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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: N-Hydroxysuccinimide;N-hydroxyphthalimide;phenothiazine;antimicrobial activity;thiazolidine
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 1 with hydrazine hydrate gives 10-(hydrazinoacetyl)phenothiazine 2, which on treatment with various aromatic aldehydes yields 10-[4-(arylidene)hydrazino acetyl] phenothiazine 3a-d. These Schiff bases 3a-d 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 4a-d, which are converted to [2-aryl-4-oxo-3-[{2-oxo-2-(phenothiazin-10-yl)ethyl}amino]-1,3-thiazolidin-5-yl] ethanoyl chloride 5a-d on reaction with thionyl chloride. Subsequent treatment of 5a-d with N-hydroxyphthalimide or N-hydroxysuccinimide furnished phthalimido or succinimido-[2-aryl-4-oxo-3-[{2-oxo-2-(phenothiazin-10-yl)ethyl}amino]-1,3-thiazolidin-5-yl]ethanoate 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.
Page(s): 1583-1589
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.48B(11) [November 2009]

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