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Semi-synthesis and antitumor activity of 6-isomers of 5, 8-O-dimethyl acylshikonin derivatives.

Abstract：

:We recently discovered that 5, 8-O-dimethyl acylshikonin derivatives displayed the selectivity towards MCF-7 and no toxicity to normal cells. Herein, a series of the corresponding 6-isomers of 5, 8-O-dimethyl acylshikonin derivatives were synthesized starting from shikonin. In vitro evidence of the cytotoxicities indicated that most of thecompounds were more active than or comparative to shikonin and retained the selectivity against MCF-7, MDA-MB-231 besides no toxicity in the normal cells. Also, in vivo anticancer activity of the positional isomers 5p, 6c further showed that 6-isomers of 5, 8-O-dimethyl acylshikonin derivatives were more active than their corresponding 2-isomers. Thus, we may conclude that the position of the side chain of shikonin attached to 5,8-dimethoxy -1,4-naphthoquinone is associated with the antitumor activity.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Zhou W,Zhang X,Xiao L,Ding J,Liu QH,Li SS

doi

10.1016/j.ejmech.2011.05.006

subject

Has Abstract

pub_date

2011-08-01 00:00:00

pages

3420-7

issue

8

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(11)00368-0

journal_volume

46

pub_type

杂志文章

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