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Synthesis of Novel 2‐O,3′‐N‐Linked Macrocyclic Taxoids with Variable Ring Size
Author(s) -
Querolle Olivier,
Dubois Joëlle,
Thoret Sylviane,
Dupont Christophe,
Guéritte Françoise,
Guénard Daniel
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390092
Subject(s) - chemistry , ring (chemistry) , stereochemistry , ring size , docetaxel , organic chemistry , medicine , surgery , chemotherapy
A series of macrocyclic taxoids was prepared by connecting the 2‐OH and 3′‐NH moieties with aliphatic chains to mimic the docetaxel solid‐state conformation. The synthesis was achieved by acylation of both positions with various bromoalkanoic acids, and ring closure was carried out with sodium sulfide. Nine 19‐ to 27‐membered macrocyclic taxoids were obtained and evaluated as inhibitors of microtubule disassembly as well as for their cytoxicity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)