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Synthesis, cytotoxic activity, and SAR analysis of the derivatives of taxchinin A and brevifoliol.

Abstract：

:Twenty-one derivatives of taxchinin A (1) and brevifoliol (2) were synthesized and evaluated for cytotoxicity against human non-small lung cancer (A549) cell line. Nine derivatives showed potent activity with IC(50) values from 0.48 to 6.22microM. 5-Oxo-13-TBDMS-taxchinin A (11) and 5-oxo-13,15-epoxy-13-epi-taxchinin A (15) are the most potent derivatives, with IC(50) at 0.48 and 0.75microM, respectively. The structure-activity relationship (SAR) of these compounds established that exocyclic unsaturated ketone at ring C is the key structural element for the activity, while the alpha,beta-unsaturated ketone positioned at ring A has no effect for the activity. The significant cytotoxicity of derivatives 11 and 15 may be due to the conformational change in the taxane rings. The 3D-QSAR study was conducted on this series of compounds, which provided optimal predictive comparative molecular field (CoMFA) model with cross-validated r(2) (q(2)) value of 0.64.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Zhao Y,Guo N,Lou LG,Cong YW,Peng LY,Zhao QS

doi

10.1016/j.bmc.2008.03.041

subject

Has Abstract

pub_date

2008-05-01 00:00:00

pages

4860-71

issue

9

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(08)00266-6

journal_volume

16

pub_type

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