(2β,3α)-2,3-二羟基齐墩果-12-烯-28-酸 | 5957-40-4

• 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
• 中文名称: (2β,3α)-2,3-二羟基齐墩果-12-烯-28-酸
• 中文别名: 1-甲基-1H-吡唑-4-甲酸；(2betaalpha,3alpha)-2,3-二羟基齐墩果-12-烯-28-酸；1-甲基吡唑-4-甲酸
• 英文名称: (2β,3α)-dihydroxyolean-12-en-28-oic acid
• 英文别名: bredemolic acid；Bredemolsaeure；(4aS,6aR,6aS,6bR,8aR,10S,11S,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 5957-40-4
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: MDZKJHQSJHYOHJ-SXISEVPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2β,3α)-2,3-二羟基齐墩果-12-烯-28-酸 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.08h， 生成 2β,3α-diacetyloxyolean-12-en-28-oic acid benzylamide
  参考文献：
  名称：

  Urea derivates of ursolic, oleanolic and maslinic acid induce apoptosis and are selective cytotoxic for several human tumor cell lines

  摘要：

  2,3-Di-O-acetyl-maslinic acid benzylamide (5) has previously been shown to possess high cytotoxicity for a variety of human tumor cell lines while being of low cytotoxicity to non-malignant cells. Structural modifications performed on 5 revealed that the presence of these acetyl groups in 5 and the presence of (2 beta,3 beta)-configurated centers seems necessary for obtaining high cytotoxicity combined with best selectivity between malignant cells and non-malignant mouse fibroblasts. Compounds carrying an ursane skeleton showed weaker cytotoxicity than their oleanane derived analogs. In addition, the benzylamide function in compound 5 should be replaced by a phenylurea moiety to gain better cytotoxicity while retaining and improving the selectivity. Thus, maslinic acid derived N-[2 beta,3 beta-di-O-acetyl-17 beta-amino-28-norolean-12-en-17-yliphenylurea (45) gave best results showing EC50 = 0.9 mu M (for A2780 ovarian cancer cells) with EC50 > 120 mu M for fibroblasts (NIH 3T3) and triggered apoptosis while caspase-3 was not activated by this compound. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.051
• 作为产物：
  描述：

  benzyl 2β,3α-dihydroxyolean-12-en-28-oate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以86%的产率得到(2β,3α)-2,3-二羟基齐墩果-12-烯-28-酸
  参考文献：
  名称：

  实用的溴乙酸的合成，它是糖原磷酸化酶的天然抑制剂。

  摘要：

  布雷地摩尔酸（3）是山梨酸（1）的天然2beta，3alpha异构体，是糖原磷酸化酶（GP）的变构位点抑制剂。从容易获得的2beta，3beta-二醇6a开始，分5个步骤完成了3的实际合成（产率为18％）。以类似的方式，合成了2β，3α-二羟基urs-12-en-28-oic酸（4），作为天然的β2，3α-椰油酸（2）。化合物3和4对兔肌肉GPa表现出显着的抑制活性，IC（50）值分别为6.25和1.1μM。

  DOI：

  10.1021/np8003886

文献信息

• Straightforward partial synthesis of four diastereomeric 2,3-dihydroxy-olean-12-en-28-oic acids from oleanolic acid
  作者：Sven Sommerwerk、Lucie Heller、Immo Serbian、René Csuk

  DOI：10.1016/j.tet.2015.09.037

  日期：2015.11

  The four diastereomeric 2,3-dihydroxy-olean-12-en-28-oic acids (maslinic, augustic, bredemolic and 3-epi-maslinic acid) were easily accessed from one single starting material, oleanolic acid. The procedures allow the medium-to-large scale preparation of these valuable starting materials. Except for maslinic acid, the triterpenoic acids showed only a low cytotoxicity towards several human tumor cell lines. (C) 2015 Elsevier Ltd. All rights reserved.
• Urea derivates of ursolic, oleanolic and maslinic acid induce apoptosis and are selective cytotoxic for several human tumor cell lines
  作者：Sven Sommerwerk、Lucie Heller、Julia Kuhfs、René Csuk

  DOI：10.1016/j.ejmech.2016.04.051

  日期：2016.8

  2,3-Di-O-acetyl-maslinic acid benzylamide (5) has previously been shown to possess high cytotoxicity for a variety of human tumor cell lines while being of low cytotoxicity to non-malignant cells. Structural modifications performed on 5 revealed that the presence of these acetyl groups in 5 and the presence of (2 beta,3 beta)-configurated centers seems necessary for obtaining high cytotoxicity combined with best selectivity between malignant cells and non-malignant mouse fibroblasts. Compounds carrying an ursane skeleton showed weaker cytotoxicity than their oleanane derived analogs. In addition, the benzylamide function in compound 5 should be replaced by a phenylurea moiety to gain better cytotoxicity while retaining and improving the selectivity. Thus, maslinic acid derived N-[2 beta,3 beta-di-O-acetyl-17 beta-amino-28-norolean-12-en-17-yliphenylurea (45) gave best results showing EC50 = 0.9 mu M (for A2780 ovarian cancer cells) with EC50 > 120 mu M for fibroblasts (NIH 3T3) and triggered apoptosis while caspase-3 was not activated by this compound. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Practical Synthesis of Bredemolic Acid, a Natural Inhibitor of Glycogen Phosphorylase
  作者：Keguang Cheng、Pu Zhang、Jun Liu、Juan Xie、Hongbin Sun

  DOI：10.1021/np8003886

  日期：2008.12.1

  Bredemolic acid (3) is a naturally occurring 2beta,3alpha-isomer of maslinic acid (1) that is an allosteric site inhibitor of glycogen phosphorylase (GP). A practical synthesis of 3 was accomplished (18% yield) in five steps starting from the readily available 2beta,3beta-diol 6a. In a similar fashion, 2beta,3alpha-dihydroxyurs-12-en-28-oic acid (4) was synthesized as a natural 2beta,3alpha-isomer

  布雷地摩尔酸（3）是山梨酸（1）的天然2beta，3alpha异构体，是糖原磷酸化酶（GP）的变构位点抑制剂。从容易获得的2beta，3beta-二醇6a开始，分5个步骤完成了3的实际合成（产率为18％）。以类似的方式，合成了2β，3α-二羟基urs-12-en-28-oic酸（4），作为天然的β2，3α-椰油酸（2）。化合物3和4对兔肌肉GPa表现出显着的抑制活性，IC（50）值分别为6.25和1.1μM。