Abstract
A stereoselective and efficient method for free radical addition of benzyl thiol to aryl acetylene in the presence of Et3B-hexane has been developed for the synthesis of (Z) and (E)-styryl benzyl sulfides where base catalyzed hydrothiolations have failed. The scope of this reaction was successfully extended for the synthesis of (E)-ON 01910·Na, a phase III clinical stage anti-cancer agent and its inactive geometrical isomer (Z)-ON 01910·Na. It is interesting to note that all the E-isomers synthesized have shown better cytotoxicity profile on cancer cells compared to the Z-isomers.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkynes / chemical synthesis
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Alkynes / chemistry
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Alkynes / pharmacology*
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology*
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Cell Line, Tumor
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Cell Survival / drug effects
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Clinical Trials, Phase III as Topic
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Dose-Response Relationship, Drug
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Drug Screening Assays, Antitumor
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Glycine / analogs & derivatives*
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Glycine / chemical synthesis
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Glycine / chemistry
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Glycine / pharmacology
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Humans
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K562 Cells
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Molecular Structure
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Stereoisomerism
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Structure-Activity Relationship
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Sulfhydryl Compounds / chemistry*
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Sulfones / chemical synthesis
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Sulfones / chemistry
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Sulfones / pharmacology*
Substances
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Alkynes
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Antineoplastic Agents
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Sulfhydryl Compounds
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Sulfones
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ON 01910
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Glycine