3-beta-羟基齐墩果酸苯甲酸酯 | 6153-31-7

• 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: 3-beta-羟基齐墩果酸苯甲酸酯
• 英文名称: (3β)-3-(benzoyloxy)olean-12-en-28-oic acid
• 英文别名: benzoate of oleanolic acid；3β-benzoyloxy-oleanen-(12)-oic acid-(28)；3β-Benzoyloxy-oleanen-(12)-saeure-(28)；Oleanolic acid benzoate；(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-benzoyloxy-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: 6153-31-7
• 化学式: C₃₇H₅₂O₄
• 分子量: 560.817
• InChiKey: AFUJWZAKNFIQGK-RRLKWQEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  41
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-beta-羟基齐墩果酸苯甲酸酯 在 吡啶 、 咪唑 、 lead(IV) acetate 、 sodium hydroxide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 重铬酸吡啶 、 copper diacetate 、 四丁基氟化铵 、 氨 、 diethylzinc 、 lithium 、 二异丁基氢化铝 、 copper(I) bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 氯苯 、 甲苯 、 乙腈 为溶剂， 反应 42.33h， 生成 齐墩果酸
  参考文献：
  名称：

  Enantioselective total synthesis of oleanolic acid, erythrodiol, .beta.-amyrin, and other pentacyclic triterpenes from a common intermediate

  摘要：

  DOI：

  10.1021/ja00072a064
• 作为产物：
  描述：

  齐墩果酸 、 苯甲酸酐 在 吡啶 作用下， 反应 24.0h， 以69%的产率得到3-beta-羟基齐墩果酸苯甲酸酯
  参考文献：
  名称：

  Semi-synthesis of acylated triterpenes from olive-oil industry wastes for the development of anticancer and anti-HIV agents

  摘要：

  A broad set of potential bioactive conjugate compounds has been semi-synthesized through solution and solid-phase organic procedures, coupling two natural pentacyclic triterpene acids, oleanolic (OA) and maslinic acids (MA), at the hydroxyl groups of the A-ring of the triterpene skeleton, with 10 different acyl groups. These acyl OA and MA derivatives have been tested for their anti-proliferative (against the bl6f10 murine melanoma cancer cells) and antiviral (as inhibitors of the HIV-1-protease) effects. Several derivatives have shown high levels of early and total apoptosis (up to 90%). Most of the compounds that exhibited anti-proliferative effects also generated ROS, probably involving the activation of an intrinsic apoptotic route. The only four compounds that did not cause the release of ROS could be related to the participation of a probable extrinsic activation of the apoptosis mechanism. A great number of these acyl OA and MA derivatives have proved to be potent inhibitors of the HIV-1-protease, the most active inhibitors having IC50 values between 0.31 and 15.6 mu M, these values being between 4 and 186 times lower than their non-acylated precursors. The potent activities exhibited in the apoptosis-activation processes and in the inhibition of the HIV-1-protease by some OA and MA acylated derivatives imply that these compounds could be used as new, safe, and effective anticancer and/or antiviral drugs. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.049

文献信息

• Synthesis of oleanolic acid derivatives: In vitro, in vivo and in silico studies for PTP-1B inhibition
  作者：Juan José Ramírez-Espinosa、Maria Yolanda Rios、Paolo Paoli、Virginia Flores-Morales、Guido Camici、Vianey de la Rosa-Lugo、Sergio Hidalgo-Figueroa、Gabriel Navarrete-Vázquez、Samuel Estrada-Soto

  DOI：10.1016/j.ejmech.2014.09.036

  日期：2014.11

  Non-insulin dependent diabetes mellitus is a multifactorial disease that links different metabolic routes: a point of convergence is the enzyme PTP-1B which turns off insulin and leptin receptors involved in glucose and lipid metabolism, respectively. Pentacyclic acid triterpenes such as oleanolic acid (OA) have proved to be excellent PTP-1B inhibitors, thus, the purpose of current work was to generate a series of derivatives that improve the pharmacological effect of OA. Our findings suggest that the presence of the carboxylic acid and/or its corresponding reduction product carbinol derivative (H-bond donor) in C-28 is required to maintain the inhibitory activity: moreover, this is further enhanced by ester or ether formation on C-3. The most active derivatives were cinnamoyl ester (6) and ethyl ether (10). Compound 6 showed potent in vitro inhibitory activity and significantly decrease of blood glucose levels on in vivo experiments. Meanwhile, 10 showed contrasting outcomes, since it was the compound with higher inhibitory activity and selectivity over PTP-1B and has improved interaction with site B, according with docking studies, the in vivo antidiabetic effect was similar to oleanolic acid. In conclusion, oleanolic acid derivatives have revealed an enhanced inhibitory effect over PTP-1B activity by increasing molecular interactions with either catalytic or allosteric sites and producing a hypoglycaemic effect on non insulin dependent diabetes mellitus rat model. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Kuwada; Matsukawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1933, vol. 53, p. 680,685; dtsch. Ref. S. 129
  作者：Kuwada、Matsukawa

  DOI：——

  日期：——