In an attempt to develop quality antimicrobial agents, a series of oxazolone-1,2,3-triazole-amide hybrids were obtained from oxazolone tethered with a terminal alkyne and in situ generated 2-azido-N-phenylacetamides. All the synthesized compounds were characterized by using various spectroscopic techniques. The developed hybrids were evaluated for their in vitro antimicrobial activity toward three Gram-positive bacteria S. aureus, B. subtilis and S. gorodonii and three Gram-negative bacteria—E. coli, S. enterica and P. aeruginosa—and two fungi, viz. C. albicans and A. niger. Oxazolone-amide-1,2,3-triazoles (8a–e, 9a–e, 10a–e) exhibited almost 15 times better efficacy than alkyne precursors, i.e., oxazolone-linked terminal alkynes (6a–c). Compound 10d exhibited very good antimicrobial activity toward all the tested microorganisms. Docking studies of compounds 10d and 6c were also carried out in the binding site of enzyme sterol-14-α-demethylase of C. albicans, which supported the in vitro experimental results.
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H.D. Marston, D.M. Dixon, J.M. Knisely, T.N. Palmore, A.S. Fauci, Antimicrobial resistance. JAMA 316, 1193–1204 (2016)
J.H. Xu, Y.L. Fan, J. Zhou, J. Het. Chem. 55, 1854 (2018)
N.R. Emmadi, C. Bingi, S.S. Kotapalli, R. Ummanni, J.B. Nanubolu, K. Atmakur, Bio. Med. Chem. Lett. 25, 2918 (2015)
C. Viegas-Junio, A. Danuello, V. da Silva Bolzani, E.J. Barreiro, C.A.M. Fraga, Curr. Med. Chem. 14, 1829 (2007)
R.K. Tittal, V.D. Ghule, N. Kumar, L. Kumar, K. Lal, A. Kumar, J. Mol. Struc. 1209, 127951 (2020)
S.R. Bonyad, Z. Mirjafary, H. Saeidian, M. Rouhani, J. Mol. Struc. 1197, 164 (2019)
M. Alizadeh, Z. Mirjafary, H. Saeidian, J. Mol. Struc. 1203, 127405 (2020)
H. Saeidian, H. Sadighian, M. Abdoli, M. Sahandi, J. Mol. Struc. 1131, 73–78 (2017)
V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int. Ed., 114, 2708 (2002)
C.W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 67, 3057 (2002)
B.S. Holla, M. Mahalinga, M.S. Karthikeyan, B. Poojary, P.M. Akberali, N.S. Kumari, Eur. J. Med. Chem. 40, 1173 (2005)
K. Lal, N. Poonia, P. Rani, A. Kumar, A. Kumar, J. Mol. Struc. 1215, 128234 (2020)
N. Poonia, K. Lal, A. Kumar, Res. Chem. Intermed. 47, 1087 (2021)
P. Yadav, K. Lal, L. Kumar, A. Kumar, A. Kumar, A.K. Paul, R. Kumar, Eur. J. Med. Chem. 155, 263 (2018)
B. Zhang, Eur. J. Med. Chem. 168, 357 (2019)
C.P. Kaushik, K. Lal, A. Kumar, S. Kumar, Med. Chem. Res. 23, 2995 (2014)
K. Lal, L. Kumar, A. Kumar, A. Kumar, Curr. Top. Med. Chem. 18, 1506 (2018)
L. Kumar, K. Lal, P. Yadav, A. Kumar, A.K. Paul, J. Mol. Struc. 1216, 128253 (2020)
M.H. Shaikh, D.D. Subhedar, L. Nawale, D. Sarkar, F.A.K. Khan, J.N. Sangshetti, B.B. Shingate, Med. Chem. Comm. 6, 1104 (2015)
R.S. Keri, S.A. Patil, S. Budagumpi, B.M. Nagaraja, Chem. Biol. Drug Des. 86, 410 (2015)
F. Mir, S. Shafi, M.S. Zaman, N.P. Kalia, V.S. Rajput, C. Mulakayala, M.S. Alam, Eur. J. Med. Chem. 76, 274 (2014)
A. Singh, C. Biot, A. Viljoen, C. Dupont, L. Kremer, K. Kumar, V. Kumar, Chem. Biol. Drug Des. 89, 856 (2017)
F. Naaz, M.P. Pallavi, S. Shafi, N. Mulakayala, M.S. Yar, H.S. Kumar, Bioorg. Chem. 81, 1 (2018)
Z. Xu, S.J. Zhao, Y. Liu, Eur. J. Med. Chem. 183, 111700 (2019)
I.S. Murthy, R. Sreenivasulu, G. Alluraiah, R.R. Raju, Russ. J. Gen. Chem. 89, 1718 (2019)
P. Yadav, K. Lal, A. Kumar, S.K. Guru, S. Jaglan, S. Bhushan, Eur. J. Med. Chem. 126, 944 (2017)
C.P. Kaushik, J. Sangwan, R. Luxmi, D. Kumar, D. Kumar, A. Das, D. Singh, J. Mol. Struc. 1226, 129255 (2021)
A. Brik, J. Alexandratos, Y.C. Lin, J.H. Elder, A.J. Olson, A. Wlodawer, C.H. Wong, Chem. Bio. Chem. 6, 1167 (2005)
M.A. Tantray, I. Khan, H. Hamid, M.S. Alam, A. Dhulap, A. Kalam, RSC adv. 6, 43345 (2016)
Y. Ke, J.J. Liang, R.J. Hou, M.M. Li, L.F. Zhao, W. Wang, H.M. Liu, Eur. J. Med. Chem. 157, 1249 (2018)
R. Kant, D. Kumar, D. Agarwal, R.D. Gupta, R. Tilak, S.K. Awasthi, A. Garwal, Eur. J. Med. Chem. 113, 34 (2016)
L.Y. Ma, L.P. Pang, B. Wang, M. Zhang, B. Hu, D.Q. Xue, H.M. Liu, Eur. J. Med. Chem. 86, 368 (2014)
N. Boechat, M.D.L.G. Ferreira, L.C. Pinheiro, A.M. Jesus, M.M. Leite, C.C. Júnior, A.U. Krettli, Chem. Biol. Drug Des. 84(3), 325 (2014)
E. Oueis, M. Jaspars, N.J. Westwood, J.H. Naismith, Angew. Chem. Int. Ed. 128, 5936 (2016)
I.E. Valverde, A. Bauman, C.A. Kluba, S. Vomstein, M.A. Walter, T.L. Mindt, Angew. Chem. Int. Ed. 52, 8957 (2013)
S.N. Malkowski, C.F. Dishuck, G.G. Lamanilao, C.P. Embry, C.S. Grubb, M. Cafiero, L.W. Peterson, Molecules 22, 1682 (2017)
M.H. Shaikh, D.D. Subhedar, F.A.K. Khan, J.N. Sangshetti, B.B. Shingate, Chine. Chem. Lett. 27, 295 (2016)
J. Lamb, W. Robson, Biochem. J. 25, 1231 (1931)
J.S. Fisk, R.A. Mosey, J.J. Tepe, Chem. Soc. Rev. 36, 1432 (2007)
E. Mavridis, E. Bermperoglou, E. Pontiki, D. Hadjipavlou-Litina, Molecules 25, 3173 (2020)
N. Sharma, J. Banerjee, N. Shrestha, D. Chaudhury, Eur. J. Biomed. Pharm. Sci. 2, 964 (2015)
R.C. Tandel, D. Mammen, Indian J. Chem. 47, 932 (2008)
G. Naganagowda, P. Thamyongkit, A. Petsom, J. Korean Chem. Soc. 55, 794 (2011)
L. Antonioli, A. El-Tayeb, C. Pellegrini, M. Fornai, O. Awwad, G. Giustarini, R. Colucci, Purinergic Signal 14, 27 (2018)
M.G. Prasad, C.V. Lakshmi, N.K. Katari, K. Anand, M. Pal, S.B. Jonnalagadda. Comb. Chem. High Throughput Screen. 625 (2019)
G. Mariappan, B.P. Saha, S. Datta, D. Kumar, P.K. Haldar, J. Chem. Sci. 123, 335 (2011)
Y.J. Rao, K. Abhijit, Russ. J. Gen. Chem. 90(6), 1074 (2020)
A. Das Mahapatra, A. Queen, M. Yousuf, P. Khan, A. Hussain, M. T. Rehman, M. I. Hassan, J. Biomol. Struct. Dyn. 1 (2020)
A. Scala, A. Piperno, N. Micale, F. Christ, Z. Debyser, A.C.S. Med, Chem. Lett. 10, 398 (2018)
MarvinSketch 19.19.0, 2019, ChemAxon.
E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, T.E. Ferrin, J. Comput. Chem. 25, 1605 (2004)
O. Trott, A.J. Olson, AutoDockVina. J. Comput. Chem. 31, 455 (2010)
Dassault Systèmes BIOVIA, Discovery studio visualizer v18.104.22.16849, San Diego: Dassault Systèmes, (2016)
The financial help from PURSE program No. SR/PURSE2/40(G), DST, New Delhi is highly acknowledged. We also acknowledge APJ Abdul Kalam Central instrumentation laboratory, Guru Jambheshwar University of Science & Technology, Hisar, India, for providing NMR and MS spectra. One of the authors (Aman Kumar) thanks University Grants Commission for the award of Junior research Fellowship.
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Kumar, L., Lal, K., Kumar, A. et al. Synthesis, antimicrobial evaluation and docking studies of oxazolone-1,2,3-triazole-amide hybrids. Res Chem Intermed (2021). https://doi.org/10.1007/s11164-021-04588-3
- Antimicrobial activity
- Docking study