当前位置： SCI文献检索 > EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY期刊下所有文献 > Synthesis and structure-activity relationship of 3-O-acylated (-)-epigallocatechins as 5α-reductase inhibitors.

Synthesis and structure-activity relationship of 3-O-acylated (-)-epigallocatechins as 5α-reductase inhibitors.

Abstract：

:A series of 3-O-acylated (-)-epigallocatechins were synthesized and their inhibition of steroid 5α-reductase was studied. They were prepared from the reaction of EGCG with tert-butyldimethylsilyl chloride followed by reductive cleavage of the ester bond. The resultant (-)-epigallocatechins penta-O-tert-butyldimethylsilyl ether was esterified with different fatty acids then desilylated to provide the corresponding products. The activity of 3-O-acylated (-)-epigallocatechins increased with the increasing carbon numbers of the fatty acid moiety, reaching maximum for 16 carbon atoms (compound 4h) with an IC50 of 0.53 μM, which was ∼12-fold more potent than EGCG (IC50=6.29 μM). Introduction of monounsaturated fatty acid provided the most potent compound 6 (IC50=0.48 μM), which showed moderate anti-tumor activity in vivo.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Lin SF,Lin YH,Lin M,Kao YF,Wang RW,Teng LW,Chuang SH,Chang JM,Yuan TT,Fu KC,Huang KP,Lee YS,Chiang CC,Yang SC,Lai CL,Liao CB,Chen P,Lin YS,Lai KT,Huang HJ,Yang JY,Liu CW,Wei WY,Chen CK,Hiipakka RA,Liao S

doi

10.1016/j.ejmech.2010.10.011

subject

Has Abstract

pub_date

2010-12-01 00:00:00

pages

6068-76

issue

12

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(10)00751-8

journal_volume

45

pub_type

杂志文章

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