Microwave-assisted synthesis of new pyrazole derivatives bearing 1,2,3-triazole scaffold as potential antimicrobial agents

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Dongamanti Ashok
Rangu Kavitha
Srinivas Gundu
Velagapuri Hanumantha Rao

Abstract

A new series of (E)-3-(3-(4-substituted phenyl)-1-phenyl-1H-pyr­azol-4-yl)-1-(2-hydroxy-4-((1-aryl-1H-1-2,3-triazol-4-yl)methoxy)phenyl)­prop-2-en-1-one derivatives was synthesized. The synthesis of the title com­pounds involved the 1,3-dipolar Cu(I)-catalyzed alkyne–azide cycload­dition (CuAAC) reaction of (E)-3-(3-(4-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl)-1-(2-hydroxy-4-(prop-2-yn-1-yloxy)phenyl)prop-2-en-1-ones with aro­matic azides. The structures were confirmed by NMR, FT-IR, mass and ele­mental analysis. All the synthesized compounds (6aj) were evaluated for their antimicrobial activity. Compounds 6a, 6d and 6e demonstrated promising inhibitory effects on both bacterial and fungal strains.

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How to Cite
[1]
D. Ashok, R. Kavitha, S. Gundu, and V. Hanumantha Rao, “Microwave-assisted synthesis of new pyrazole derivatives bearing 1,2,3-triazole scaffold as potential antimicrobial agents”, J. Serb. Chem. Soc., vol. 82, no. 4, pp. 357–366, May 2017.
Section
Organic Chemistry
Author Biography

Dongamanti Ashok, Green and Medicinal Chemistry Laboratory, Department of Chemistry, Osmania University, Hyderabad- 500 007

Professor in Chemistry

Dept. of Chemistry

Osmania University

References

M. Grare, M. Mourer, S. Fontanay, J. B. Regnouf-de-Vains, C. Finance, R. E. Duval, J. Antimicrob. Chemother. 60 (2007) 575

A. Coates, Y. Hu, R. Bax, C. Page, Nat. Rev. Drug Discov. 1 (2002) 895

R. Storer, C. J. Ashton, A. D. Baxter, M. M. Hann, C. L. P. Marr, A. M. Mason, C. L. Mo, P. L. Myers, S. A. Noble, C. R. Penn, N. G. Weir, J. M. Woods, P. L. Coe, Nucleosides Nucleotides 18 (1999) 203

N. Gokhan-Kelekci, S. Yabanoglu, E. Kupeli, U. Salgin, O. Ozgen, G. Ucar, E. Yesilada, E. Kendi, A. Yesilada, A. A. Bilgin, Bioorg. Med. Chem. 15 (2007) 5775

D. Kaushik, S. A. Khan, G. Chawla, S. Kumar, Eur. J. Med. Chem. 45 (2010) 3943

A. Balbi, M. Anzaldi, C. Macciò, C. Aiello, M. Mazzei, R. Gangemi, P. Castagnola, M. Miele, C. Rosano, M. Viale, Eur. J. Med. Chem. 46 (2011) 5293

F. Colliot, K. A. Kukorowski, D. W. Hawkins, D. A. Roberts, Brighton Crop Prot. Conf.–Pests Dis. 1 (1992) 29

H. S. Chen, Z. M. Li, Y. F. Han, J. Agric. Food Chem. 48 (2000) 5312

C. B. Vicentini, C. Romagnoli, E. Andreotti, D. Mares, J. Agric. Food Chem. 55 (2007) 10331

H. C. Kolb, K. B. Sharpless, Drug Discovery Today 8 (2009) 1128

S. G. Agalave, S. R. Maujan, V. S. Pore, Chem. Asian J. 6 (2011) 2696

V. V. Rostovtsev, K. B. Sharpless, Angew. Chem. Int. Ed. 41 (2002) 2596

H. Saqlain, A. Mohammad Sarwar, H. Hinna, S. Syed, D. Abhijeet, H. Firasat, A. Perwez, U. Sadiq, M. A. Q. Pasha, B. Sameena, N. Syed, A. Yakub, K. Chetna, Eur. J. Med. Chem. 81 (2014) 204

J. M. Xu, E. Zhang, X. J. Shi, Y. C. Wang, B. Yu, W. W. Jiao, Y. Z. Guo, H. M. Liu, Eur. J. Med. Chem. 80 (2014) 593

Y. S. Sanghvi, B. K. Bhattacharya, G. D. Kini, S. S. Matsumoto, S. B. Larson, W. B. Jolley, R. K. Robins, G. R. Revankar, J. Med. Chem. 33 (1990) 336

M. Journet, D. Cai, J. J. Kowal, R. D. Larsen, Tetrahedron Lett. 42 (2001) 9117

M. D. Chen, S. J. Lu, G. P. Yuag, S. Y. Yang, X. L. Du, Heterocycl. Comm. 6 (2000) 421

S. Shafi, M. M. Alam, N. Mulakayala, C. Mulakayala, G. Vanaja, A. M. Kalle, R. Pallu, M. S. Alam, Eur. J. Med. Chem. 49 (2012) 324

N. Upmanyu, J. K. Gupta, K. Shah, P. Mishra, Pharm. Chem. J. 45 (2011) 433

K. M. Banu, A. Dinakar, C. Ananthanarayanan, Indian J. Pharm. Sci. 4 (1999) 202

L. P. Guan, Q. H. Jin, G. R. Tian, K. Y. Chai, Z. S. Quan, J. Pharm. Pharm. Sci. 10 (2007) 254

A. Passannanti, P. Diana, P. Barraja, F. Mingoia, A. Lauria, G. Cirrincione, Heterocycles 48 (1998) 1229

M. Jilino, F. G. Stevens, J. Chem. Soc. Perkin Trans. 1 (1998) 1677

L. Zhou, A. Amer, M. Korn, R. Burda, J. Balzarini, E. De Clercq, E. R. Kern, P. F. Torrence, Antivir. Chem. Chemother. 16 (2005) 375

D. Ashok, D. M. Gandhi, G. Srinivas, A. V. Kumar, Med. Chem. Res. 23 (2014) 3005

D. Ashok, G. Srinivas, A. V. Kumar, D. M. Gandhi, S. R. Malladi, Russ. J. Gen. Chem. 85 (2015) 708

D. Ashok, L. B. Vijaya, S. Ravi, A. Ganesh, Med. Chem. Res. 24 (2015) 1487

P. Sreenivas, S. S. Reddy, Y. J. Rao, Ch. P. Rao, G. L. D. Krupadanam, Indian J. Chem. Sect. B 50 (2011) 1484

D. Ashok, K. Rangu, V. Hanumantha Rao, S. Gundu, B. Srilata, M. Vijjulatha, Med. Chem. Res. 25 (2016) 501

K. T. Chung, W. R. Thomasson, C. D. Wu-Yuan, J. Appl. Bacteriol. 69 (1990) 498

C. Azoro, World J. Biotechnol. 3 (2002) 347

D. Janovska, K. Kubikova, L. Kokoska, J. Food Sci. 21 (2003) 107

J. Bishnu, L. Sunil, S. Anuja, J. Sci. Eng. Technol. 5 (2009) 143.

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