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Molecules 2011, 16(1), 52-73; doi:10.3390/molecules16010052

Novel Synthesis and Antitumor Evaluation of Polyfunctionally Substituted Heterocyclic Compounds Derived from 2-Cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide

Department of Chemistry, Faculty of Science, Helwan University, Ain Helwan, Cairo, Egypt
Department of Organic Chemistry, Faculty of Pharmacy, October University for Modern Sciences and Arts, October City, Egypt
Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt
Author to whom correspondence should be addressed.
Received: 10 November 2010 / Revised: 20 December 2010 / Accepted: 22 December 2010 / Published: 27 December 2010
(This article belongs to the Section Medicinal Chemistry)
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The reaction of 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene with ethyl cyanoacetate gave 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide. The latter was used to synthesize different heterocyclic derivatives comprising thiophene, thiazole, pyrazole, pyridine, pyrimidine, and coumarin rings. The mechanistic and synthetic pathways depended on regioselective attack and/or cyclization by the cyanoacetamido moiety in the key precursor on various chemical reagents. The competition of the reaction pathways including dipolar cyclization, dinucleophilic-bielectrophilic attack, β-attack, Gewald-type attack, and condensation reactions led to the diversity of the synthesized products. The antitumor activities of the synthesized products were studied and evaluated. Most of the compounds revealed high inhibitory effects when screened in vitro for their antiproliferative activity. Three human cancer cell lines, namely, breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) were used in the screening tests. The simplicity of the synthetic procedures which mainly involved one-pot reactions under mild reaction conditions, the convenience of yield production and the diversity of the reactive sites in the produced systems play a valuable role for further heterocyclic transformations and further biological investigations.
Keywords: 4,5,6,7-tetrahydrobenzo[b]thiophene; thiazole; pyrazole; pyridine; antitumor 4,5,6,7-tetrahydrobenzo[b]thiophene; thiazole; pyrazole; pyridine; antitumor

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Shams, H.Z.; Mohareb, R.M.; Helal, M.H.; Mahmoud, A.E. Novel Synthesis and Antitumor Evaluation of Polyfunctionally Substituted Heterocyclic Compounds Derived from 2-Cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide. Molecules 2011, 16, 52-73.

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