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Molecules 2011, 16(4), 3410-3419; doi:10.3390/molecules16043410

Synthesis and Anticancer Activity of Some Novel Tetralin-6-yl-pyrazoline, 2-Thioxopyrimidine, 2-Oxopyridine, 2-Thioxo-pyridine and 2-Iminopyridine Derivatives

Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
Received: 7 March 2011 / Revised: 29 March 2011 / Accepted: 8 April 2011 / Published: 20 April 2011
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Abstract

The title compounds were prepared by reaction of 6-acetyltetralin (1) with different aromatic aldehydes 2a-c, namely 2,6-dichlorobenzaldehyde, 2,6-diflouro-benzaldehyde, and 3-ethoxy-4-hydroxybenzaldehyde, to yield the corresponding a,b-unsaturated ketones 3a-c. Compound 3b was reacted with hydrazine hydrate to yield the corresponding 2-pyrazoline 4, while compounds 3a,b reacted with thiourea to afford the 2-thioxopyrimidine derivatives 5a,b, respectively. The reaction of 1, and the aromatic aldehydes 2a-c with ethyl cyanoacetate, 2-cyano-thioacetamide or malononitrile in the presence of ammonium acetate yielded the corresponding 2-oxopyridines 6a,b, 2-thioxopyridines 7a-c or 2-iminopyridines 8a,b, respectively. The newly prepared compounds were evaluated for anticancer activity against two human tumor cell lines. Compound 3a showed the highest potency with IC50 = 3.5 and 4.5 μg/mL against a cervix carcinoma cell line (Hela) and breast carcinoma cell line (MCF7), respectively.
Keywords: tetrahydronaphthalenes; 2-pyrazoline; 2-thioxopyrimidine; 2-oxopyridine; 2-thioxopyridine; 2-iminipyridine; anticancer activity tetrahydronaphthalenes; 2-pyrazoline; 2-thioxopyrimidine; 2-oxopyridine; 2-thioxopyridine; 2-iminipyridine; anticancer activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Al-Abdullah, E.S. Synthesis and Anticancer Activity of Some Novel Tetralin-6-yl-pyrazoline, 2-Thioxopyrimidine, 2-Oxopyridine, 2-Thioxo-pyridine and 2-Iminopyridine Derivatives. Molecules 2011, 16, 3410-3419.

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