4-[[(2R,3R,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-benzyloxycarbonyl-3-(4-hydroxy-4-oxo-butanoyl)oxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-2-yl]oxy]-4-oxo-butanoic acid | 1575561-65-7

• 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
• 英文名称: 4-[[(2R,3R,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-benzyloxycarbonyl-3-(4-hydroxy-4-oxo-butanoyl)oxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-2-yl]oxy]-4-oxo-butanoic acid
• 英文别名: 4-[[(2R,3R,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-3-(3-carboxypropanoyloxy)-4,4,6a,6b,11,11,14b-heptamethyl-8a-phenylmethoxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-2-yl]oxy]-4-oxobutanoic acid
• CAS: 1575561-65-7
• 化学式: C₄₅H₆₂O₁₀
• 分子量: 762.981
• InChiKey: KUAJWEOPPJYZHV-YIXMARSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  55
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  丁二酸酐 、 马斯里酸苄酯; (2alpha,3beta)-2,3-二羟基齐墩果-12-烯-28-酸苄酯 在 吡啶 作用下， 反应 24.0h， 以27%的产率得到4-[[(2R,3R,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-benzyloxycarbonyl-3-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-2-yl]oxy]-4-oxo-butanoic acid
  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

• Semi-synthesis of acylated triterpenes from olive-oil industry wastes for the development of anticancer and anti-HIV agents
  作者：Andres Parra、Samuel Martin-Fonseca、Francisco Rivas、Fernando J. Reyes-Zurita、Marta Medina-O'Donnell、Antonio Martinez、Andres Garcia-Granados、Jose A. Lupiañez、Fernando Albericio

  DOI：10.1016/j.ejmech.2013.12.049

  日期：2014.3

  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.