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|Title:||Synthesis of dimeric and tetrameric macrolactams with cytotoxic activity||Authors:||Gentile, Gabriella
Fusar Bassini, Domenico
|Issue Date:||2000||Project:||None||Journal:||CANADIAN JOURNAL OF CHEMISTRY||Abstract:||
Cyclization of amino acid prepd. from 4,4-dimethylcyclohex-2-en-1-one by std. chem., yielded the dimeric and tetrameric macrolactams (I) and (II), resp., representing the first examples of "taxoid-like" compds. with heterocyclic B rings. I and II exhibited moderate antiproliferative activity in an in vitro cytotoxicity assay. Consequently, an orthogonally diprotected, dimeric macrolactam (III) (R = Me3CMe2Si) was synthesized and, after selective deprotection of the hydroxy group, was coupled with the docetaxel side chain to give the final compd. III [R = (S,R)-PhCH(NHCO2CMe3)CH(OH)CO] (IV), showing three-dimensional shape similarity to paclitaxel. Contrary to our expectations, IV proved to be as active as the parent compd. I. The structure of I has been confirmed by X-ray crystallog. anal. and is also reported.
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