Abstract
In Search of novel antimicrobial agents with improved potency, we designed and synthesized a series of 3-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)-2-(4-fluorophenyl)-4H-chromen-4-ones 5a–f using click chemistry. The structures of synthesized compounds were found using IR, 1H NMR, 13C NMR, and MS. All the synthesized compounds were assayed for their in vitro antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa and antifungal activity against Candida albicans, Candida glabrata, and Candida tropicalis by micro broth dilution method. The antimicrobial data suggested that from the series, compounds 3e, 4e, 5e, and 5f shows pronounced antimicrobial activity against the tested strain with low MIC value. Molecular docking study was used to rationalize binding interaction at the active site and the results showed good binding interaction.
Graphical Abstract
Similar content being viewed by others
References
R.P. Mishra, E. Oviedo-Orta, P. Prachi, R. Rappuoli, F. Bagnoli, Curr. Opin. Microbiol. 15, 596 (2012)
N. Nair, W. Kudo, M.A. Smith, R. Abrol, W.A. Goddard, V.P. Reddy, Bioorg. Med. Chem. Lett. 21, 3957 (2011)
M.Y. Anzahaee, J.K. Watts, N.R. Alla, A.W. Nicholson, M.J. Damha, J. Am. Chem. Soc. 133, 728 (2011)
W. Zhu, C. Chen, C. Sun, S. Xu, C. Wu, F. Lei, H. Xia, Q. Tu, P. Zheng, Eur. J. Med. Chem. 93, 64 (2015)
A. Dongamanti, V.K. Aamate, M.G. Devulapally, S. Gundu, M.K. Kotn, V. Manga, S. Balasubramanian, P. Ernala, Bioorg. Med. Chem. Lett. 25, 898 (2015)
N. Pandurangan, C. Bose, A. Banerji, Bioorg. Med. Chem. Lett. 21, 5328 (2011)
P.M. Kris-Etherton, K.D. Hecker, A. Bonanome, S.M. Coval, A.E. Binkoski, K.F. Hilpert, A.E. Griel, T.D. Etherton, Am. J. Med. 113, 71 (2002)
A. Garcıa-Lafuente, E. Guillamon, A. Villares, M.A. Rostagno, J.A. Martınez, Inflamm. Res. 58, 537 (2009)
V.C. Patil, IJPSR. 3, 5006 (2012)
C. Chiruta, D. Schubert, R. Dargusch, P. Maher, J. Med. Chem. 55, 378 (2012)
R. Pingaew, A. Saekee, P. Mandi, C. Nantasenamat, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, Eur. J. Med. Chem. 85, 65 (2014)
M. Fathimunnisa, H. Manikandan, S. Selvanayagam, J. Mol. Struct. 1099, 407 (2015)
K.V. Sashidhara, S.R. Avula, P.K. Doharey, L.R. Singh, V.M. Balaramnavar, J. Gupta, S. Misra-Bhattacharya, S. Rathaur, A.K. Saxena, J.K. Saxena, Eur. J. Med. Chem. 103, 418 (2015)
S. Vogel, M. Barbic, G. Jurgenliemk, J. Heilmann, Eur. J. Med. Chem. 45, 2206 (2010)
B.P. Bandgar, S.S. Gawande, R.G. Bodade, J.V. Totre, C.N. Khobragade, Bioorg. Med. Chem. 18, 1364 (2010)
S. Padhye, A. Ahmad, N. Oswal, P. Dandawate, R.A. Rub, J. Deshpande, K.V. Swamy, F.H. Sarkar, Bioorg. Med. Chem. Lett. 20, 5818 (2010)
H.C. Kolb, M.G. Finn, K.B. Sharpless, Angew. Chem. Int. Ed. 40, 2004 (2001)
R. Huisgen, Angew. Chem. Int. Ed. 75, 604 (1963)
V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int. Ed. 41, 2596 (2002)
C.W. Tornøe, C. Charistensen, M. Meldal, J. Org. Chem. 67, 3057 (2002)
S.G. Agalave, R.S. Maujan, V.S. Pore, Chem. Asian J. 6, 2696 (2011)
M.H. Shaikh, D.D. Subhedar, M. Arkile, V.M. Khedkar, N. Jadhav, D. Sarkar, B.B. Shingate, Bioorg. Med. Chem. Lett. 26, 561 (2016)
P.S. Rao, C. Kurumurthy, B. Veeraswamy, G.S. Kumar, Y. Poornachandra, C.G. Kumar, S.B. Vasamsetti, S. Kotamraju, B. Narsaiah, Eur. J. Med. Chem. 80, 184 (2014)
J. Sindhu, H. Singh, J.M. Khurana, C. Sharma, K.R. Aneja, Chin. Chem. Lett. 26, 50 (2015)
E.A. Sherement, V. Berestovitsk, Russ. J. Org. Chem. 40, 594 (2004)
B.S. Holla, N.S. Kumari, Eur. J. Med. Chem. 40, 1173 (2005)
L. Gavara, P. Moreau, Eur. J. Med. Chem. 45, 5520 (2010)
I.E. G1owacka, J. Balzarini, A.E. Wróblewski, Eur. J. Med. Chem. 70, 703 (2013)
Y. Chinthala, S. Thakur, S. Tirunagari, S. Chinde, A.K. Domatti, N.K. Arigari, K.V.N.S. Srinivas, S. Alam, K.K. Jonnala, F. Khan, A. Tiwari, P. Grover, Eur. J. Med. Chem. 93, 564 (2015)
N.R. Emmadi, C. Bingi, S.S. Kotapalli, R. Ummanni, J.B. Nanubolu, K. Atmakur, Bioorg. Med. Chem. Lett. 25, 2918 (2015)
H. Akrami, B.F. Mirjalili, M. Khoobi, A. Moradi, H. Nadri, S. Emami, A. Foroumadi, M. Vosooghi, A. Shafiee, Arch. Pharm. Chem. Life Sci. 348, 366 (2015)
L. Pinhua, W. Lei, Lett. Org. Chem. 4, 23 (2007)
M.D. Nikam, P.S. Mahajan, M.G. Damale, J.N. Sangshetti, A.V. Chate, S.K. Dabhade, C.H. Gill, Lett. Drug Des. Discov. 12, 8 (2015)
A. Dongamanti, V.K. Aamate, M.G. Devulapally, S. Gundu, M.K. Kotni, V. Manga, S. Balasubramanian, P. Ernala, Bioorg. Med. Chem. Lett. 25, 898 (2015)
M. Gharpure, R. Choudhary, V. Ingle, H. Juneja, J. Chem. Sci. 125, 575 (2013)
N. Kumar, S. Kumar, H. Gupta, P.K. Sharma, World Res. J. Biochem. 1, 01 (2012)
Acknowledgments
Author V.S.D. is very grateful to the Council of Scientific and Industrial Research (CSIR), New Delhi, India, for providing Senior Research Fellowship and Sophisticated Analytical Instrumentation Facility (SAIF), Panjab University, Chandigarh for providing spectral data. We are thankful to Head, Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, Maharashtra, for providing laboratory facility. We are also thankful to the Rajarshi Shahu College, Latur, for providing biological activities.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Dofe, V.S., Sarkate, A.P., Lokwani, D.K. et al. Synthesis, antimicrobial evaluation, and molecular docking studies of novel chromone based 1,2,3-triazoles. Res Chem Intermed 43, 15–28 (2017). https://doi.org/10.1007/s11164-016-2602-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-016-2602-z