Anticancer, anti-inflammatory, and analgesic activities of synthesized 2-(substituted phenoxy) acetamide derivatives.

Rahul Rama Hegde,Dilipkumar Pal,Priyanka Rani,Syed Riaz Hashim

doi:10.1155/2014/386473

Abstract

The aphorism was to develop new chemical entities as potential anticancer, anti-inflammatory, and analgesic agents. The Leuckart synthetic pathway was utilized in development of novel series of 2-(substituted phenoxy)-N-(1-phenylethyl)acetamide derivatives. The compounds containing 1-phenylethylamine as basic moiety attached to substituted phenols were assessed for their anticancer activity against MCF-7 (breast cancer), SK-N-SH (neuroblastoma), anti-inflammatory activity, and analgesic activity. These investigations revealed that synthesized products 3a–j with halogens on the aromatic ring favors as the anticancer and anti-inflammatory activity. Among all, compound 3c N-(1-(4-chlorophenyl)ethyl)-2-(4-nitrophenoxy)acetamide exhibited anticancer, anti-inflammatory, and analgesic activities. In conclusion, 3c may have potential to be developed into a therapeutic agent.

Highlights

In the past decade, numerous advances have taken place in the understanding of pathogenesis of cancer and its relationship with inflammation
Large scale of studies indicates that overexpression of COX2 strongly appeared in human breast carcinomas approximately 40% and in colorectal carcinomas approximately 60%
COX-2 is found during overexpression of human epidermal growth factor receptor 2 (HER2/neu)

Summary

Introduction

Numerous advances have taken place in the understanding of pathogenesis of cancer and its relationship with inflammation. Apart from the aliphatic compounds, 1,4-benzodiazepines were synthesized by the Leuckart Wallach reaction containing the benzodiazepine scaffold and were originated with various biological activities (benzodiazepine family) comprised mainly of central nervous system (CNS) suppressant due to its anxiolytic, anticonvulsant, sedative, and muscle relaxant activities It is used in various marketed drugs such as alprazolam, bromazepam, chlorazepate, and valium [11]. Compounds with 2-phenoxy-Nphenylacetamide core nucleus as in Figure 1 (1a and 1b) have shown remarkable research and demonstrated a variety of biological activities such as antimycobacterial [16], antiparasitic [17], antiviral [18], and anticancer [19]activities [20,21,22,23] These compounds are reported with inhibition of Pgp efflux transporters which are beneficial in the treatment of multidrug resistant strains of cancer cells. We report structure activity relationships and biological assessment of the titled compounds

Experiment

Synthesis

Pharmacological Screening

C17 H18 N2 O4

Results and Discussion

C NHCOCH2Cl H