Microwave-assisted synthesis and antimicrobial evaluation of 6-[3-aryl-1-phenyl-4′,5′-dihydro[4,5′-bi-1H-pyrazol]-3′-yl]-2H-chromen-5-ols
Main Article Content
Abstract
A new series of 6-[3-aryl-1-phenyl-4′,5′-dihydro[4,5′-bi-1H-pyrazol]-3′-
-yl]-2H-chromen-5-ol derivatives was synthesized by Michael addition of chalcones 5a–j with hydrazine hydrate in presence of sodium acetate under conventional heating and microwave irradiation. Structural assignment of the products was confirmed based on IR, 1H-NMR, 13C-NMR, MS and analytical data. All the synthesized compounds 6a–j were screened for their antimicrobial activity against various bacterial and fungal strains. Most of the compounds exhibited variable range of antimicrobial activity and compounds 6c–f and 6i showed promising antimicrobial potency.
Downloads
Metrics
Article Details
Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution license 4.0 that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
References
K. Chrag, C. S. Patel, B. Rami, C. N. Panigrahi, J. Chem. Pharm. Res. 2 (2010) 73
D. V. Dekhane, S. S. Pawar, S. Gupta, M. S. Shingare, C. R. Patil, S. N. Thore, Bioorg. Med. Chem. Lett. 21 (2011) 6527
C. Y. Zhang, X. H. Liu, B. L. Wang, S. H. Wang, Z. M. Li, Chem. Biol. Drug Design 75 (2010) 489
Z. Yuhan, X. Na, W. Guowei, Q. Jingping, J. Chem. Res. 34 (2014) 684
B. L. Finkelstein, C. J. Strock, Pest. Sci. 50 (1997) 324
S. A. F. Rostom, M. A. Shalaby, M. A. El-Demellawy, Eur. J. Med. Chem. 38 (2003) 959
O. I. El-Sabbagh, M. M. Baraka, S. M. Ibrahim, C. Pannecouque, G. Andrei, R. Snoeck, J. Balzarini, A. A. Rashad, Eur. J. Med. Chem. 44 (2009) 3746
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
R. R. Ranatunge, D. S. Garvey, D. R. Janero, L. G. Letts, A. M. Martino, M. G. Murty, S. K. Richardson, D. V. Young, I. S. Zemetseva, Bioorg. Med. Chem. 12 (2004) 1357
T. M. Fong, S. B. Heymsfield, Int. J. Obes. 33 (2009) 947
S. M. Sakya, H. Cheng, K. M. Lundy DeMello, A. Shavnya, M. L. Minich, B. Rast, J. Dutra, C. Li, R. J. Rafka, D. A. Koss, J. Li, B. H. Jaynes, C. B. Ziegler, D. W. Mann, C. F. Petras, S. B. Seibel, A. M. Silvia, D. M. George, A. Hickman, M. L. Haven, M. P. Lynch, Bioorg. Med. Chem. Lett. 16 (2006) 1202
M. I. Husain, S. Shukla, Indian J. Chem., B 25 (1986) 983
V. H. Babu, C. H. Sridevi, A. Joseph, K. K. Srinivasan, Ind. J. Pharm. Sci. 69 (2007) 470
F. F. Barsoum, H. M. Hosni, A. S. Girgis, Bioorg. Med. Chem. 14 (2006) 3929
Y. K. Agrawal, K. Manna, V. H. Babu, K. K. Srinivasan, H. Bhatt, P. J. Gogoi, Indian J. Heterocycl. Chem.16 (2007) 263
M. Abid, A. Azam, Eur. J. Med. Chem. 40 (2005) 935
M. Amir, H. Kumar, S. A. Khan, Bioorg. Med. Chem. Lett. 18 (2008) 918
A. M. Fahmy, K. M. Hassa, A. A. Khalaf, R. A. Ahmed, Indian J. Chem. 26 (1987) 884
R. A. Nugent, M. Murphy, S. T. Schlachter, C. J. Dunn Smith R. J. Staite L. A. Galinet, S. K. Shields, D. G. Aspar, K. A. Richard, N. A. Rohloff, J. Med. Chem. 36 (1993) 134
S. Rich, J. G. Horsfall, CA 46 (1952) 11543
H. Kawazura, Y. Takahashi, Y. Shinga, F. Shimanda, N. Ohto, A. Tamura, Jpn. J. Pharmacol. 73 (1997) 317
E. Palaska, M. Aytemir, T. Uzbay, D. Erol, Eur. J. Med. Chem. 36 (2001) 539
S. A. Wadhal, K. N. Wadokar, P. S. Pande, Indian J. Heterocycl. Chem. 15 (2005) 11
E. L. Anderson, J. E. Casey, L. C. Greene, J. J. Lafferty, H. E. Reiff, J. Med. Chem. 7 (1984) 25
H. J. Benson, Microbiological applications, 5th ed, W. C. Brown Publications, Boston, MA, 1990.
P. Sreenivas, 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