[(2S,3S,5S,6R,8S,9R,10S,13R,14S,16R,17R)-2,3,16-triacetyloxy-17-[(2R)-6-acetyloxy-2-hydroxy-6-methyl-3-oxoheptan-2-yl]-6-hydroxy-4,4,9,13,14-pentamethyl-11-oxo-2,3,6,7,8,10,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-5-yl] 3-chlorobenzoate | 1424039-05-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: [(2S,3S,5S,6R,8S,9R,10S,13R,14S,16R,17R)-2,3,16-triacetyloxy-17-[(2R)-6-acetyloxy-2-hydroxy-6-methyl-3-oxoheptan-2-yl]-6-hydroxy-4,4,9,13,14-pentamethyl-11-oxo-2,3,6,7,8,10,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-5-yl] 3-chlorobenzoate
• CAS: 1424039-05-3
• 化学式: C₄₅H₆₁ClO₁₄
• 分子量: 861.424
• InChiKey: NHBNUKDVHLQFKN-IOODGOBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  60
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  206
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  葫芦素 IIA 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 [(2S,3S,5S,6R,8S,9R,10S,13R,14S,16R,17R)-2,3,16-triacetyloxy-17-[(2R)-6-acetyloxy-2-hydroxy-6-methyl-3-oxoheptan-2-yl]-6-hydroxy-4,4,9,13,14-pentamethyl-11-oxo-2,3,6,7,8,10,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-5-yl] 3-chlorobenzoate
  参考文献：
  名称：

  Synthesis of hemslecin A derivatives: A new class of hepatitis B virus inhibitors

  摘要：

  A series of hemslecin A derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities, namely, inhibiting the secretion of hepatitis B surface antigen (HBsAg), hepatitis B e antigen (HBeAg), and HBV DNA replication on HepG 2.2.15 cells. Most of the derivatives showed enhanced anti-HBV activities, of which compounds A1-A7, B5, C and E exhibited significant activities inhibiting HBV DNA replication with IC50 values of 2.8-11.6 mu M, comparable to that of the positive control, tenofovir. Compounds A1-A3, A5, B5, and C displayed low cytotoxicities, which resulted in high SI values of 89.7, 55.6, 77.8, >83.4, >55.8, and >150.5, respectively. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.024

文献信息

• Synthesis of hemslecin A derivatives: A new class of hepatitis B virus inhibitors
  作者：Rui-Hua Guo、Chang-An Geng、Xiao-Yan Huang、Yun-Bao Ma、Quan Zhang、Li-Jun Wang、Xue-Mei Zhang、Rong-Ping Zhang、Ji-Jun Chen

  DOI：10.1016/j.bmcl.2013.01.024

  日期：2013.3

  A series of hemslecin A derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities, namely, inhibiting the secretion of hepatitis B surface antigen (HBsAg), hepatitis B e antigen (HBeAg), and HBV DNA replication on HepG 2.2.15 cells. Most of the derivatives showed enhanced anti-HBV activities, of which compounds A1-A7, B5, C and E exhibited significant activities inhibiting HBV DNA replication with IC50 values of 2.8-11.6 mu M, comparable to that of the positive control, tenofovir. Compounds A1-A3, A5, B5, and C displayed low cytotoxicities, which resulted in high SI values of 89.7, 55.6, 77.8, >83.4, >55.8, and >150.5, respectively. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.