N-Substituted-3-chloro-2-azetidinones: Synthesis and characterization of new novel anti-inflammatory agents
Journal Title: Journal of Pharmaceutical Sciences and Research - Year 2009, Vol 1, Issue 2
Abstract
Various substituted 4-(m-hydroxy-p-methoxy phenyl)-1-[(6'-fluoro-7'-substituted (1,3)-benzothiazol-2'-yl) amido-2- phenyl]-3-chloro azetidin–2–one containing different functional groups have been synthesized by treating fluorochloroaniline with KSCN in presence of bromine in glacial acetic acid and ammonia to get 2-amino-6-fluoro- 7-chloro-(1,3)-benzothiazole, which was treated with anthranillic acid in presence of dry pyridine to get 2-amino-N- (6-fluoro-7-chloro-(1,3)-benzothiazol-2-yl) benzamide. To the above, refluxed with vanillin and alcohol in presence of Conc.HCl to get 2-(3-hydroxy-4-methoxy benzylidene amino phenyl amido)-6-fluoro-7-chloro-(1, 3)- benzothiazole or Schiff’s base. A Solution of Schiff’s base in 1,4-dioxane was added to well-stirred mixture of chloroacetyl chloride and triethylamine to get Azetidinone. To the above product different primary and secondary aromatic amines in presence of DMF were treated to get newly targeted compound through replacing at 7th position chlorine. The lead compounds were characterized by melting point, TLC, calculated elemental analysis, UV, IR and 1H NMR spectral studies. The compounds were tested for anti-inflammatory activity (in-vitro) by protein denaturation method and showed significant activity at low and high concentration compared to standard; still further studies are requested.
Authors and Affiliations
Vijay Kumar M. M. J. , Nagaraja T. S, Shameer H, Jayachandran E, Sreenivasa G. M.
Keywords
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