Synthesis of phthalimido or succinimido-[2-aryl-4-oxo-3-[{2-oxo-2-(phcnothiazin-10-yl)ethyllamino]-1,3-thiazolidin-5-yl]cthanoate and their antimicrobial activities

摘要

Keeping in view the pharmacological potential of thiazolidinones and phenothiazines, the title compounds containing these nuclei have been synthesized. Reaction of 10-(chloroacctyl)phcnothiazine 1 with hydrazine hydrate gives 10-(hydrazinoacctyl)phcnolhiazinc 2, which on treatment with various aromatic aldehydes yields 10-[4-(aryIidenc)hydrazino acetyl] phcnolhiazine 3a-d. These Schiff bases 3a-d underwent cyclization when treated with mcrcaptosuccinic acid in presence of anhydrous zinc chloride to give [2-aryl-4-oxo-3-[{2-oxo-2-(phenothiazin-10-yl)ethylJamino]-1,3-thiazolidin-5-yl|ethanoic acid 4a-d, which are converted to [2-aryl-4-oxo-3-[{2-oxo-2-(phcnolhiazin-10-yl)ethyI}amino]-1,3-lhiazoIidin-5-yl] cthanoyl chloride 5a-d on reaction with thionyl chloride. Subsequent treatment of 5a-d with AMiydroxyphthalimide or A'-hydroxysuccinimide furnished phthalimido or succinimido-[2-aryl-4-oxo-3-[{2-oxo-2-(phenothiazin-10-yl)elhyl}amino]-l,3-thiazo!idin-5-yl]cthanoatc 6a-h. The constitution of all the above products have been supported by elemental analysis and spectral studies. Antibacterial and antifungal activities of the final compounds have been evaluated and all the compounds have shown significant inhibition of bacterial and fungal growth.