Copyright (c) 2023 Usha Rani Peddaboina, ANITHA SADHULA, Ravinder Nath Anisetti
This work is licensed under a Creative Commons Attribution 4.0 International License.
Coumarin Imidazolone Hybrid as Inhibitor of Topoisomerase Type II and Hsp90 and as Potent Antimicrobials
Corresponding Author(s) : Ravinder Nath Anisetti
Asian Journal of Chemistry,
Vol. 35 No. 11 (2023): Vol 35 Issue 11, 2023
Abstract
In present study, coumarin imidazolone hybrids were synthesized on the basis of the molecular docking analysis of the compounds (11a-h) by using PyRx 0.8 software. The molecules docking studies were performed against the targets Hsp90 and human type IIA DNA topoisomerase and compared the same with standard drugs fluconazole and doxorubicin. Among all the compounds 11d (-12.7 kcal/mol) and 11f (-12.4 kcal/mol) showed good binding affinity towards human Hsp90 and 11d (-11.5 kcal/mol) and 11e (-11.4 kcal/mol) showed good binding affinity against human type IIA DNA topoisomerase. Based on the positive results a series of eight novel titled compounds (1-(4-(4-(arylidene)-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)phenyl)ethylidene)-2-oxo-2H-chromene-3- arbohydrazides (11a-h) have been prepared by the method of condensation of 1-(4-acetylphenyl)-4-arylidene-2-phenyl-1H-imidazol- (4H)-ones (5a-h) with 2-oxo-2H-chromene-3-carbohydrazide (10). Characterization of the synthesized compounds were conducted by FT-IR, 1H NMR, 13C NMR, mass spectral studies and screened for their antioxidant, anticancer and antimicrobial activities. The compounds were analyzed for physico-chemical and pharmacokinetic properties of all the compounds showed good to moderate properties.
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C.A. Juan, J.M.P. de la Lastra, F.J. Plou and E. Pérez-Lebeña, Int. J. Mol. Sci., 22, 4642 (2021); https://doi.org/10.3390/ijms22094642
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Z.H. Chohan and C.T. Supuran, J. Comput. Methods Mol. Des., 2, 51 (2012).
D. Lanneau, M. Brunet, E. Frisan, E. Solary, M. Fontenay and C. Garrido, J. Cell Mol. Med., 12, 743 (2008); https://doi.org/10.1111/j.1582-4934.2008.00273.x
H. Wei, A.J. Ruthenburg, S.K. Bechis and G.L. Verdine, J. Biol. Chem., 280, 37041 (2005); https://doi.org/10.1074/jbc.M506520200
B. Abdi, M. Fekadu, D. Zeleke, R. Eswaramoorthy and Y. Melaku, J. Chem., 2021, 2408006 (2021); https://doi.org/10.1155/2021/2408006
M.W. Amolins and B.S.J. Blagg, Mini Rev. Med. Chem., 9, 140 (2009); https://doi.org/10.2174/138955709787316056
B.S. Furniss, A.J. Hannaford, P.W.G. Smith and A.R. Tatchell, Vogel’s Textbook of Practical Organic Chemistry, Longman: England, edn 5 (1989).
D. Amsterdam, eds.: V. Lorian, Susceptibility Testing of Antimicrobials in Liquid Media. In: Antibiotics in Library Medicine, Williams and Wilkins: Baltimore, USA, Edn. 4 (1996)
S.E. Lee, H.J. Hwang, J.S. Ha, H.-S. Jeong and J.H. Kim, Life Sci., 73, 167 (2003); https://doi.org/10.1016/S0024-3205(03)00259-5
M. Koparir, C. Orek, A.E. Parlak, A. Söylemez, P. Koparir, M. Karatepe and S.D. Dastan, Eur. J. Med. Chem., 63, 340 (2013); https://doi.org/10.1016/j.ejmech.2013.02.025
T. Mosmann, J. Immunol. Methods, 1983, 55 (1983); https://doi.org/10.1016/0022-1759(83)90303-4
M.C. Alley, D.A. Scudiero, A. Monks, M.L. Hursey, M.J. Czerwinski, D.L. Fine, B.J. Abbott, J.G. Mayo, R.H. Shoemaker and M.R. Boyd, Cancer Res., 48, 589 (1988).
A. Wadood, M. Riaz, S.B. Jamal, M. Shah and M.A. Lodhi, Bioinformation, 9, 309 (2013); https://doi.org/10.6026/97320630009309
T.O. Johnson, A.E. Adegboyega, O. Iwaloye, O.A. Eseola, W. Plass, B. Afolabi, D. Rotimi, E.I. Ahmed, A. Albrakati, G.E. Batiha and O.S. Adeyemi, J. Pharmacol. Sci., 147, 62 (2021); https://doi.org/10.1016/j.jphs.2021.05.004