Synthesis and Biological Activity Evaluation of Some Azetidinone and Thiazolidinone Derivatives of Coumarins

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Title Synthesis and Biological Activity Evaluation of Some Azetidinone and Thiazolidinone Derivatives of Coumarins
 
Creator BB Subudhi; University Department of Pharmaceutical Sciences, Utkal University, Vanivihar, Bhubaneshwar-751004, Orissa, India
PK Panda; University Department of Pharmaceutical Sciences, Utkal University, Vanivihar, Bhubaneshwar-751004, Orissa, India
BK Tosh; University Department of Pharmaceutical Sciences, Utkal University, Vanivihar, Bhubaneshwar-751004, Orissa, India
S Sahu; University Department of Pharmaceutical Sciences, Utkal University, Vanivihar, Bhubaneshwar-751004, Orissa, India
P Majhi; University Department of Pharmaceutical Sciences, Utkal University, Vanivihar, Bhubaneshwar-751004, Orissa, India
 
Subject Pharmacy
Azetidinones; thiazolidinone; coumarin; nitrofurantoin; E. coli; P. auregenosa; K. pneumoniae; P. mirabilis; E. faecalis; S.aureus
 
Description Keeping in view the pharmacological potential of azetidinones, thiazolidinones and coumarins, the title compounds containing these nuclei were synthesized. The 4-methyl -7-hydroxy coumarin (1) on treatment with hydrazine hydrate affords 2-hydrazo- 4-methyl -7-hydroxy coumarin (2). The N- (2’-imino-4’-methyl-7’-hydroxy coummarinyl)-imino substituted benzene (3) was synthesized by reaction of compound 2 with various aromatic aldehydes. Condensation of compound 3 with chloroacetyl chloride in presence of 1,4-dioxan and triethyl amine yields the 3-chloro-4- (substituted)-1-(2’-imino-4’-methyl-7’-hydroxy coumarinyl) azetidin-2-one (4a-d). Further more condensation of 3 with thioglycollic acid in presence of 1,4-dioxan and anhydrous aluminium chloride gives 2-(substituted phenyl)-3-(2’-imino-4’-methyl-7’-hydroxy coumarinyl)-1,3-thiazolidinone (4’a-d). Elemental and spectral characterization established the identity of these compounds. All the products were screened in vitro for their anti microbial activity against different strains of urinary tract pathogens. All compounds exhibited significant antimicrobial activity compared to the standard drug nitrofurantoin. Key words: Azetidinones, thiazolidinone, coumarin, nitrofurantoin, E. coli, P. auregenosa, K. pneumoniae, P. mirabilis E. faecalis, and S.aureus. Dhaka Univ. J. Pharm. Sci. Vol.4(2) 2005 The full text is of this article is available at the Dhaka Univ. J. Pharm. Sci. website
 
Publisher Dhaka University
 
Date 2007-06-18
 
Type
 
Identifier http://www.banglajol.info/index.php/JPharma/article/view/207
 
Source Dhaka University Journal of Pharmaceutical Sciences; Vol 4, No 2 (2005)
 
Language en