., 2012, vol. 47, pp. 65–72.

    CAS  PubMed  Article  Google Scholar 

  20. Fatima, S., Sharma, A., Saxena, R., Tripathi, R., Shukla, S.K., Pandey, S.K., Tripathi, R., and Tripathi, R.P., Eur. J. Med. Chem., 2012, vol. 55, pp. 195–204.

    CAS  PubMed  Google Scholar 

  21. Danel, K., Pedersen, E.B., and Nielsen, C., J. Med. Chem., 1998, vol. 41, pp. 191–198.

    CAS  PubMed  Google Scholar 

  22. Maddila, S., Damu, G., Oseghe, E., Abafe, O., Rao, C.V., and Lavanya, P., J. Korean Chem. Soc., 2012, vol. 56, pp. 334–340.

    CAS  Google Scholar 

  23. Balkan, A., Uma, S., Ertan, M., and Wiegrebe, W., Pharmazie., 1992, vol. 47, pp. 687–688.

    CAS  PubMed  Google Scholar 

  24. Liu, S., Shang, R., Shi, L., Wan, D.C., and Lin, H., Eur. J. Med. Chem., 2014, vol. 81, pp. 237–244.

    CAS  PubMed  Google Scholar 

  25. Hui, Z., Lan-mei, C., Lin-lin, Z., Si-jie, L., David, C.C.W., Huang-quan, L., and Chun, H., Arkivoc, 2008, vol. xiii, pp. 266–277.

    Google Scholar 

  26. Kolb, S., Mondesert, O., Goddard, M.L., Jullien, D., Villoutreix, B.O., Ducommun, B., Garbay, C., and Braud, E., ChemMedChem., 2009, vol. 4, pp. 633–648.

    CAS  PubMed  Google Scholar 

  27. Khobragade, C.N., Bodade, R.G., Dawane, B.S., Konda, S.G., and Khandare, N.T., J. Enzyme Inhib. Med. Chem., 2010, vol. 25, pp. 615–621.

    CAS  PubMed  Google Scholar 

  28. Feng, Y., Ding, X., Chen, T., Chen, L., Liu, F., Jia, X., Luo, X., Shen, X., Chen, K., Jiang, H., Wang, H., Liu, H., and Liu, D., J. Med. Chem., 2010, vol. 53, pp. 3465–3479.

    CAS  PubMed  Google Scholar 

  29. El-Bayouki, K.A. and Basyouni, W.M., J. Sulfur Chem., 2010, vol. 31, pp. 551–590.

    CAS  Google Scholar 

  30. Nagarajaiah, H., Khazi, I., and Begum, N.S., J. Chem. Sci., 2012, vol. 124, pp. 847–855.

    CAS  Google Scholar 

  31. Kappe, C.O., Eur. J. Med. Chem., 2000, vol. 35, pp. 1043–1052.

    CAS  PubMed  Google Scholar 

  32. Quan, Z.J., Zhang, Z., Wang, J.K., Wang, X.C., Liu, Y.J., and Ji, P.Y., Heteroat. Chem., 2008, vol. 19, pp. 149–153.

    CAS  Google Scholar 

  33. Bozsing, D., Sohar, P., Gigler, G., and Kovacs, G., Eur. J. Med. Chem., 1996, vol. 31, pp. 663–668.

    CAS  Google Scholar 

  34. Kulakovi, I.V., Nurkenovi, O.A., Turdybekov, D.M., Issabaevai, G.M., Mahmutova, A.S., and Turdybekov, K.M., Chem. Heterocycl. Compd., 2009, vol. 45, pp. 856–859.

    Google Scholar 

  35. Gali, R., Banothu, J., Porika, M., Velpula, R., Hnamte, S., Bavantula, R., Abbagani, S., and Busi, S., Bioorg. Med. Chem. Lett., 2014, vol. 24, pp. 4239–4242.

    CAS  PubMed  Google Scholar 

  36. Gali, R., Banothu, J., Gondru, R., Bavantula, R., Velivela, Y., and Crooks, P.A., Bioorg. Med. Chem. Lett., 2015, vol. 25, pp. 106–112.

    CAS  PubMed  Google Scholar 

  37. Gondru, R., Peddi, S.R., Manga, V., Khanapur, M., Gali, R., Sirassu, N., and Bavantula, R., Mol. Divers., 2018, vol. 22, pp. 943–956.

    CAS  PubMed  Google Scholar 

  38. Sahu, S.K., Mishra, A., and Behera, R.K., Indian J. Heterocycl. Chem., 1996, vol. 6, pp. 91–94.

    CAS  Google Scholar 

  39. Semra, I., Filiz, S., and Ferdag, C., Int. J. Nat. Eng. Sci., 2007, vol. 1, pp. 59–61.

    Google Scholar 

  40. Mert, S., Kasimogullari, R., Ica, T., Colak, F., Altun, A., and Ok, S., Eur. J. Med. Chem., 2014, vol. 78, pp. 86–96.

    CAS  PubMed  Google Scholar 

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ACKNOWLEDGMENTS

The authors are grateful to Dr. Busi Siddhardha, Department of microbiology, Pondicherry University, for antimicrobial screening. Dr. Rajitha thanks the Department of Chemistry, Gayatri Vidya Parishad College of Engineering (A), A.P., for providing research facilities.

Funding

Arya C.G. thanks the MHRD for providing financial support.

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Correspondence to B. Janardhan.

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This article does not contain any studies involving animals or human participants performed by any of the authors.

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The authors declare that they have no conflict of interest.

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Corresponding author: phone: 0091-0891-2535788; e-mail: janardhan@nitc.ac.in.

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Rajitha, G., Arya, C.G., Janardhan, B. et al. 3-Aryl/Heteryl-5-Phenylindeno[1,2-d]thiazolo[3,2-a]pyrimidin-6(5H)-ones: Synthesis, Characterization, and Antimicrobial Investigation. Russ J Bioorg Chem 46, 612–619 (2020). https://doi.org/10.1134/S106816202004007X

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Keywords:

  • antimicrobial activity
  • 3-(bromoacetyl)coumarin
  • 1,3-indandione
  • phenacyl bromide
  • thiazolopyrimidinone