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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
Corresponding Author(s) : Chetan B. Sangani
Asian Journal of Chemistry,
Vol. 35 No. 7 (2023): Vol 35 Issue 7 (2023)
Abstract
A novel series consisting of eight imidazol-pyrazole hybrids (9a-h) are synthesized using a base catalyzed one pot multi-component reaction (MCR) and screened for in vitro biological activities. All compounds were found to display high biological activities but compound 9g was found to be the most active against EGFR (IC50 of 0.11 ± 0.02 μm), A549 and HepG2, while compound 9h was found to be most active against FabH (IC50 of 2.6 μm) E. coli. The DFT studies and molecular docking was done for compounds 9a-h to calculate the distance and angle between the active parts of the molecules and charge density over the molecules affecting the binding of molecules in the active pockets with greater binding affinity.
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- S. Thakral and V. Singh, Curr. Bioact. Compd., 15, 316 (2019); https://doi.org/10.2174/1573407214666180614121140
- J.J. Malin and E. de Leeuw, Infect. Drug Resist., 12, 2613 (2019); https://doi.org/10.2147/IDR.S215070
- D.R. Giacobbe, M. Mikulska and C. Viscoli, Expert Rev. Clin. Pharmacol., 11, 1219 (2018); https://doi.org/10.1080/17512433.2018.1549487
- J. Jampilek, Molecules, 24, 3839 (2019); https://doi.org/10.3390/molecules24213839
- M. Henary, C. Kananda, L. Rotolo, B. Savino, E.A. Owens and G. Cravotto, RSC Adv., 10, 14170 (2020); https://doi.org/10.1039/D0RA01378A
- N. Kerru, L. Gummidi, S. Maddila, K.K. Gangu and S.B. Jonnalagadda, Molecules, 25, 1909 (2020); https://doi.org/10.3390/molecules25081909
- M. Ramadan, A.A. Aly, L.E.A. El-Haleem, M.B. Alshammari and S. Bräse, Molecules, 26, 4995 (2021); https://doi.org/10.3390/molecules26164995
- K. Tabassum, P. Ekta and P. Kavitkumar, Mini-Rev. Org. Chem., 15, 459 (2018); https://doi.org/10.2174/1570193X15666171211170100
- A. Balbi, M. Anzaldi, C. Macciò, C. Aiello, M. Mazzei, R. Gangemi, P. Castagnola, M. Miele, C. Rosano and M. Viale, Eur. J. Med. Chem., 46, 5293 (2011); https://doi.org/10.1016/j.ejmech.2011.08.014
- K. Karrouchi, S. Radi, Y. Ramli, J. Taoufik, Y. Mabkhot, F. Al-aizari and M. Ansar, Molecules, 23, 134 (2018); https://doi.org/10.3390/molecules23010134
- M. Mantzanidou, E. Pontiki and D. Hadjipavlou-Litina, Molecules, 26, 3439 (2021); https://doi.org/10.3390/molecules26113439
- D.S. Zinad, A. Mahal and O.A. Shareef, IOP Conf. Ser.: Mater. Sci. Eng., 770, 012053 (2020); https://doi.org/10.1088/1757-899X/770/1/012053
- H.A. Abd El Razik, M.H. Badr, A.H. Atta, S.M. Mouneir and M.M. Abu-Serie, Arch. Pharm., 350, e1700026 (2017); https://doi.org/10.1002/ardp.201700026
- C.B. Sangani, J.A. Makawana, Y.-T. Duan, Y. Yin, S.B. Teraiya, N.J. Thumar and H.-L. Zhu, Bioorg. Med. Chem. Lett., 24, 4472 (2014); https://doi.org/10.1016/j.bmcl.2014.07.094
- J.A. Makawana, C.B. Sangani, L. Lin and H.-L. Zhu, Bioorg. Med. Chem. Lett., 24, 1734 (2014); https://doi.org/10.1016/j.bmcl.2014.02.041
- C.B. Sangani, J.A. Makawana, X. Zhang, S.B. Teraiya, L. Lin and H.-L. Zhu, Bioorg. Med. Chem. Lett., 76, 549 (2014); https://doi.org/10.1016/j.ejmech.2014.01.018
- C.B. Sangani, H.H. Jardosh, M.P. Patel and R.G. Patel, Med. Chem. Res., 22, 3035 (2013); https://doi.org/10.1007/s00044-012-0322-5
- I. Ali, M.N. Lone and H.Y. Aboul-Enein, MedChemComm, 8, 1742 (2017); https://doi.org/10.1039/C7MD00067G
- F. Neese, Wiley Interdiscip. Rev. Comput. Mol. Sci., 8, e1327 (2017); https://doi.org/10.1002/wcms.1327
- R. Kurtaran, S. Odabasioglu, A. Azizoglu, H. Kara and O. Atakol, Polyhedron, 26, 5069 (2007); https://doi.org/10.1016/j.poly.2007.07.021
- W.H. Mahmoud, M.M. Omar, F.N. Sayed and G.G. Mohamed, Appl. Organomet. Chem., 32, 4386 (2018); https://doi.org/10.1002/aoc.4386
- P. Sharma, R. Patel, R.R. Koshti, A. Vyas and C.B. Sangani, Asian J. Chem., 34, 3169 (2022); https://doi.org/10.14233/ajchem.2022.23981
References
S. Thakral and V. Singh, Curr. Bioact. Compd., 15, 316 (2019); https://doi.org/10.2174/1573407214666180614121140
J.J. Malin and E. de Leeuw, Infect. Drug Resist., 12, 2613 (2019); https://doi.org/10.2147/IDR.S215070
D.R. Giacobbe, M. Mikulska and C. Viscoli, Expert Rev. Clin. Pharmacol., 11, 1219 (2018); https://doi.org/10.1080/17512433.2018.1549487
J. Jampilek, Molecules, 24, 3839 (2019); https://doi.org/10.3390/molecules24213839
M. Henary, C. Kananda, L. Rotolo, B. Savino, E.A. Owens and G. Cravotto, RSC Adv., 10, 14170 (2020); https://doi.org/10.1039/D0RA01378A
N. Kerru, L. Gummidi, S. Maddila, K.K. Gangu and S.B. Jonnalagadda, Molecules, 25, 1909 (2020); https://doi.org/10.3390/molecules25081909
M. Ramadan, A.A. Aly, L.E.A. El-Haleem, M.B. Alshammari and S. Bräse, Molecules, 26, 4995 (2021); https://doi.org/10.3390/molecules26164995
K. Tabassum, P. Ekta and P. Kavitkumar, Mini-Rev. Org. Chem., 15, 459 (2018); https://doi.org/10.2174/1570193X15666171211170100
A. Balbi, M. Anzaldi, C. Macciò, C. Aiello, M. Mazzei, R. Gangemi, P. Castagnola, M. Miele, C. Rosano and M. Viale, Eur. J. Med. Chem., 46, 5293 (2011); https://doi.org/10.1016/j.ejmech.2011.08.014
K. Karrouchi, S. Radi, Y. Ramli, J. Taoufik, Y. Mabkhot, F. Al-aizari and M. Ansar, Molecules, 23, 134 (2018); https://doi.org/10.3390/molecules23010134
M. Mantzanidou, E. Pontiki and D. Hadjipavlou-Litina, Molecules, 26, 3439 (2021); https://doi.org/10.3390/molecules26113439
D.S. Zinad, A. Mahal and O.A. Shareef, IOP Conf. Ser.: Mater. Sci. Eng., 770, 012053 (2020); https://doi.org/10.1088/1757-899X/770/1/012053
H.A. Abd El Razik, M.H. Badr, A.H. Atta, S.M. Mouneir and M.M. Abu-Serie, Arch. Pharm., 350, e1700026 (2017); https://doi.org/10.1002/ardp.201700026
C.B. Sangani, J.A. Makawana, Y.-T. Duan, Y. Yin, S.B. Teraiya, N.J. Thumar and H.-L. Zhu, Bioorg. Med. Chem. Lett., 24, 4472 (2014); https://doi.org/10.1016/j.bmcl.2014.07.094
J.A. Makawana, C.B. Sangani, L. Lin and H.-L. Zhu, Bioorg. Med. Chem. Lett., 24, 1734 (2014); https://doi.org/10.1016/j.bmcl.2014.02.041
C.B. Sangani, J.A. Makawana, X. Zhang, S.B. Teraiya, L. Lin and H.-L. Zhu, Bioorg. Med. Chem. Lett., 76, 549 (2014); https://doi.org/10.1016/j.ejmech.2014.01.018
C.B. Sangani, H.H. Jardosh, M.P. Patel and R.G. Patel, Med. Chem. Res., 22, 3035 (2013); https://doi.org/10.1007/s00044-012-0322-5
I. Ali, M.N. Lone and H.Y. Aboul-Enein, MedChemComm, 8, 1742 (2017); https://doi.org/10.1039/C7MD00067G
F. Neese, Wiley Interdiscip. Rev. Comput. Mol. Sci., 8, e1327 (2017); https://doi.org/10.1002/wcms.1327
R. Kurtaran, S. Odabasioglu, A. Azizoglu, H. Kara and O. Atakol, Polyhedron, 26, 5069 (2007); https://doi.org/10.1016/j.poly.2007.07.021
W.H. Mahmoud, M.M. Omar, F.N. Sayed and G.G. Mohamed, Appl. Organomet. Chem., 32, 4386 (2018); https://doi.org/10.1002/aoc.4386
P. Sharma, R. Patel, R.R. Koshti, A. Vyas and C.B. Sangani, Asian J. Chem., 34, 3169 (2022); https://doi.org/10.14233/ajchem.2022.23981