Abstract

SYNTHESIS, CHARACTERIZATION & PHARMACOLOGICAL EVALUATION OF SOME NOVEL QUINOLINE DERIVATIVES

Rudra Pratap Singh*, Shivam Jaiswal, Shobhit Srivastava, Bhumika Yogi and Sujeet Kumar Gupta

ABSTRACT

A series of newer 2-((Z)-2-((5-chloro-3-methyl-1-(substituted)-1H-pyrazol-4-yl)methylene) hydrazinyl)quinoline-3-carbaldehyde (7a-e) derivatives was synthesized through acetanilide (1). In the first scheme, 2-chloro-3-formylquinoline (2) was prepared using acetanilide (1) by Vilsmeier-Haack reagent (DMF+POCl3).The 2-chloro-3-formylquinoline was further treated with hydrazine hydrate and ethanol which yield2-hydrazinylquinoline-3-carbaldehyde (3). In the second scheme,5-chloro-1-(substituted)-3-methyl-1H-pyrazole-4-carbaldehyde (6a-e) was synthesized through the reaction of substituted phenylhydrazine with ethylacetoacetate in the presence of diluted ethanol. In the third scheme, above synthesized compound 2-hydrazinylquinoline-3-carbaldehyde (3) and 5-chloro-1-(substituted)- 3-methyl-1H-pyrazole-4-carbaldehyde (6a-e) was again treated with Vilsmeier-Haack reagent (DMF + POCl3) to yield 2-((Z)-2-((5-chloro-3-methyl-1-(substituted)-1H-pyrazol-4-yl)methylene)hydrazinyl) quinoline-3-carbaldehyde (7a-e).Newer synthesized series have been confirmed on the basis of IR,1H NMR and Mass spectroscopy. All the synthesized compound was evaluated for their anti-inflammatory activities by using carrageenan induced rat paw edema model. It was found that compound 7a and 7e shows highest potency among all the synthesized derivatives whereas Diclofenac Sodium was taken as standard drug.

Keywords: Vilsmeier-Haack reaction, Quinoline, Anti-inflammatory, Carrageenan induced rat paw edema model.