11,23,24-tri-O-3'-methylbutanoyl-alisol A | 1159410-09-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 11,23,24-tri-O-3'-methylbutanoyl-alisol A
• 英文别名: [(5R,8S,9S,10S,11S,14R)-17-[(1R,3S,4R)-5-hydroxy-1,5-dimethyl-3,4-bis(3-methylbutanoyloxy)hexyl]-4,4,8,10,14-pentamethyl-3-oxo-1,2,5,6,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-11-yl] 3-methylbutanoate；[(5R,8S,9S,10S,11S,14R)-17-[(2R,4S,5R)-6-hydroxy-6-methyl-4,5-bis(3-methylbutanoyloxy)heptan-2-yl]-4,4,8,10,14-pentamethyl-3-oxo-1,2,5,6,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-11-yl] 3-methylbutanoate
• CAS: 1159410-09-9
• 化学式: C₄₅H₇₄O₈
• 分子量: 743.078
• InChiKey: SGSODVBQTAECOK-PRSLQLEGSA-N

物化性质

• 沸点：
  722.9±60.0 °C(predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  53
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  11,23,24-tri-O-3'-methylbutanoyl-alisol A 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以78%的产率得到11,23,24-tri-O-3'-methylbutanoyl-25-anhydroalisol A
  参考文献：
  名称：

  Anti-HBV agents. Part 2: Synthesis and in vitro anti-hepatitis B virus activities of alisol A derivatives

  摘要：

  Chemical modi. cations were performed on hydroxyl groups at C-11,23,24,25 positions and C-13(17) double bond of alisol A for structure-activity relationship study. Forty-one derivatives of alisol A were synthesized and assayed for their in vitro anti-hepatitis B virus (HBV) activities and cytotoxicities. Of them, 14 compounds were active against HBV surface antigen (HBsAg) and HBV e antigen (HBeAg) secretion in HepG 2.2.15 cells, and the most promising compound 25 exhibited high activities against secretion of HBsAg (IC50 = 0.028 mM), HBeAg (IC50 = 0.027 mM) and remarkable selective indices (SIHBsAg > 90, SIHBeAg > 93). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.122
• 作为产物：
  描述：

  异戊酸 、 泽泻醇A 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到11,23,24-tri-O-3'-methylbutanoyl-alisol A
  参考文献：
  名称：

  Anti-HBV agents. Part 2: Synthesis and in vitro anti-hepatitis B virus activities of alisol A derivatives

  摘要：

  Chemical modi. cations were performed on hydroxyl groups at C-11,23,24,25 positions and C-13(17) double bond of alisol A for structure-activity relationship study. Forty-one derivatives of alisol A were synthesized and assayed for their in vitro anti-hepatitis B virus (HBV) activities and cytotoxicities. Of them, 14 compounds were active against HBV surface antigen (HBsAg) and HBV e antigen (HBeAg) secretion in HepG 2.2.15 cells, and the most promising compound 25 exhibited high activities against secretion of HBsAg (IC50 = 0.028 mM), HBeAg (IC50 = 0.027 mM) and remarkable selective indices (SIHBsAg > 90, SIHBeAg > 93). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.122

文献信息

• Anti-HBV agents. Part 2: Synthesis and in vitro anti-hepatitis B virus activities of alisol A derivatives
  作者：Quan Zhang、Zhi-Yong Jiang、Jie Luo、Ji-Feng Liu、Yun-Bao Ma、Rui-Hua Guo、Xue-Mei Zhang、Jun Zhou、Ji-Jun Chen

  DOI：10.1016/j.bmcl.2009.02.122

  日期：2009.4

  Chemical modi. cations were performed on hydroxyl groups at C-11,23,24,25 positions and C-13(17) double bond of alisol A for structure-activity relationship study. Forty-one derivatives of alisol A were synthesized and assayed for their in vitro anti-hepatitis B virus (HBV) activities and cytotoxicities. Of them, 14 compounds were active against HBV surface antigen (HBsAg) and HBV e antigen (HBeAg) secretion in HepG 2.2.15 cells, and the most promising compound 25 exhibited high activities against secretion of HBsAg (IC50 = 0.028 mM), HBeAg (IC50 = 0.027 mM) and remarkable selective indices (SIHBsAg > 90, SIHBeAg > 93). (C) 2009 Elsevier Ltd. All rights reserved.