Synthesis and Investigation of Antimicrobial and Antioxidant Activity of 3-Nitro-N- (3-chloro-2-oxo-substituted-phenyl-azetidin-1-yl)naphtho [2,1-b]furan-2-carboxamides

K Shashikala Devi,D L Roopa,V P Vaidya,M Ramaiah

doi:10.1155/2010/863547

Abstract

Ethyl-3-nitronaphtho[2,1-b]furan-2-carboxylate(2)has been synthesized from ethyl naphtha [2,1-b]furan-2-carboxylate(1). This nitro product on reaction with hydrazine hydrate formed 3-nitronaphtho [2,1-b] furan-2-carbohydrazide(3). Various Schiff bases 3-nitro-N1(aryl-methylene)-substituted-naphtho [2,1-b]furan-2-carbohydrazides4(a-g)were obtained by treating hydrazide(3)with different aldehydes. These Schiff bases on reaction with chloro acetyl chloride in presence of triethylamine in dioxane yielded 3-nitro-N-(3-chloro-2-oxo-substituted-phenyl-azetidine-1-yl) naphtha [2,1-b]furan-2-carboxamides5(a-g). All the newly synthesized compounds have been characterized by spectral and analytical studies. The Schiff bases,4a-gand azetidione derivatives,5a-ghave been studied for antioxidant and antimicrobial activities.

Highlights

The 2-azetidinone (β-lactam) ring is the essential feature of a large number of biologically active compounds namely penicillins, cephalosporins, carumonam, aztreonam, thienamycine and the nocardicins[1]
The required starting materials, to accomplish the synthesis of title compounds, ethyl naphtho[2,1-b]furan-2-carboxylate (1) and ethyl 3-nitronaphtho[2,1-b]furan-2-carboxylate (2) were synthesised according to the procedure reported in the literature[16]
The reaction of ethyl 3- nitronaphtho[2,1-b]furan-2-carboxylate (2) with hydrazine hydrate in presence of acid catalyst in ethanol produced 3-nitronaphtho[2,1-b]furan-2-carbohydrazide (3)

Summary

Introduction

The 2-azetidinone (β-lactam) ring is the essential feature of a large number of biologically active compounds namely penicillins, cephalosporins, carumonam, aztreonam, thienamycine and the nocardicins[1]. The various naphtho[2,1-b]furan derivatives, synthesized in our laboratory have been shown to possess wide spectrum of biological and pharmacological activities[9,10,11,12]. There are several evidences that the presence of nitro group enhance the biological activities of the compounds many folds.

Results

Conclusion