[(2S,3S,8S,9R,10R,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-3,16-bis[(2-ethoxyacetyl)oxy]-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-2-yl] 2-ethoxyacetate | 1424039-14-4

• 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,8S,9R,10R,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-3,16-bis[(2-ethoxyacetyl)oxy]-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-2-yl] 2-ethoxyacetate
• CAS: 1424039-14-4
• 化学式: C₄₂H₆₆O₁₃
• 分子量: 778.978
• InChiKey: WLHHEEAKGHZNFA-KWSOANICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  55
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  181
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  乙氧基乙酸 、 雪胆素乙 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80%的产率得到[(2S,3S,8S,9R,10R,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-3,16-bis[(2-ethoxyacetyl)oxy]-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-2-yl] 2-ethoxyacetate
  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.