Heterocyclic Synthesis via Enaminones: Synthesis and Molecular Docking Studies of Some Novel Heterocyclic Compounds Containing Sulfonamide Moiety

Ahmed Abd El-Hameed Hassan

doi:10.4236/ijoc.2014.41009

Abstract

4-Acetyl-N, N-diethylbenzenesulfonamide (1) was condensed with dimethylformamide dimethy-lacetal (DMF-DMA) to yield the enaminone, which reacts readily with different reagents to give the corresponding pyrazoles, triazolopyrimidine, imidazopyridine, pyrimidopyrimidine, pyrazolopyrimidine, benzofuran, pyranone, pyridine, pyrimidine and pyrazolopyridazine derivatives. These compounds were designed to comply with the general features of sulfonamide pharmacophore which act as Cyclooxygenase (COX-2) inhibitors. Virtual screening using molecular docking studies of the synthesized compounds was performed by (MOE), the molecular docking results indicate that, some synthesized compounds suitable inhibitor against (COX-2) with further modification.

Highlights

Enaminones are polydentate reagents that have been utilized extensively in this decade as building blocks in organic synthesis [1]-[6]
We have reported a variety of syntheses of heteroaromatics developed using functionally substituted enaminones as readily obtainable building blocks possessing multiple electrophilic and nucleophilic moieties
The structure of the enaminone 2 was confirmed on the basis of elemental analysis and spectral data

Summary

Introduction

Enaminones are polydentate reagents that have been utilized extensively in this decade as building blocks in organic synthesis [1]-[6]. Diclofenac is a one from famous available members of this drug’s class under current clinical usage [17], and suffers from a common toxicity of gastrointestinal drawback, due to inhibition non-selectivity of cyclooxygenase enzyme [18]-[20], its display anti-microbial [21]-[23], ulcerogenic, analgesic, anti-inflammatory, lipid peroxidation [24] [25], antitumor [26] and inhibitor formation of transthyretin amyloid fibril properties [27]. We have reported a variety of syntheses of heteroaromatics developed using functionally substituted enaminones as readily obtainable building blocks possessing multiple electrophilic and nucleophilic moieties

Experimental

Molecular Modeling Study

Stepwise Docking Method MOE Stepwise

Chemistry

H2N NH2

Docking Studies