Further derivatives of 4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carboxylic acid and their antibacterial activities

Abstract

Compound 4, 5, 6, 7, and 8 were synthesized from 4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carboxylic acid 1 as a starting material. The pyrazolo[4,3-d]oxazinone 4 was obtained from direct reaction of the acid 1 with hydroxylamine hydrochloride. Acid chloride 2 was converted easily into the new derivatives consisting of 1-(4-benzoyl-1,5-diphenyl-1H-pyrazol-3-oyl)-sulfamide 5 and 3,4-dibenzoyl-1,5-diphenyl-1H-pyrazole 6. The nitrile derivative 7 was obtained by dehydration of the amide 3 in a mixture of SOCl 2 and Dimethylformamide (DMF). Cyclocondensation reaction of 7 with anhydrous hydrazine led to the formation of 7-aminopyrazolo[3,4-d]pyridazine 8 derivative. These new synthesized compounds evaluated for their antibacterial activities against Gram-positive and Gram-negative bacteria using the tube dilution method. The finding of antibacterial activity study showed that the sulfamide derivative 5 was the best compound of the series, exhibiting antibacterial activity against both Gram-positive and Gram-negative bacteria.

Phytochemicals from Ficus sycomorus L. leaves act as insecticides and acaricides

“…Molecules of many modern drugs, e.g., antiphlogistic, antifungal, antidiabetic, and analgesic, as well on insectacaricide used in practice, contain a pyrazole ring as a fragment (Bildirici et al, 2007). The pyrazole ring has been shown to be the basic for a few antibacterial substances (Adnan et al, 2009).…”

Synthesis and antibacterial activity of 4-benzoyl-1-(4-carboxy-phenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid and derivatives

“…The results obtained clearly indicate that the series of newly synthesized compounds discussed here are active against a select subset of the human pathogenic bacteria investigated herein. Since 1H-pyrazole-3-carboxylic acids were already reported to be microbicides and herbicides (Bildirici et al, 2007;Mahajan et al, 1991;Sridhar et al, 2004;Sivaprasad et al, 2006) the corresponding amide derivatives of the 1H-pyrazole-3-carboxylic acid discussed herein are also expected to exhibit similar activities. This finding may promote the synthesis of more active 1H-pyrazole-3-carboxylic acids in the future.…”

“…Pyrazole chemistry has been a focus of medical research for more than three decades due to the versatile biological and pharmacological activities of pyrazole derivatives, including effects as antimicrobial (Bildirici et al, 2007;Mahajan et al, 1991;Sridhar et al, 2004;Sivaprasad et al, 2006), antiviral (Baraldi et al, 1998;Janus et al, 1999), antitumor (Suzuki and Inoue, 1990;Hatheway et al, 1978;Katayama and Oshiyama, 1997;Manfredini et al, 1992), anti-inflammatory (Badawey and El-Ashmawey, 1998;Bruno et al, 1992;Manfredini et al, 1996;Tewari and Mishra, 2001), antihistaminic (Mishra et al, 1998), pesticidal (Londershausen, 1996), antifungal (Badiger and Bennur, 1996;Graneto and Phillips, 1992), anti-rheumatoid-arthritic (Kurowski et al, 1986), anticonvulsant (Lepage and Hublot, 1992), antidepressant (Bailey et al, 1985), and antipyretic (Wiley and Wiley, 1964) agents. Recently, several papers have reported the synthesis of potential biologically active compounds containing pyrazolo [3,4-d]pyridazine systems (Matyus, 1998;Ö nal et al, 1996).…”

Regioselective synthesis of some functionalized 3,4’-bis-(pyrazolyl)ketones and chemoselectivity in their reaction with hydrazine hydrate

“…At present, there are several review articles by Shawali et al covering their reactions and applications [1][2][3][4][5][6][7][8][9]. Also, literature reports indicate that many pyrazole derivatives found use in various pharmaceutical, agrochemical and many other applications [10][11][12][13][14][15][16][17]. In the light of these facts and in conjunction with our ongoing studies of the chemistry of hydrazonoyl halides, it was thought interesting to study the 1,3-dipolar cycloaddition of the nitrilimines derived from hydrazonoyl halides to the enamino ester, namely (E)-ethyl 3-(dipropylamino)-acrylate 1, which has not been reported hitherto.…”