(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl dodecanoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl dodecanoate
• 英文别名: 3-O-dodecanoyl-(-)-epigallocatechin；[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] dodecanoate
• 化学式: C₂₇H₃₆O₈
• 分子量: 488.578
• InChiKey: AFZMDYLYISIZCL-SHQCIBLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  [(2R,3R)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]phenyl]-3,4-dihydro-2H-chromen-3-yl] dodecanoate 在 氢氟酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl dodecanoate
  参考文献：
  名称：

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

  摘要：

  A series of 3-O-acylated (-)-epigallocatechins were synthesized and their inhibition of steroid 5 alpha-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 mu M, which was similar to 12-fold more potent than EGCG (IC50 = 6.29 mu M). Introduction of monounsaturated fatty acid provided the most potent compound 6 (IC50 = 0.48 mu M), which showed moderate anti-tumor activity in vivo. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.10.011

文献信息

• Antitumor promoting activities of 3-O-acyl-(−)-epigallocatechins
  作者：Shinichi Uesato、Yutaka Kitagawa、Yukihiko Hara、Harukuni Tokuda、Masato Okuda、Xiao Yang Mou、Teruo Mukainaka、Hoyoku Nishino

  DOI：10.1016/s0960-894x(00)00314-0

  日期：2000.8

  As an exploratory investigation of antitumor promoting compounds, 3-O-acyl-(-)-epigallocatechins possessing a straight-, branched-, phenyl-inserted- or 1,4-phenylene-inserted-acyl chain of varying length from C-4 to C-18 were synthesized and evaluated their inhibitory effects against the activation of the Epstein-Barr virus early antigen (EBV-EA). It was indicated that the epigallocatechin derivatives having the straight- or branchcd-acyl chain of C-8 to C-11 carbon atoms achieve marked effects. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Tumor chemopreventive activity of 3- O -acylated (−)-epigallocatechins
  作者：Ayako Kumagai、Yasuo Nagaoka、Tomoko Obayashi、Yasuhiro Terashima、Harukuni Tokuda、Yukihiko Hara、Teruo Mukainaka、Hoyoku Nishino、Hiroshi Kuwajima、Shinichi Uesato

  DOI：10.1016/j.bmc.2003.08.016

  日期：2003.11

  In order to seek promising cancer chemopreventive agents, we assessed the antitumor promoting activities of 3-O-octanoyl or 3-O-(2-methyloctanoyl)-(-)-epigallocatechins, inhibiting markedly the activation of Epstein-Barr virus early antigen, in a two-stage mouse skin carcinogenesis assay. As a result, these derivatives inhibited a papilloma formation 1.3-1.6-fold more strongly than (-)-epigallocatechin gallate well established as anti-tumor promoter. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis and structure–activity relationship of 3-O-acylated (–)-epigallocatechins as 5α-reductase inhibitors
  作者：Shu Fu Lin、Yu-Hsiang Lin、Mengju Lin、Yi-Feng Kao、Ru-Wen Wang、Li-Wei Teng、Shih-Hsien Chuang、Jia-Ming Chang、Ta-Tung Yuan、Kuo Chu Fu、Kuan Pin Huang、Ying-Shuen Lee、Chao-Cheng Chiang、Sheng-Chuan Yang、Chun-Liang Lai、Chu-Bin Liao、Paonien Chen、Young-Sun Lin、Kuei-Tai Lai、Hung-Jyun Huang、Ju-Ying Yang、Chia-Wei Liu、Win-Yin Wei、Chi-Kuan Chen、Richard A. Hiipakka、Shutsung Liao、Jiann-Jyh Huang

  DOI：10.1016/j.ejmech.2010.10.011

  日期：2010.12

  A series of 3-O-acylated (-)-epigallocatechins were synthesized and their inhibition of steroid 5 alpha-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 mu M, which was similar to 12-fold more potent than EGCG (IC50 = 6.29 mu M). Introduction of monounsaturated fatty acid provided the most potent compound 6 (IC50 = 0.48 mu M), which showed moderate anti-tumor activity in vivo. (C) 2010 Elsevier Masson SAS. All rights reserved.