(ethoxycarbonyl)methyl 2α,3β,23-trihydroxyurs-12-en-28-oate | 1195758-14-5

• 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: (ethoxycarbonyl)methyl 2α,3β,23-trihydroxyurs-12-en-28-oate
• CAS: 1195758-14-5
• 化学式: C₃₄H₅₄O₇
• 分子量: 574.799
• InChiKey: CKVFXLNTAXUGNI-ADOMMCJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  41.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  113.29
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (ethoxycarbonyl)methyl 2α,3β,23-trihydroxyurs-12-en-28-oate 在 氨 、 肼 作用下， 以 乙醇 为溶剂， 生成 (1S,2R,4aS,6aS,6bR,9R,10R,11R,12aR,14bS) (2-hydrazinyl(2-oxoethyl))-10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of asiatic acid derivatives as anti-fibrotic agents: Structure/activity studies

  摘要：

  Fibrotic diseases are characterized by the over-accumulation of fibrous components in the extracellular matrix and the liver, which can lead to liver cirrhosis. Current treatment options cannot reverse or halt liver fibrosis, motivating a search for newer treatment options. Previously, we showed that asiaticoside, a bioactive triterpene glycoside from Centella asiatica, has anti-fibrotic properties. Here, the aglycone asiatic acid was chemically modified, and these derivatives were evaluated for their potential as anti-fibrotic agents. The data obtained from in vivo testing of these compounds in a rodent CCl4-induced liver injury model are discussed. The information obtained from these studies may be useful in the design of novel anti-fibrotic agents. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.11.001
• 作为产物：
  描述：

  积雪草苷 在 盐酸 、 potassium carbonate 、 三乙胺 、 potassium iodide 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 (ethoxycarbonyl)methyl 2α,3β,23-trihydroxyurs-12-en-28-oate
  参考文献：
  名称：

  Synthesis and evaluation of asiatic acid derivatives as anti-fibrotic agents: Structure/activity studies

  摘要：

  Fibrotic diseases are characterized by the over-accumulation of fibrous components in the extracellular matrix and the liver, which can lead to liver cirrhosis. Current treatment options cannot reverse or halt liver fibrosis, motivating a search for newer treatment options. Previously, we showed that asiaticoside, a bioactive triterpene glycoside from Centella asiatica, has anti-fibrotic properties. Here, the aglycone asiatic acid was chemically modified, and these derivatives were evaluated for their potential as anti-fibrotic agents. The data obtained from in vivo testing of these compounds in a rodent CCl4-induced liver injury model are discussed. The information obtained from these studies may be useful in the design of novel anti-fibrotic agents. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.11.001

文献信息

• Synthesis and Biological Evaluation of Asiatic Acid Derivatives as Inhibitors of Glycogen Phosphorylases
  作者：Liying Zhang、Jun Chen、Yanchun Gong、Jun Liu、Luyong Zhang、Weiyi Hua、Hongbin Sun

  DOI：10.1002/cbdv.200800092

  日期：2009.6

  Twenty-four asiatic acid derivatives have been synthesized and biologically evaluated as inhibitors of glycogen phosphorylase (GP). Within this series of compounds, asiatic acid benzyl ester (23; IC(50)=3.8 microM) exhibited more potent activity than its parent compound 1 (IC(50)=17 microM). SAR Analysis showed that asiatic acid (1) possessing a 2alpha-OH function exhibited more potent GP inhibitory

  已经合成了 24 种积雪草酸衍生物并在生物学上评估了它们作为糖原磷酸化酶 (GP) 的抑制剂。在这一系列的化合物中，积雪草酸苄酯 (23; IC(50)=3.8 microM) 表现出比其母体化合物 1 (IC(50)=17 microM) 更有效的活性。SAR 分析表明，具有 2alpha-OH 功能的积雪草酸 (1) 比具有 2beta-OH 功能的 eriantic acid B (27) 表现出更有效的 GP 抑制活性。需要基于 1 进行进一步的先导优化，以找到更有效的积雪草酸衍生物作为对缺血性糖尿病并发症具有保护作用的抗糖尿病药物。
• 一种积雪草酸衍生物
  申请人：四川大学

  公开号：CN104341480B

  公开（公告）日：2016-05-04

  本发明提供了一种基于积雪草酸结构进行修饰的衍生物。本发明药理活性实验表明，本发明化合物(特别是5a、5b、5d、5f)有较好的抗纤维化活性，且化合物的脂溶性较积雪草酸有所提高，为临床用药提供了新的选择。