Abstract
A simple synthesis of 1,2-dithiolan-3-ones from alpha,beta-unsaturated thiophenyl esters is reported. Introduction of the biologically active 1,2-dithiolan-3-one-1-oxide moiety of leinamycin into aldehydo-d-arabinose 11, the uridine derivative 16, and the deoxythymidine 21 was established. An extended bioactive part of leinamycin carrying a carbon-carbon triple bond was also synthesized. All of these analogues of leinamycin showed cytotoxic activity against HeLa3 tumor cells. Interestingly, the lipophilic, silyl group-containing derivatives proved to be more active than the hydrophilic counterparts.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antibiotics, Antineoplastic / chemical synthesis*
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Antibiotics, Antineoplastic / chemistry
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Antibiotics, Antineoplastic / pharmacology
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Drug Screening Assays, Antitumor
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HeLa Cells
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Humans
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Lactams / chemical synthesis*
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Lactams / chemistry
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Lactams / pharmacology
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Macrolides / chemical synthesis*
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Macrolides / chemistry
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Macrolides / pharmacology
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Structure-Activity Relationship
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Thiazoles / chemical synthesis*
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Thiazoles / chemistry
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Thiazoles / pharmacology
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Thiones / chemical synthesis*
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Thiones / chemistry
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Thiones / pharmacology
Substances
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Antibiotics, Antineoplastic
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Lactams
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Macrolides
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Thiazoles
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Thiones
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leinamycin