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Title: Synthesis of phthalimido or succinimido-[2-aryl-4-oxo-3-[{2-oxo-2-(phenothiazin-10-yl)ethyl}amino]-1,3-thiazolidin-5-yl]ethanoate and their antimicrobial activities
Authors: Salvi, Vijay Kumar
Sharma, Shweta
Sharma, Chirag
Bhambi, Dinesh
Talesara, G L
Keywords: <i>N</i>-Hydroxysuccinimide
antimicrobial activity
Issue Date: Nov-2009
Publisher: CSIR
Abstract: Keeping in view the pharmacological potential of thiazolidinones and phenothiazines, the title compounds containing these nuclei have been synthesized. Reaction of 10-(chloroacetyl)phenothiazine <b style="">1</b> with hydrazine hydrate gives 10-(hydrazinoacetyl)phenothiazine <b style="">2</b>, which on treatment with various aromatic aldehydes yields 10-[4-(arylidene)hydrazino acetyl] phenothiazine <b style="">3a-d</b>. These Schiff bases <b style="">3a-d</b> underwent cyclization when treated with mercaptosuccinic acid in presence of anhydrous zinc chloride to give [2-aryl-4-oxo-3-[{2-oxo-2-(phenothiazin-10-yl)ethyl}amino]-1,3-thiazolidin-5-yl]ethanoic acid <b style="">4a-d</b>, which are converted to [2-aryl-4-oxo-3-[{2-oxo-2-(phenothiazin-10-yl)ethyl}amino]-1,3-thiazolidin-5-yl] ethanoyl chloride <b style="">5a-d</b> on reaction with thionyl chloride. Subsequent treatment of <b style="">5a-d</b> with <i style="">N</i>-hydroxyphthalimide or <i style="">N</i>-hydroxysuccinimide furnished phthalimido or succinimido-[2-aryl-4-oxo-3-[{2-oxo-2-(phenothiazin-10-yl)ethyl}amino]-1,3-thiazolidin-5-yl]ethanoate <b style="">6a-h</b>. 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.<b> </b>
Description: 1583-1589
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.48B(11) [November 2009]

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