873936-01-7Relevant articles and documents
Synthesis and structure-activity relationship of 3-O-acylated (-)-epigallocatechins as 5α-reductase inhibitors
Lin, Shu Fu,Lin, Yu-Hsiang,Lin, Mengju,Kao, Yi-Feng,Wang, Ru-Wen,Teng, Li-Wei,Chuang, Shih-Hsien,Chang, Jia-Ming,Yuan, Ta-Tung,Fu, Kuo Chu,Huang, Kuan Pin,Lee, Ying-Shuen,Chiang, Chao-Cheng,Yang, Sheng-Chuan,Lai, Chun-Liang,Liao, Chu-Bin,Chen, Paonien,Lin, Young-Sun,Lai, Kuei-Tai,Huang, Hung-Jyun,Yang, Ju-Ying,Liu, Chia-Wei,Wei, Win-Yin,Chen, Chi-Kuan,Hiipakka, Richard A.,Liao, Shutsung,Huang, Jiann-Jyh
experimental part, p. 6068 - 6076 (2011/01/13)
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.
