Jacobs Journal of Organic Chemistry

New Approaches for the Synthesis of Thiophenes, Thiazole, Pyran Derivatives, and their Antitumor Evaluation

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

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

Published on: 2017-11-01


This research aims to a novel synthesis of thiophene, pyrans, azoles and azines derivatives in which we started with cyclopentanone as starting material which reacted with malononitrile and ethyl cyanoacetate. The synthesized compounds were confirmed by spectral and analytical data. The biological evaluation of compounds are tested on three different tumor cell lines such as breast adenocarcinoma, CNS cancer, and non-small lung cancer and was compared to the inhibitory effect of Doxorubicin. And the results revealed that compounds 7, 13b and 17b have the highest inhibitory effect.


Thiophene; Pyrazole; Pyrane; Pyridine; Cytotoxicity


Multi-component reactions have been proved as an important tool for the syntheses of many multi-substituted heterocyclic ring-containing compounds [1]. Synthesis of different substituted 4H-pyrans has been studied in the literature [2-5]. Pyrans and their derivatives are of considerable interest because of their wide range of biological property [6], such as spasmolytic, diuretic, anti-coagulant, anti-cancer, anti anaphylactic activity [7–11]. In addition, they can be used as cognitive enhancers, for the treatment of neurodegenerative disease, including Alzheimer’s disease, amyotrophic lateral sclerosis, Huntington’s disease, Parkinson’s disease, AIDS-associated dementia and Down’s syndrome as well as for the treatment of schizophrenia and myoclonus [12]. 4H-Pyrans also constitute the structural unit of a series of natural products [13,14]. On the other hand, several synthetic routes for polyfunctional fused or pendant pyridine systems have been reported in the literature. They mainly involve intramolecular cyclization [15,16] multi-component intermolecular cyclization [17] metal-assisted coupling [18] microwave-assisted coupling [19,20] or cycloaddition [21], azo electronic coupling [22], regioselective hetero Diels-Alder [23] and internal Mannich reaction [24]. They have been used in a wide variety of biological applications [25]. For the mentioned biological values of both pyran and pyridine derivatives we demonstrate here the synthesis of a series of such compounds through the one pot multi-component reaction of cyclopentanone with aromatic aldehydes and either of malononitrile or ethyl cyanoacetate together with studying of the antitumor activity of these compounds.