Jacobs Journal of Organic Chemistry

Synthesis of Pyran, Pyridine, Thiophene, Pyrimidine and Thiazole Derivatives with Antitumor Activities

*Rafat M. Mohareb
Department Of Chemistry, Cairo University, Giza, Egypt

*Corresponding Author:
Rafat M. Mohareb
Department Of Chemistry, Cairo University, Giza, Egypt
Email:raafat_mohareb@yahoo.com

Published on: 2017-02-16

Abstract

The aim of present study was the uses of 4- methyl cyanoacetanilide (1) in the synthesis of pyridine, pyran, thiophene, thiazole, pyrimidine, chromen derivatives together with their antitumor evaluations. The work has resulted in the synthesis of a variety of 2- aminopyran, 2- hydroxypyran, 2-amino pyridine, 2-hydroxypyridine, 4,5,6,7-tetrahydrobenzo[b]thiophene, N-benzal,N-acetyl, N-phenylthiourea, thiazole, pyrimidine, phenylhydrazone, benzalydine, ethoxyethine and N- phenylmethino derivatives. The antitumor activities of the newly synthesized product were evaluated against cancer.

Keywords

Pyridine; Pyran; Thiophene; Pyrimidine; Antitumor Activities

Introduction

Multicomponent reactions (MCRs) have emerged as a valuable tool in the preparation of structurally diverse chemical libraries of heterocyclic compounds [1]. They are inherently atom
economical processes in which relatively complex products can be obtained in a one-pot reaction from simple starting materials, and thus they exemplify many of the desired features
of an ideal synthesis. MCRs are generally much more environmentally friendly and offer access to large compound libraries with diverse functionalities with the avoidance of protection
and deprotection steps for possible combinatorial surveying of structural variations. In view of the increasing interest in the preparation of a large variety of heterocyclic compound libraries, the development of new synthetically valuable MCRs with several diversity points remains a challenge for both academic and industrial institutions [2]. Thiophene and its derivatives are an important class of heterocyclic compounds possessing broad biological activities, such as anti-inflammatory [3], analgesic [3], antioxidant [4], antitubercular [5], antidepressant [6], sedative [6], antiamoebic [7], oral analgesic [8], anti-metabolite [9] and antineoplastic properties [10]. From the aforementioned reports, it seemed that the development of an efficient, rapid, and clean synthetic route towards focused libraries of such compounds is of great importance to both medicinal and synthetic chemists. Hence in this paper, we report a one-pot, three-component reaction for the synthesis of pyran derivatives through the reaction of α-cyano-4-methylacetanilide (1) with cyanomethylene derivatives and aromatic aldehydes. All the synthesized compounds were characterized using FT-IR, 1H NMR, 13C NMR, and mass spectrometry and were subjected to screening towards cancer cell lines.