triacetylalisol A | 19885-11-1

• 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: triacetylalisol A
• 英文别名: Alisol A-triacetate；11,23,24-tri-O-acetyl-alisol A；[(5R,8S,9S,10S,11S,14R)-17-[(1R,3S,4R)-3,4-diacetoxy-5-hydroxy-1,5-dimethyl-hexyl]-4,4,8,10,14-pentamethyl-3-oxo-1,2,5,6,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-11-yl] acetate；[(5R,8S,9S,10S,11S,14R)-17-[(2R,4S,5R)-4,5-diacetyloxy-6-hydroxy-6-methylheptan-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] acetate
• CAS: 19885-11-1
• 化学式: C₃₆H₅₆O₈
• 分子量: 616.836
• InChiKey: GKZNLEHHMNLAQH-SGNKRXEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  triacetylalisol A 在 palladium on activated charcoal 吡啶 、 氯化亚砜 、 氢气 作用下， 以 甲醇 为溶剂， 生成 25-Deoxy-alisol A-triacetate
  参考文献：
  名称：

  Murata,T. et al., Chemical and pharmaceutical bulletin, 1970, vol. 18, # 7, p. 1369 - 1384

  摘要：

  DOI：
• 作为产物：
  描述：

  Dihydroalisol A-triacetat 在 吡啶 、 chromium(VI) oxide 作用下， 生成 triacetylalisol A
  参考文献：
  名称：

  Murata,T.; Miyamoto,M., Chemical and pharmaceutical bulletin, 1970, vol. 18, p. 1354 - 1361

  摘要：

  DOI：

文献信息

• Anti-HBV agents. Part 1: Synthesis of alisol A derivatives: A new class of hepatitis B virus inhibitors
  作者：Quan Zhang、Zhi-Yong Jiang、Jie Luo、Pi Cheng、Yun-Bao Ma、Xue-Mei Zhang、Feng-Xue Zhang、Jun Zhou、Ji-Jun Chen

  DOI：10.1016/j.bmcl.2008.07.012

  日期：2008.8

  A series of alisol A derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities and cytotoxicities in vitro. The preliminary investigation demonstrates that simple modifications of the parent structure of alisol A can produce a number of potentially important derivatives against HBV. The most active anti-HBV compound 6a showed high activities against the secretion

  合成了一系列alisol A衍生物，并对其抗乙型肝炎病毒（HBV）活性和体外细胞毒性进行了评估。初步研究表明，简单修饰alisol A的母体结构可以产生许多潜在的抗HBV重要衍生物。最具活性的抗HBV化合物6a对HBV表面抗原（IC（50）= 0.024 mM），HBV e抗原（IC（50）= 0.028 mM）的分泌具有很高的活性，并且具有显着的选择性指数（SI（HBsAg）> 108，SI（HBeAg）> 93），被选作新型HBV抑制剂作进一步评估。
• Crude Drugs from Aquatic Plants. I. On the Constituents of Alismatis Rhizoma. (1). Absolute Stereostructures of Alisols E 23-Acetate, F, and G, Three New Protostane-Type Triterpenes from Chinese Alismatis Rhizoma.
  作者：Masayuki YOSHIKAWA、Shoko HATAKEYAMA、Nobumitsu TANAKA、Youichi FUKUDA、Johji YAMAHARA、Nobutoshi MURAKAMI

  DOI：10.1248/cpb.41.1948

  日期：——

  From the less polar fraction of Chinese Alismatis Rhizoma [the dried rhizome of the aquatic plant Alisma orientale JUZEP. collected in Szechwan Province, China (Sentaku in Japanese)], three new protostane-type triterpenes named alisols E 23-acetate, F, and G were isolated together with four guaiane-type sesquiterpenes and several known triterpenes including 13, 17-epoxyalisol A. The absolute stereostructures of alisols E 23-acetate, F, and G have been determined on the basis of chemical and physicochemical evidence, which included the chemical correlations of alisols E 23-acetate, F, and G with the known triterpenes alisols A and A 24-acetate, and the application of the modified Mosher's method.

  从中国泽泻根茎（中国四川省采集的水生植物东方泽泻的干燥根茎（日文为 Sentaku））的极性较低的部分中，分离出了三种新的原烷型三萜类化合物，分别命名为泽泻醇 E 23-乙酸酯、F 和 G，以及四种愈创木型倍半萜类化合物和几种已知的三萜类化合物，包括 13，17-表紫苏醇 A。根据化学和物理化学证据，包括 E 23-乙酸烯醇、F 和 G 与已知三萜类烯醇 A 和 A 24-乙酸酯的化学相关性，以及应用改进的莫舍尔法，确定了 E 23-乙酸烯醇、F 和 G 的绝对立体结构。
• 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.
• Murata,T.; Miyamoto,M., Chemical and pharmaceutical bulletin, 1970, vol. 18, p. 1354 - 1361
  作者：Murata,T.、Miyamoto,M.

  DOI：——

  日期：——
• Murata,T. et al., Chemical and pharmaceutical bulletin, 1970, vol. 18, # 7, p. 1369 - 1384
  作者：Murata,T. et al.

  DOI：——

  日期：——