Synthesis, Antioxidant and Antimicrobial Activities of a Novel Series of Chalcones, Pyrazolic Chalcones, and Allylic Chalcones

Tan Nhut Doan, Dao Thanh Tran
DOI: 10.4236/pp.2011.24036                

Abstract

A new series of chalcones (4a-c) and allylicchalcones (11a-b) have been prepared by the Claisen-Schmidt condensation. A novel series of pyrazolicchalcones (5a-c) have been synthesized by the reaction of respective chalcones (4a-c) and hydrazine hydrate. The structures of the compounds were confirmed by spectral data (infrared spectroscopy and ¹H nuclear magnetic resonance). All of the compounds (4/5a-c and 11a-b) have been tested for their antimicrobial activities (agar disc-diffusion method) and antioxidant activities (1,1-biphenyl-2-picrylhydrazyl free radical scavenging method). The test compounds failed to show antibacterial properties (4a-c, 5b, and 11a-b) or exhibited such properties poorly (5a and 5c). None of the test compounds displayed antifungal properties. Of the compounds tested, compounds 5a-c and 11a-b exhibited promising antioxidant activities.

Keywords

AllylicChalcones, Antioxidant Activity, Antimicrobial Activity, PyrazolicChalcones

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	E. Grotewold, “The science of flavonoids”, Springer, New York, 2006.
[2]	Y.M. Lin, Y. Zhou, M. Flavin, L.M. Zhou, W. Nie and F.C. Chen, “Chalcones and flavonoids as anti-tuberculosis agents”, Bioorganic & Medicinal Chemistry, Vol. 10, 2002, pp. 2795-2802.
[3]	M.L. Go, X. Wu and X.L. Liu, “Chalcones: an update on cytotoxic and chemoprotective properties”, Current Medicinal Chemistry, Vol. 12, 2005, pp. 483-499.
[4]	Z. Nowakowska, “A review of anti-infective and anti-inflammatory chalcones”, European Journal of Medicinal Chemistry, Vol. 42, 2007, pp. 125-137.
[5]	S. Velavan, K. Nagulendran, R. Mahesh and V. Begum, “In vitro antioxidant activity of Asparagus racemosusroot”, Pharmacognosy Magazine, 1998, ISSN: 0973- 1296.
[6]	M. Okawa, J. Kinjo, T. Nohara and M. Ono, “DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity of flavonoids obtained from some medicinal plants”, Biological and Pharmaceutical Bulletin, Vol. 24, 2001, pp. 1202-1205.
[7]	E. Cadenas and L. Packer, “Handbook of antioxidants”, Marcel Dekker, New York, 1996.
[8]	C. Rice-Evans and L. Packer, “Flavonoids in health and disease”, Marcel Dekker, New York, 2003.
[9]	Prakash, R. Kumar and V. Parkash, “Synthesis and antifungal activity of some new 3-hydroxy-2-(1-phenyl-3- aryl-4-pyrazolyl)chromones”, European Journal of Medicinal Chemistry, Vol. 43, 2008, pp. 435-440.
[10]	Prakash, R. Kumar and R. Sehrawat, “Synthesis and antibacterial activity of some new 2,3-dimethoxy-3-hydroxy- 2-(1-phenyl-3-aryl-4-pyrazolyl)chromanones”, European Journal of Medicinal Chemistry, Vol. 44, 2009, pp. 1763- 1767.
[11]	B. Bandgar, S. Gawande, R. Bodade, N. Gawande and C. Khobragade, “Synthesis and biological evaluation of a novel series of pyrazolechalcones as anti-inflammatory, antioxidant and antimicrobial agents”, Bioorganic & Medicinal Chemistry, Vol. 17, 2009, pp. 8168-8173.
[12]	H. Adibi, J.S. Mojarrad, H. Asgharloo and G. Zarrini, “Synthesis, in vitro antimicrobial and antioxidant activities of chalcone and flavone derivatives holding allylic substitutions”, Medicinal Chemistry Research, 2010, pp. 1-7.
[13]	N.S. Joshi, A.A. Shaikh, A.P. Deshpande, B.K. Karale, S.B. Bhirud and C.H. Gill, “Synthesis, characterization and antimicrobial activities of some fluorine containing 2 (1-phenyl-3-aryl-1H-pyrazol-4-yl)-3-chlorochromones, 2- (1-Phenyl-3-aryl-1H-pyrazol-4-yl)chromones and 5-(1- phenyl-3-aryl-1H-pyrazol-4-yl)-3-(2-hydroxyphenyl)-4,5-dihydropyrazolines”, Indian Journal of Chemistry, Vol. 44B, 2005, pp. 422-425.
[14]	TT. Dao, Y.S. Chi, J. Kim, H.P. Kim, S. Kim and H. Park, “Synthesis and PGE2 inhibitor activity of 5,7-dihydroxy- flavones and their O-methylate flavone analogs”, Archives of Pharmacal Research, Vol. 26, 2003, pp. 345-350.
[15]	M. Hiersemann and U. Nubbemeyer, “The Claisen rearrangement: methods and applications”, Wiley-VCHVerlag GmbH, Weinheim, 2007.
[16]	NCCLS - National Committee for Clinical Laboratory Standards (1985) Approved standard document M-7A, Villanova, P.A., 1985.
[17]	P.R. Murray, E. Baron, J. Jorgensen, M. Landry and M. Pfaller, “Manual of clinical microbiology” (9th ed), American Society of Microbiology, Washington D.C., 2007.
[18]	K. Kato, S. Terao, N. Shimamoto and M. Hirata, “Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids”, Journal of Medicinal Chemistry, Vol. 31, 1988, pp. 793-798.
[19]	Padmaja, T. Payani, G.D. Reddy and V. Padmavathi, “Synthesis, antimicrobial and antioxidant activities of substituted pyrazoles, isoxazoles, pyrimidine and thioxopyrimidine derivatives”, European Journal of Medicinal Chemistry, Vol. 44, 2009, pp. 4557-4566