Copyright (c) 2024 Nagaraju Myakala, Kotaiah Kandula, Nagamani Rayala, Sateesh Kuna, Vishnu Thumma, A.K.D. Bhavani
This work is licensed under a Creative Commons Attribution 4.0 International License.
Design and Synthesis of Novel Quinazolin-4(3H)-One Appended 1,2,4-Oxadiazoles as Antimicrobial Agents
Corresponding Author(s) : A.K.D. Bhavani
Asian Journal of Chemistry,
Vol. 36 No. 8 (2024): Vol 36 Issue 8, 2024
Abstract
A novel series of hybrid heterocycles having quinazolinone based 1,2,4-oxadiazoles scaffold with methylamino linkage were obtained in two synthetic pathways. In method I, quinazolinone based ester reacted with amidoximes and gave the corresponding hybrid products in poor yields. To reduce the duration of reaction time and increase the yields of the products, dehydrochlorination reaction of 6-aminoquinazolinone was carried out with 5-chloromethyl-1,2,4-oxadiazoles in other synthetic method, which furnished the products in good to excellent yields. The synthesized 1,2,4-oxadiazole hybrids were characterized using spectroscopic techniques and also screened for their antimicrobial activity against bacteria and fungi, among which chloro-substituted analogues 6d and 6e presented potent activity against all strains whereas other analogues proven to have moderate activities.
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- T.M. Dhameliya, S.S. Chourasiya, E. Mishra, P.S. Jadhavar, P.V. Bharatam and A.K. Chakraborti, J. Org. Chem., 82, 10077 (2017); https://doi.org/10.1021/acs.joc.7b01548
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- Y. Ergün, Ö.F. Orhan, U.G. Özer and G. Gisi, Eur. J. Pharmacol., 630, 74 (2010); https://doi.org/10.1016/j.ejphar.2009.12.021
- D. Kumar, G. Patel, A.K. Chavers, K.-H. Chang and K. Shah, Eur. J. Med. Chem., 46, 3085 (2011); https://doi.org/10.1016/j.ejmech.2011.03.031
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- H. Kashtoh, S. Hussain, A. Khan, S.M. Saad, J.A.J. Khan, K.M. Khan, S. Perveen and M.I. Choudhary, Bioorg. Med. Chem., 22, 5454 (2014); https://doi.org/10.1016/j.bmc.2014.07.032
- P.C. Unangst, G.P. Shrum, D.T. Connor, R.D. Dyer and D.J. Schrier, J. Med. Chem., 35, 3691 (1992); https://doi.org/10.1021/jm00098a015
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- S.A. Shendy, M. Babazadeh, G.H. Shahverdizadeh, R. Hosseinzadeh-Khanmiri, and M. Es'haghi, Mol. Divers., 25, 889 (2021); https://doi.org/10.1007/s11030-020-10033-1
- H. Cassebaum, J. Prakt. Chem., 23, 301 (1964); https://doi.org/10.1002/prac.19640230509
- S.S. Kulkarni, S. Singh, J.R. Shah, W.-K. Low, and T. T. Talele, Eur. J. Med. Chem., 50, 264 (2012); https://doi.org/10.1016/j.ejmech.2012.02.001
- Y. Dürüst, H. Karaku, M. Kaiser and D. Tasdemir, Eur. J. Med. Chem., 48, 296 (2012); https://doi.org/10.1016/j.ejmech.2011.12.028
- C. Erhonyota, G.I. Edo, and F.O. Onoharigho, Acta Ecol. Sin., 43, 684 (2023); https://doi.org/10.1016/j.chnaes.2022.08.006
References
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J.-J. Wang, W. Sun, W.-D. Jia, M. Bian, and L.-J. Yu, J. Enzyme Inhib. Med. Chem., 37, 2304 (2022); https://doi.org/10.1080/14756366.2022.2115036
Y.A. Al-Soud, M. N. Al-Dweri and N. A. Al-Masoudi, Il Farmaco, 59, 775 (2004); https://doi.org/10.1016/j.farmac.2004.05.006
Y. Ergün, Ö.F. Orhan, U.G. Özer and G. Gisi, Eur. J. Pharmacol., 630, 74 (2010); https://doi.org/10.1016/j.ejphar.2009.12.021
D. Kumar, G. Patel, A.K. Chavers, K.-H. Chang and K. Shah, Eur. J. Med. Chem., 46, 3085 (2011); https://doi.org/10.1016/j.ejmech.2011.03.031
M. Gobec, T. Tomašic, T. Markovic, I. Mlinaric-Rašcan, M.S. Dolenc, and Ž. Jakopin, Chem.-Biol. Interact., 240, 200 (2015); https://doi.org/10.1016/j.cbi.2015.08.018
G. Chawla, Mini-Rev. Med. Chem., 18, 1536 (2018); https://doi.org/10.2174/1389557518666180524112050
P. Pitasse-Santos, V. Sueth-Santiago and M. Lima, J. Braz. Chem. Soc., 29, 435 (2018); https://doi.org/10.21577/0103-5053.20170208
B. B.Ceyhan and S. Karakurt, Respir. Med., 96, 61 (2002); https://doi.org/10.1053/rmed.2001.1199
I.M. Coupar, A. Hedges, H.L. Metcalfe and P. Turner, J. Pharm. Pharmacol., 21, 474 (2011); https://doi.org/10.1111/j.2042-7158.1969.tb08294.x
H.A. Rotbart and A.D. Webster, Clin. Infect. Dis., 32, 228 (2001); https://doi.org/10.1086/318452
S. Huang, A. Bhattacharya, M.D. Ghelfi, C. Fritsch, D.M. Chenoweth, H. Li, Y.E. Goldman and B.S. Cooperman, Nat. Commun., 13, 2413 (2022); https://doi.org/10.1038/s41467-022-30080-6
B. Catanese, R. Lisciani, and B. Silvestrini, Pharmacol. Res. Commun., 2, 83 (1970); https://doi.org/10.1016/S0031-6989(70)80013-3
H. Kashtoh, S. Hussain, A. Khan, S.M. Saad, J.A.J. Khan, K.M. Khan, S. Perveen and M.I. Choudhary, Bioorg. Med. Chem., 22, 5454 (2014); https://doi.org/10.1016/j.bmc.2014.07.032
P.C. Unangst, G.P. Shrum, D.T. Connor, R.D. Dyer and D.J. Schrier, J. Med. Chem., 35, 3691 (1992); https://doi.org/10.1021/jm00098a015
N. Myakala, K. Kandula, N. Rayala, S. Kuna, V. Thumma and K.D.B. Anagani, Chem. Biodivers., 20, e202300800 (2023); https://doi.org/10.1002/cbdv.202300800
M.K. Vanga, R. Bhukya, V. Thumma, S.S.S.S.S. Ambadipudi, V.L. Nayak, S.B. Andugulapati and V. Manga, RSC Med. Chem., 15, 1709 (2024); https://doi.org/10.1039/D4MD00015C
S.A. Shendy, M. Babazadeh, G.H. Shahverdizadeh, R. Hosseinzadeh-Khanmiri, and M. Es'haghi, Mol. Divers., 25, 889 (2021); https://doi.org/10.1007/s11030-020-10033-1
H. Cassebaum, J. Prakt. Chem., 23, 301 (1964); https://doi.org/10.1002/prac.19640230509
S.S. Kulkarni, S. Singh, J.R. Shah, W.-K. Low, and T. T. Talele, Eur. J. Med. Chem., 50, 264 (2012); https://doi.org/10.1016/j.ejmech.2012.02.001
Y. Dürüst, H. Karaku, M. Kaiser and D. Tasdemir, Eur. J. Med. Chem., 48, 296 (2012); https://doi.org/10.1016/j.ejmech.2011.12.028
C. Erhonyota, G.I. Edo, and F.O. Onoharigho, Acta Ecol. Sin., 43, 684 (2023); https://doi.org/10.1016/j.chnaes.2022.08.006