Volume 32, Issue 18
Preparative Organic Chemistry
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ChemInform Abstract: Synthesis and Cytotoxic Activity of a Series of Diacetylenic Compounds Related to Falcarindiol.

William N. Setzer

William N. Setzer

Dep. Chem., Univ. Ala., Huntsville, AL 35899, USA

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Xuyuan Gu

Xuyuan Gu

Dep. Chem., Univ. Ala., Huntsville, AL 35899, USA

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Eric B. Wells

Eric B. Wells

Dep. Chem., Univ. Ala., Huntsville, AL 35899, USA

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Mary C. Setzer

Mary C. Setzer

Dep. Chem., Univ. Ala., Huntsville, AL 35899, USA

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Debra M. Moriarity

Debra M. Moriarity

Dep. Chem., Univ. Ala., Huntsville, AL 35899, USA

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First published: 27 May 2010

Abstract

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ChemInform Abstract

Unsymmetrical diacetylenes (VI) and (VII) are synthesized by modification of the Cadiot—Chodkiewicz coupling reaction of alkynyl bromides (IV) with terminal alkynes. Symmetrical diacetylenes (VIII) and (X) are obtained by using the corresponding alkynyl bromides or by using the Zal′kind modification of the Glaser coupling [(IX)→(X)]. The diacetylenes are tested for in vitro cytotoxic activity against human hepatocellular carcinoma and rat hepatoma cell lines. Compounds (VIc) and (VII) are the most active ones, while symmetrical diacetylenes (VIIIb) and (VIIIc) show intermediate cytotoxicities.

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