Synthesis and Pharmacological evaluation of some new Thiazolidinones and Azetidiones

Abstract

In the present study, a series of 4-thiazolidinones and 2-azetidinone newlinederivatives were synthesized by 4-naphthalen-1-yl-2-{2-[(substituted phenyl) newlinemethylidene] hydrazino}-1,3-thiazole with thioglycolic acid in presence of zinc newlinechloride as a catalyst and dioxane as a solvent and azetidinones were synthesized newlineby a solution of chloroacetyl chloride (0.02 moles) in dry dioxane (30 ml) was newlineadded drop wise below 10 °C to a well stirred solution of 4-(1-naphthyl)-2- newline(substitutedbenzylidineamino)-1,3-thiazoles (SB1-SB15) (0.01 mole) and newlinetriethylamine (0.02 moles) in dimethylformamide (10 ml). The solution was newlinestirred for 8-10 hr. The reaction mixture was filtered (to remove precipitates of newlinetriethylamine hydrochloride) and poured into ice cold water. The resulting solid newlinewas separated by vacuum filtration and dried. The compound was recrystallized newlinefrom dioxane. The chemical structures of the synthesized compounds were newlineconfirmed by means of IR, 1H-NMR, mass spectroscopy and elemental analysis. newlineThese compounds were screened for anti inflammatory, analgesic, anti newlineconvulsant, anti hyperglycaemic, Anti anxiety and Anti tubercular activites. The newlinecompound TA1 exhibited highest activity followed by TA8, TA6, TA5, TA4 and newlineTA10. It was also observed that blood glucose lowering effects were more newlinepronounced and stronger in alloxan model. Anticonvulsant activity of [2- newline(substitutedphenyl)-3-[{4-(1-naphthyl)-1, 3-thiazo1-2- yl} amino] -4-oxo- 1, 3 - newlinethiazolidin-5 -yl] acetic acid (TA1-TA10) revealed that compounds TA7 (Ar = 4- newlinebromo-2-hydroxyphenyl) and TA8 (Ar = 4-chloro-2- hydroxyphenyl) showed newlinehighest anticonvulsant activity with respect to phenytoin but it was only 40% of newlinethe activity shown by phenytoin. All other compounds exhibited mild newlineanticonvulsant activity. newline newline