11,23,24,25-tetra-O-(3-methylbutanoyl)-alisol A | 1202531-21-2

• 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: 11,23,24,25-tetra-O-(3-methylbutanoyl)-alisol A
• 英文别名: [(5R,8S,9S,10S,11S,14R)-17-[(1R,3S,4R)-1,5-dimethyl-3,4,5-tris(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)-4,4,8,10,14-pentamethyl-17-[(2R,4S,5R)-6-methyl-4,5,6-tris(3-methylbutanoyloxy)heptan-2-yl]-3-oxo-1,2,5,6,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-11-yl] 3-methylbutanoate
• CAS: 1202531-21-2
• 化学式: C₅₀H₈₂O₉
• 分子量: 827.196
• InChiKey: GGDGBXMVCBFKRQ-MOOQEUAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  59
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 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66%的产率得到11,23,24,25-tetra-O-(3-methylbutanoyl)-alisol A
  参考文献：
  名称：

  Anti-HBV agents. Part 3: Preliminary structure–activity relationships of tetra-acylalisol A derivatives as potent hepatitis B virus inhibitors

  摘要：

  Thirty-two tetra-acylated derivatives of alisol A were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities and cytotoxicities in vitro. Among the series of alisol A derivatives examined, five analogues were active against HBV surface antigen (HBsAg) and HBV e antigen (HBeAg) secretion in HepG 2.2.15 cells. These results also provide interesting structure-activity relationships of tetra-acylalisol A derivatives. Compounds tetra-acetyl alisol A (A1), tetra-methoxyacetyl alisol A (A23), and tetra-ethoxyacetyl alisol A (A24) exhibited high activities against secretion of HBsAg with IC50 values of 0.0048, 0.0044, and 0.014 mM, respectively, HBeAg with IC50 values of 0.011, 0.012, and 0.018 mM, respectively, and remarkable selective index values SIHBsAg > 333, SIHBeAg > 145; SIHBsAg = 209, SIHBeAg = 77; and SIHBsAg > 200, SIHBeAg > 156, respectively. Additional studies in rats showed that compound A1 has favorable pharmacokinetic prosperities for further development purpose, with elimination half-time (t(1/2)) of 1.63 h and oral bioavailability (F) of 40.9%. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.006

文献信息

• Anti-HBV agents. Part 3: Preliminary structure–activity relationships of tetra-acylalisol A derivatives as potent hepatitis B virus inhibitors
  作者：Quan Zhang、Zhi-Yong Jiang、Jie Luo、Yun-Bao Ma、Ji-Feng Liu、Rui-Hua Guo、Xue-Mei Zhang、Jun Zhou、Wei Niu、Fei-Fei Du、Li Li、Chuan Li、Ji-Jun Chen

  DOI：10.1016/j.bmcl.2009.10.006

  日期：2009.12

  Thirty-two tetra-acylated derivatives of alisol A were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities and cytotoxicities in vitro. Among the series of alisol A derivatives examined, five analogues were active against HBV surface antigen (HBsAg) and HBV e antigen (HBeAg) secretion in HepG 2.2.15 cells. These results also provide interesting structure-activity relationships of tetra-acylalisol A derivatives. Compounds tetra-acetyl alisol A (A1), tetra-methoxyacetyl alisol A (A23), and tetra-ethoxyacetyl alisol A (A24) exhibited high activities against secretion of HBsAg with IC50 values of 0.0048, 0.0044, and 0.014 mM, respectively, HBeAg with IC50 values of 0.011, 0.012, and 0.018 mM, respectively, and remarkable selective index values SIHBsAg > 333, SIHBeAg > 145; SIHBsAg = 209, SIHBeAg = 77; and SIHBsAg > 200, SIHBeAg > 156, respectively. Additional studies in rats showed that compound A1 has favorable pharmacokinetic prosperities for further development purpose, with elimination half-time (t(1/2)) of 1.63 h and oral bioavailability (F) of 40.9%. (C) 2009 Elsevier Ltd. All rights reserved.