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Vol. 36 No. 2 (2024): Vol 36 Issue 2, 2024

Copyright (c) 2024 Bhargavi Posinasetty, Rajasekhar Komarla Kumarachari , Prashanti Chitrapu , Jyothirmayee Devineni , Sudhahar Dharmalingam , Chilamakuru Naresh Babu, Jayendra Kumar

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Synthesis, Antimicrobial Activity and Molecular Docking of Some Novel 2-Aryl-4H-[1,3]-thiazolo[4,5-b]indoles

https://doi.org/10.14233/ajchem.2024.30986
Bhargavi Posinasetty
Department of Public Health, University of Southern Mississippi, MS-39406, USA Department of Dentistry, Government Dental College and Research Institute, Bellary-583104, India
https://orcid.org/0009-0004-3220-5219
Rajasekhar Komarla Kumarachari
Department of Pharmaceutical Chemistry, Sri Padmavathi School of Pharmacy, Tiruchanur, Tirupati-517503, India
https://orcid.org/0000-0001-5611-1410
Prashanti Chitrapu
Vision College of Pharmaceutical Sciences and Research, Secunderabad-500092, India
https://orcid.org/0000-0002-9665-365X
Jyothirmayee Devineni
Department of Pharmaceutics and Biotechnology, KVSR Siddhartha College of Pharmaceutical Sciences, Vijayawada-520010, India
https://orcid.org/0000-0002-4549-2550
Sudhahar Dharmalingam
Department of Pharmaceutical Chemistry and Analysis, Nehru College of Pharmacy, Thiruvilwamala-680588, India
https://orcid.org/0009-0007-7598-8446
Chilamakuru Naresh Babu
Raghavendra Institute of Pharmaceutical Education and Research, Ananthapuramu-515721, India
https://orcid.org/0000-0002-8496-053X
Jayendra Kumar
SRM Modinagar College of Pharmacy, SRM Institute of Science and Technology Delhi-NCR Campus, Ghaziabad-201204, India
https://orcid.org/0000-0002-6651-6371

Corresponding Author(s) : Rajasekhar Komarla Kumarachari

komarla.research@gmail.com

Asian Journal of Chemistry, Vol. 36 No. 2 (2024): Vol 36 Issue 2, 2024

Abstract

In present study, six novel 2-aryl-4H-[1,3]-thiazolo[4,5-b]indoles (4a-f) were synthesized by integrating thiazole and indole motifs through a three-component one-pot condensation involving isatin, ammonium thiocyanate and arylaldehydes. Structural confirmation  was achieved using IR, 1H NMR and mass spectrometric techniques. Molecular targets, bioactivity scores, drug-likeness, anti- tuberculosis and antibacterial properties and toxicity were all predicted using various computational techniques. To calculate binding  affinities to Mycobacterium tuberculosis enoyl-ACP reductase and Escherichia coli Topoisomerase IV, in vitro bioactivity studies were  performed and Schrödinger docking simulations were performed. Anti-tubercular efficacy was evaluated using the MABA method,  while antibacterial effectiveness against both Gram-positive and Gram-negative bacteria was assessed through the agar plate method.  The results highlight the potential of these heterocyclic molecular hybrids, positioning them as promising candidates for further lead  optimization in the development of more potent and safer pharmaceutical agents. 

Keywords

Thiazolo[4,5-b]indoles Toxicity Antimicrobial activity Molecular docking
Bhargavi Posinasetty, Kumarachari , R. K., Chitrapu , P., Devineni , J., Dharmalingam , S., Naresh Babu, C., & Kumar , J. (2024). Synthesis, Antimicrobial Activity and Molecular Docking of Some Novel 2-Aryl-4H-[1,3]-thiazolo[4,5-b]indoles. Asian Journal of Chemistry, 36(2), 384–392. https://doi.org/10.14233/ajchem.2024.30986
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References
  1. G. Bérubé, Expert Opin. Drug Discov., 11, 281 (2016); https://doi.org/10.1517/17460441.2016.1135125
  2. S. Short, S. Rhodes, V. Bhave, R. Hojo and M. Jha, Synthesis, 51, 4263 (2019); https://doi.org/10.1055/s-0039-1690680
  3. A. Petrou, M. Fesatidou and A. Geronikaki, Molecules, 26, 3166 (2021); https://doi.org/10.3390/molecules26113166
  4. W.M. Eldehna, M.A. El Hassab, M.F. Abo-Ashour, T. Al-Warhi, M.M. Elaasser, N.A. Safwat, H. Suliman, M.F. Ahmed, S.T. Al-Rashood, H.A. Abdel-Aziz and R. El-Haggar, Bioorg. Chem., 110, 104748 (2021); https://doi.org/10.1016/j.bioorg.2021.104748
  5. F. Sachse and C. Schneider, Adv. Synth. Catal., 364, 77 (2022); https://doi.org/10.1002/adsc.202101168
  6. M. Konus, D. Çetin, N.D. Kizilkan, C. Yilmaz, C. Fidan, M. Algso, E. Kavak, A. Kivrak, A. Kurt-Kizildogan, Ç. Otur, D. Mutlu, A.H. Abdelsalam and S. Arslan, J. Mol. Struct., 1263, 133168 (2022); https://doi.org/10.1016/j.molstruc.2022.133168
  7. D. Lopatik, Z. Kuvaeva, O. Bondareva, V. Naidenov and L. Tychinskaya, Proc. Natl. Acad. Sci. Belarus, Chemical Ser., 55. 436 (2019); https://doi.org/10.29235/1561-8331-2019-55-4-436-441
  8. M. Ubeid, H. Thabet and S. El-Feky, Heterocycl. Commun., 22, 43 (2016); https://doi.org/10.1515/hc-2015-0135
  9. S.-i. Hattori, N. Higashi-Kuwata, H. Hayashi, S.R. Allu, J. Raghavaiah, H. Bulut, D. Das, B.J. Anson, E.K. Lendy, Y. Takamatsu, N. Takamune, N. Kishimoto, K. Murayama, K. Hasegawa, M. Li, D.A. Davis, E.N. Kodama, R. Yarchoan, A. Wlodawer, S. Misumi, A.D. Mesecar, A.K. Ghosh and H. Mitsuya, Nat. Commun., 12, 668 ( 2021); https://doi.org/10.1038/s41467-021-20900-6
  10. S. Nasri, M. Bayat, H.V. Farahani and S. Karami, Heliyon, 6, e03687 (2020); https://doi.org/10.1016/j.heliyon.2020.e03687
  11. D.G. Kim and A.V. Zhuravlyova, Chem. Heterocycl. Compd., 45, 1281 (2009); https://doi.org/10.1007/s10593-010-0421-5
  12. V.V. Marysheva and P.D. Shabanov, Bull. Exp. Biol. Med., 147, 55 (2009); https://doi.org/10.1007/s10517-009-0450-1
  13. S. Sharma, B.M. Sahoo and B.K. Banik, Lett. Org. Chem., 20, 1016 (2023); https://doi.org/10.2174/1570178620666230518145740
  14. The TB/COVID-19 Global Study Group, Eur. Respir. J., 59, 2102538 (2022); https://doi.org/10.1183/13993003.02538-2021
  15. R. Mangali and S. Muthusamy, Asian J. Org. Chem., 12, e202300142 (2023); https://doi.org/10.1002/ajoc.202300142
  16. S. Thakur, R. Sharma, R. Yadav and S. Sardana, Chem. Proc., 12, 36 (2022); https://doi.org/10.3390/ecsoc-26-13673
  17. S. Kumar and Ritika, Future J. Pharm. Sci., 6, 121 (2020); https://doi.org/10.1186/s43094-020-00141-y
  18. B.F. Abdel-Wahab and H.A. Mohamed, Phosphorus Sulfur Silicon Rel. Elem., 191, 1199 (2016); https://doi.org/10.1080/10426507.2016.1160242
  19. N.R. Candeias, L.C. Branco, P.M.P. Gois, C.A.M. Afonso and A.F. Trindade, Chem. Rev., 109, 2703 (2009); https://doi.org/10.1021/cr800462w
  20. D.A. Filimonov, A.A. Lagunin, T.A. Gloriozova, A.V. Rudik, D.S. Druzhilovskii, P.V. Pogodin and V.V. Poroikov, Chem. Heterocycl. Compd., 50, 444 (2014); https://doi.org/10.1007/s10593-014-1496-1
  21. A. Ayar, M. Aksahin, S. Mesci, B. Yazgan, M. Gül and T. Yildirim, Curr. Computeraided Drug Des., 18, 52 (2022); https://doi.org/10.2174/1573409917666210223105722
  22. T. Sander, Actelion’s Property Explorer, Allschwil, Switzerland: Actelion’s Pharmaceuticals Ltd. (2001).
  23. A. Daina, O. Michielin and V. Zoete, Sci. Rep., 7, 42717 (2017); https://doi.org/10.1038/srep42717
  24. R.A. Friesner, R.B. Murphy, M.P. Repasky, L.L. Frye, J.R. Greenwood, T.A. Halgren, P.C. Sanschagrin and D.T. Mainz, J. Med. Chem., 49, 6177 (2006); https://doi.org/10.1021/jm051256o
  25. D. Eisenberg, R. Luthy and J.U. Bowie, Methods Enzymol., 277, 396 (1997); https://doi.org/10.1016/S0076-6879(97)77022-8
  26. C. Colovos and T.O. Yeates, Protein Sci., 2, 1511 (1993); https://doi.org/10.1002/pro.5560020916
  27. S. Analysis and V. Server (2011); Available from: http://nihserver. mbi.ucla.edu/SAVES/.
  28. S.C. Lovell, I.W. Davis, W.B. Arendall 3rd, P.I. de Bakker, J.M. Word,
  29. M.G. Prisant, J.S. Richardson and D.C. Richardson, Proteins, 50, 437
  30. (2003); https://doi.org/10.1002/prot.10286
  31. Chem DrawUltra version 8.0.3 for Windows, Cambridge Soft Corporation, A subsidiary of Perkin-Elmer, Inc. (2014); Available from: www.cambridgesoft.com.
  32. https://sourceforge.net/projects/openbabel/files/openbabel/2.4.0/. License: GNU GPL v2.
  33. N.M. O’Boyle, M. Banck, C.A. James, C. Morley, T. Vandermeersch and G.R. Hutchison, J. Cheminform., 3, 33 (2011); https://doi.org/10.1186/1758-2946-3-33
  34. E. Harder, W. Damm, J. Maple, C. Wu, M. Reboul, J.Y. Xiang, L. Wang, D. Lupyan, M.K. Dahlgren, J.L. Knight, J.W. Kaus, D.S. Cerutti, G. Krilov, W.L. Jorgensen, R. Abel and R.A. Friesner, J. Chem. Theory Comput., 12, 281 (2016); https://doi.org/10.1021/acs.jctc.5b00864
  35. S.G. Franzblau, R.S. Witzig, J.C. McLaughlin, P. Torres, G. Madico, A. Hernandez, M.T. Degnan, M.B. Cook, V.K. Quenzer, R.M. Ferguson and R.H. Gilman, J. Clin. Microbiol., 36, 362 (1998); https://doi.org/10.1128/JCM.36.2.362-366.1998
  36. B. Aneja, M. Azam, S. Alam, A. Perwez, R. Maguire, U. Yadava, K. Kavanagh, C.G. Daniliuc, M.M.A. Rizvi, Q.M.R. Haq and M. Abid, ACS Omega, 3, 6912 (2018); https://doi.org/10.1021/acsomega.8b00582
  37. CLSI, M100 Performance Standards for Antimicrobial Susceptibility Testing, CLSI: Wayne, PA, USA, Edn. 29 (2019)
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