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Facile Synthesis of 7‐ epi ‐Taxane and Its Derivatives and Preliminary Evaluation of Anticancer Activity
Author(s) -
Li Zhao,
Feng Jia,
Zou Kun,
Yang Zhuo,
Zhang Yong,
Xu Zhijian,
Li Bo,
Shi Jiye,
Li Yiming,
Zhu Weiliang,
Chen Kaixian
Publication year - 2016
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201600381
Subject(s) - taxane , chemistry , docetaxel , paclitaxel , du145 , catalysis , epimer , solvent , stereochemistry , organic chemistry , prostate cancer , cancer , lncap , medicine , breast cancer
7‐ epi ‐Taxane has been achieved efficiently in gram scale from natural taxane via inversion of the 7‐hydroxyl group simply using Ag 2 O as catalyst and DMF as solvent. The catalyst could be quantitatively recovered by filtration without loss of catalytic activity. This condition is also applicable to the direct epimerization of taxane derivatives ( e.g. , docetaxel and paclitaxel) to 7‐ epi‐ taxane derivatives ( e.g ., 7‐ epi ‐docetaxel and 7‐ epi ‐paclitaxel). Furthermore, 33 ester derivatives of 7‐ epi ‐taxane with different amino acid moieties at the position of C‐13 were successfully synthesized via esterification without protecting C‐7‐OH. Bioassay results revealed that compounds 13 and 18 have good selectivity against prostatic cancer cell line DU145, with IC 50 value as low as 15.9 nmol/L for 18 .