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

Copyright (c) 2024 Rajat Patel, Puja Sharma, Rohit R. Koshti, Akshay Vyas, Chetan B. Sangani

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Synthesis, Characterization, DFT Studies, Biological Investigation and Molecular Modelling of Novel 1-(5-(1H-imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)- 3-amino-2-cyano-N-phenyl-1H-benzo[f]chromene-5-carboxamide Derivatives

https://doi.org/10.14233/ajchem.2024.30936
Rajat Patel
Shri Maneklal M. Patel Institute of Sciences & Research, Kadi Sarva Vishwavidyalaya, Gandhinagar-382024, India
https://orcid.org/0000-0002-5837-6356
Puja Sharma
Shri Maneklal M. Patel Institute of Sciences & Research, Kadi Sarva Vishwavidyalaya, Gandhinagar-382024, India
https://orcid.org/0000-0002-0896-8281
Rohit R. Koshti
Shri Maneklal M. Patel Institute of Sciences & Research, Kadi Sarva Vishwavidyalaya, Gandhinagar-382024, India
https://orcid.org/0000-0002-3144-9543
Akshay Vyas
Shri Maneklal M. Patel Institute of Sciences & Research, Kadi Sarva Vishwavidyalaya, Gandhinagar-382024, India
https://orcid.org/0000-0002-7715-2796
Chetan B. Sangani
Department of Chemistry, Government Science College, Sector-15, Gandhinagar-382016, India
https://orcid.org/0000-0001-6028-8833

Corresponding Author(s) : Chetan B. Sangani

chetansangani1986@yahoo.com

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

Abstract

In this work, a new series of imidazole-pyrazole-benzo[f]chromene hybrids were designed and synthesized by a base-catalyzed cyclo-condensation through a one-pot multicomponent reaction. All compounds were tested for in vitro antimicrobial and anticancer activities. Enzyme inhibitory activities of all compounds were carried out against FabH and EGFR. The majority of synthesized  compounds displayed promising antimicrobial as well as anticancer activity against used strains and cancer cell lines respectively. The  compounds were also tested for in vitro anticancer activities against two cancer cell lines A549 and Hep G2. Compound 7f (IC50 = 0.62  µM) against EGFR and (IC50 = 1.31 µM) against A549 kinase displayed the most potent inhibitory activity as compared to another  member of the series. In the molecular modelling study, compound 7e was bound into the active pocket of EGFR with one pi-pi  interaction and one hydrogen bond having minimum binding energy ∆Gb = −7.6894 kcal/mol. Moreover, FabH molecule 7d was found  to be binding in the active pocket with a minimum binding energy of −8.9117 kcal/mol. 

Keywords

anticancer activity , imidazole-pyrazole-benzo[f]chromene hybrid Enzyme inhibitory activity molecular modeling one pot multicomponent
Patel, R., Sharma, P., Koshti, R. R., Vyas, A., & Sangani, C. B. (2024). Synthesis, Characterization, DFT Studies, Biological Investigation and Molecular Modelling of Novel 1-(5-(1H-imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)- 3-amino-2-cyano-N-phenyl-1H-benzo[f]chromene-5-carboxamide Derivatives. Asian Journal of Chemistry, 36(2), 361–370. https://doi.org/10.14233/ajchem.2024.30936
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References
  1. T. S. Ibrahim, M. M. Hawwas , E. Taher , N. A. Alhakamy, M A. Alfaleh , M.Elagawany , Bahaa Elgendy, Gamal M. Zayed, Mamdouh F.A. Mohamed , Zakaria K. Abdel-Samii , Y. A.M.M. Elshaier, Bioorganic Chemistry , 105, 104352 (2020)
  2. R.L. Siegel, K.D. Miller, H.E. Fuchs and A. Jemal, CA Cancer J. Clin., 71, 7 (2021); https://doi.org/10.3322/caac.21654
  3. M. Morales-Cruz, Y. Delgado, B Castillo, C. M Figueroa, A. M Molina, A. Torres, M. Milián, K. Griebenow, Drug Design, Development and Therapy, 13 3753–3772 (2019)
  4. . M. Tateishi and T. Ishida, Cancer Res., 50, 7077 (1990).
  5. A. Ayati, et al. Bioorganic Chemistry 99 (2020) 103811 https://doi.org/10.1016/j.bioorg.2020.103811
  6. . S.W. White, J. Zheng, Y.M. Zhang and C.O. Rock, Annu. Rev. Biochem., 74, 791 (2005); https://doi.org/10.1146/annurev.biochem.74.082803.133524
  7. . K.S. Kolibaba and B.J. Druker, Biochim. Biophys. Acta, 1333, F217 (1997);
  8. . Meuillet/Bremer, Pediatr Neurosurg 1998;29:1–13
  9. . Sequist, The Oncologist 2007;12:325–330
  10. M.C. Mandewale et al. / Beni-Suef Univ. J. Basic Appl. Sci. 6 (2017) 354–361
  11. Xiang Wen • Shi-Ben Wang • Da-Chuan Liu • Guo-Hua Gong • Zhe-Shan Quan , Med Chem Res DOI 10.1007/s00044-015-1323-y
  12. R. Kaur and K. Kumar, European Journal of Medicinal Chemistry 215 (2021) 113220
  13. Zhang, F.; et al. Bioorg. Med. Chem. Lett. (2013), http://dx.doi.org/10.1016/j.bmcl.2013.11.079 [14] White et al Annu. Rev. Biochem. 2005. 74:791–831 doi:10.1146/annurev.biochem.74.082803.133524
  14. Ying-Jie Lu, Yong-Mei Zhang, and Charles O. Rock, Biochem. Cell Biol. 82: 145–155 (2004) doi: 10.1139/O03-076
  15. Ming Chen* and Jiaoti Huang*, Precision Clinical Medicine, 2(3), 2019, 183–191 doi: 10.1093/pcmedi/pbz017
  16. Y.-T. Wang, T.-Q. Shi, J. Fu, H.-L. Zhu, European Journal of Medicinal Chemistry (2019), doi: https:// doi.org/10.1016/j.ejmech.2019.03.026.
  17. K.S. Gajiwala et al. / FEBS Letters 583 (2009) 2939–2946 doi:10.1016/j.febslet.2009.08.001
  18. M. Negi, P.A. Chawla, A. Faruk, V. Chawla, Bioorganic Chemistry (2020), doi: https://doi.org/10.1016/j.bioorg.2020.104315
  19. A. Mermer et al., Bioorganic Chemistry 114 (2021) 105076 https://doi.org/10.1016/j.bioorg.2021.105076
  20. P. Yadav and K. Shah Bioorganic Chemistry 109 (2021) 104639 https://doi.org/10.1016/j.bioorg.2021.104639
  21. J. Drogosz-Stachowicz, et al Chemico-Biological Interactions 320 (2020) 109005 https://doi.org/10.1016/j.cbi.2020.109005
  22. K.D. Katariya, S.R. Shah, D. Reddy, Bioorganic Chemistry (2019), doi: https://doi.org/10.1016/j.bioorg.2019.103406
  23. Robert Musiol, Expert Opinion on Drug Discovery, DOI: 10.1080/17460441.2017.1319357
  24. M.C. Mandewale etal., Beni-Suef Univ. J. Basic Appl. Sci. 6 (2017) 354–361 http://dx.doi.org/10.1016/j.bjbas.2017.07.005
  25. Teng, P., Li, C., Peng, Z., Marie Vanderschouw, A., Nimmagadda, A., Su, M., Li, Y., Sun, X., Cai, J., Bioorganic & Medicinal Chemistry (2018), doi: https://doi.org/10.1016/j.bmc.2018.05.031
  26. Xiao Z, Lei F, Chen X, et al. Arch Pharm Chem Life Sci. 2018;1–11 DOI: 10.1002/ardp.201700407
  27. D. Mantu et al. J Enzyme Inhib Med Chem, Early Online: 1–8
  28. DOI: 10.1080/14756366.2016.1190711
  29. A. Irfan et al. Journal of Enzyme Inhibition and Medicinal Chemistry 2020, VOL. 35, NO. 1, 265–279 https://doi.org/10.1080/14756366.2019.1698036
  30. Haroun et al. Current Topics in Medicinal Chemistry, 2018, Vol. 18, No. 1
  31. DOI: 10.2174/1568026618666180206101814
  32. N. C. Desai, D. Pandya, D. Vaja, Med Chem Res DOI 10.1007/s00044-017-2040-5
  33. Singh et al., International Current Pharmaceutical Journal 2012, 1(5): 119-127 http://www.icpjonline.com/documents/Vol1Issue5/05.pdf
  34. Ruhi Ali and Nadeem Siddiqui Journal of Chemistry Volume 2013, Article ID 345198, http://dx.doi.org/10.1155/2013/345198
  35. R Kurtaran, S Odabaşıoğlu, A Azizoglu, H Kara, O Atakol, Polyhedron, 26, 5069,
  36. (2007).
  37. Mahmoud WH, Omar MM, Sayed FN, Mohamed GG. Synthesis, characterization,
  38. spectroscopic and theoratical studies of transition metal complexes of new nano Schiff base
  39. derived from L-histidine and 2-acetylferrocene and evaluation of biological and anticancer
  40. activities. Appl. Organomet. Chem 32(7):4386-4390. (2018).
  41. Neese, F. The ORCA program system, Wiley Interdiscip. Rev.: Comput. Mol. Sci., 2012;2, 73–78.
  42. Neese, F. Software update: the ORCA program system, version 4.0, Wiley Interdiscip. Rev.: Comput. Mol. Sci.2017; 8, e1327.
  43. P Sharma, R Patel, RR Koshti, A Vyas, & CB Sangani. Synthesis, Biological Evaluation and Molecular Modeling of Pyrazole-Phthalazine Hybrid Derivatives Bearing 2-Aryloxy Quinoline Nucleus and their Computational Quantum Mechanical Modelling. Asian Journal of Chemistry, 34(12), 3169-3182. (2022).
  44. R Patel, P Sharma, RR Koshti, A Vyas, & CB Sangani. Synthesis, Characterization and molecular modeling of pyrazole-quinoline hybrids as a new class of antibacterial, antimicrobial, anticancer agents and DFT study. Asian Journal of Chemistry, 35(4), 828-838. (2023).
  45. P Sharma, R Patel, RR Koshti, A Vyas, & CB Sangani. Synthesis, Synthesis, Biological Evaluation and Molecular Modeling of Novel Ethyl 2′-Amino-5′-oxo-1′-(4-phenylthiazol-2-yl)-2-(phenylthio)-1′,4′,5′,6′,7′,8′-hexahydro-[3,4′-biquinoline]-3′-carboxylate Derivatives and their Computational Quantum Mechanical Modelling. Asian Journal of Chemistry, 35(6), 1320-1332. (2023).
  46. R Patel, P Sharma, RR Koshti, A Vyas, & CB Sangani. Synthesis, Synthesis, Biological Evaluation, DFT Studies and Molecular Docking of Novel 4-(5-(1H-Imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-amino-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile and its Derivatives. Asian Journal of Chemistry, 35(7):1616-1624. (2023).
  47. P Sharma, R Patel, RR Koshti, A Vyas, & CB Sangani. Synthesis, Characterization, Biological Evaluation, DFT Studies and Molecular Docking of Novel 12-(2-(1H-Imidazol-1-yl)quinolin-3-yl)-8-methyl-2,3,4,12-tetrahydro-1H-benzo[4,5]thiazolo[2,3-b]quinazolin-1-one and its Derivatives. Asian Journal of Chemistry, 35(9):2092-2102. (2023).
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