Synthesis, Antibacterial and Analgesic Activities of 4‐[1‐Oxo‐3‐(substituted aryl)‐2‐propenyl]‐3‐(4‐methylphenyl) sydnones

Abstract

A series of sydnone derivatives containing styryl ketone moiety, 4-[1-oxo-3-(substituted aryl)-2-propenyl]-3-(4-methylphenyl)sydnones (6a-i) has been synthesized and characterized by spectral data. The synthesized compounds have been screened for preliminary antibacterial activity by cup plate method and analgesic activity by the method of acetic acid induced writhing in mice. The chloro and nitro derivatives showed good antibacterial activity against both gram positive and gram negative bacteria while the chloro and furyl derivatives exhibited highest analgesic effect among the series.

Fluorine bearing sydnones with styryl ketone group: synthesis and their possible analgesic and anti-inflammatory activities

“…The presence of trimethoxy group on the phenyl ring sustained activity, whereas N, N-dimethylamino group at para position did not. It is noteworthy that compounds 2a-i were found to be more active than the corresponding 4-methyl analogues reported by us earlier 8 . It is reported that intraperitoneal administration of an agent that irritates the serous membrane such as acetic acid results in the release of prostaglandins like PGE 2 and PGF 2α and sympathomimetic system mediators in the peritoneal fluid 20 .…”

“…We undertook SAR studies of 4-[1-oxo-3-(substituted aryl)-2-propenyl]-3-(3-different substituted phenyl) sydnones as analgesic and anti-inflammatory agents on the basis that molecules containing both the structural features of sydnone and styryl ketone would be better acting, because these compounds have been reported separately in literature to exhibit analgesic and antiinflammatory activities [1][2][3][4][5][6] . As a part of this, we already reported 3-(4-chlorophenyl) and 3-(4-methylphenyl) substituted compounds of the said series for analgesic and anti-inflammatory activities 7,8 . In continuation with it, we synthesized 3-(3-chloro-4-fluorophenyl) substituted compounds of the above series i.e., 4-[1-oxo-3-(substituted aryl)-2-propenyl]-3-(3-chloro-4-fluorophenyl)sydnones 2a-i, and screened them for analgesic and anti-inflammatory activities.…”

Discovery of Bis-sydnone styryl ketone as a selective cyclooxygenase-2 inhibitor

“…Last, one strong band at 835 cm −1 and another two bands at 765 and 695 cm −1 confirmed the existence of para-disubstituted and mono-substituted benzene rings in the structure of 61. Analysis of the 1 H NMR spectra of compounds 61-63 (Table 6) revealed the existence of sydnone protons, styryl protons and benzene protons within the expected ranges when compared to the spectral data of the structurally-related analogues like styryl phenyl ketone [23], styryl naphthyl ketone [22] and mon-sydnone styryl ketones [13,25]. Interestingly, the styryl protons of 62 and 63 appeared as doublets with coupling constants ≈16 Hz denoting the formation of trans conformers [23].…”

“…The CD is the largest region, and its structure is virtually similar between COX-1 and COX-2 (RMS deviation of 0.4 Å). The residues Arg120, Tyr355 and Glu524 form [2,13,22,23,25] the entrance of the active site, while Tyr385 and Tyr348 lie at the apex of the active site and they are hydrogen bonded. The main differences between both active sites are at the positions 434, 513 and 523.…”

Design synthesis and biological evaluation of 2-methylphenyl semicarbazone derivatives

“…The compounds with no substitution (compound 4) or less substitution were showed very less protection against pyrexia in comparison to the substituted compounds (Deshpande and Pai, 2010;Keri et al, 2010;Lin et al, 1997).…”