Copyright (c) 2024 Ganesh Sonawane, Shweta Sharma, Ritu Gilhotra
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and Pharmacological Screening of 1,3,4-Oxadiazoles
Corresponding Author(s) : Ganesh Sonawane
Asian Journal of Chemistry,
Vol. 36 No. 6 (2024): Vol 36 Issue 6, 2024
Abstract
Two series of 1,3,4-oxadiazole scaffolds (10a-j & 12a-j) were synthesized and comprehensively characterized using IR, NMR and mass spectra. Subsequently, the synthesized compounds underwent screening for anticancer activity against HepG2 and MCF-7 cell lines. All the 20 compounds exhibited substantial anticancer activity with compounds 10b and 10e demonstrating particularly significant activity surpassing that of the standard 5-fluorouracil. Significantly, compound 10b displayed superior efficacy compared to compound 10e, prompting its selection for further in vivo assessment against diethylnitrosamine-induced hepatocellular carcinoma. In in vivo evaluation, compound 10b significantly reduced levels of AST, ALT, ALP and bilirubin in comparison to the positive control group. It also exhibited significant hepatoprotective effects, albeit marginally less potent than standard 5-fluorouracil. These findings underscore the considerable potential of compound 10b as an anticancer agent within the series, suggesting its candidacy for further development and clinical exploration in cancer therapeutics.
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Y. Xia, M. Sun, H. Huang and W.-L. Jin, Signal Transduct. Target Ther., 9, 92 (2024); https://doi.org/10.1038/s41392-024-01808-1
F. Wang, D.-Y. Ruan and R.-H. Xu, Cell, 187, 1578 (2024); https://doi.org/10.1016/j.cell.2024.02.040
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M.J. Ahsan, Mini Rev. Med. Chem., 22, 164 (2022); 10.2174/1389557521666210226145837
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E.M. Goldblatt and W.H. Lee, Am. J. Transl. Res., 2, 1 (2010).
B. Victoir, C. Croix, F. Gouilleux and G. Prié, Cancers, 16, 461 (2024); https://doi.org/10.3390/cancers16020461
L. Yurttas, B.K. Çavusoglu, G.A. Çiftçi and H.E. Temel, Anticancer Agents Med. Chem., 18, 914 (2018); https://doi.org/10.2174/1871520618666180322123327
A.C. Kumar, J. Rangaswamy, Madalambika, P.M. BharathKumar, P.R. Patil, M. Salavadi and N. Naik, J. Mol. Struct., 138749 (2024); https://doi.org/10.1016/j.molstruc.2024.138749
G. Sonawane, S. Sharma and R. Gilhotra, Asian J. Chem., 36, 1072 (2024); https://doi.org/10.14233/ajchem.2024.31342
Y. Ono, M. Ninomiya, D. Kaneko, A.D. Sonawane, T. Udagawa, K. Tanaka, A. Nishina and M. Koketsu, Bioorg. Chem., 104, 104245 (2020); https://doi.org/10.1016/j.bioorg.2020.104245
M. Soleiman-Beigi, R. Aryan, M. Yousofizadeh and S. Khosravi, J. Chem. 2013, 476358 (2013); https://doi.org/10.1155/2013/476358
T. Glomb, K. Szymankiewicz and P. Swiatek, Molecules, 23, 3361 (2018); https://doi.org/10.3390/molecules23123361
D. Mukherjee and R. Ahmad, Interdiscip. Toxicol., 8, 1 (2015); https://doi.org/10.1515/intox-2015-0001
K.K. Dar, S. Ali, M. Ejaz, S. Nasreen, N. Ashraf, S.F. Gillani, N. Shafi, S. Safeer, M.A. Khan, S. Andleeb and T.A. Mughal, Braz. J. Biol., 79, 629 (2019); https://doi.org/10.1590/1519-6984.186565
S. Sundaresan and P. Subramanian, Pol. J. Pharmacol., 55, 37 (2003).
R. Kartik, C.V. Rao, P. Pushpangadan, S.P. Trivedi and G.D. Reddy, Iranian J. Pharm. Sci., 6, 99 (2010).
E.S. Mohammed, N.M. El-Beih, E.A. El-Hussieny, E. El-Ahwany, M. Hassan and M. Zoheiry, Arch. Med. Sci., 17, 218 (2021); https://doi.org/10.5114/aoms.2020.93739
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R.H. Hussein and F.K. Khalifa, Saudi J. Biol. Sci., 21, 589 (2014); https://doi.org/10.1016/j.sjbs.2014.03.004
K. Pansare, C. Upasani, A. Upaganlwar, G. Sonawane and C. Patil, Vidyabharati Int. Interdisciplinary Res. J., 320 (2021).
G.M. Safwat, K.M.A. Hassanin, E.T. Mohammed, E.K. Ahmed, M.R. Abdel Rheim, M.A. Ameen, M. Abdel-Aziz, A.M. Gouda, I. Peluso, R. Almeer, M.M. Abdel-Daim and A. Abdel-Wahab, Oxid. Med. Cell. Longev., 2021, 4759821 (2021); https://doi.org/10.1155/2021/4759821