New analogues of the antitumor alkaloid girolline: The 4-deazathiogirolline series

Aminothiazole analogues of the antitumor alkaloid girolline have been asymmetrically synthesised using the chiral pool. The key-steps involved the Hantzsch reaction to build the thiazole heterocycle and the functionalisation of the side chain using the triphenylphosphane chemistry (i.e. azidation-ch...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 1; pp. 97 - 101
Main Authors Nay, B, Schiavi, B, Ahond, A, Poupat, C, Potier, P
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 05.01.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
structure-activity relationships
antitumor
aminothiazole
CONFIGURATION
girolline
CLEAVAGE
DERIVATIVES
chiral pool
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Summary:Aminothiazole analogues of the antitumor alkaloid girolline have been asymmetrically synthesised using the chiral pool. The key-steps involved the Hantzsch reaction to build the thiazole heterocycle and the functionalisation of the side chain using the triphenylphosphane chemistry (i.e. azidation-chlorination of a diol). Biological activity of analogues has been evaluated (cytotoxicity on KB tumor cells and anti-HIV activity).
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2004-834907