(1R,2S,5S,10S,14R,15R,23R)-20-hexanoyl-1,2,8,8,15,22,22-heptamethyl-19,20-diazahexacyclo[12.11.0.02,11.05,10.015,23.017,21]pentacosa-11,17(21),18-triene-5-carboxylic acid | 1202006-30-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1R,2S,5S,10S,14R,15R,23R)-20-hexanoyl-1,2,8,8,15,22,22-heptamethyl-19,20-diazahexacyclo[12.11.0.02,11.05,10.015,23.017,21]pentacosa-11,17(21),18-triene-5-carboxylic acid
• CAS: 1202006-30-1
• 化学式: C₃₇H₅₆N₂O₃
• 分子量: 576.863
• InChiKey: PVAPNFADZYNTGF-BXEYLZRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  42
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  己酰氯 、 pyrazolo[3,4-b]olean-12-en-28-oic acid 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以85%的产率得到(1R,2S,5S,10S,14R,15R,23R)-20-hexanoyl-1,2,8,8,15,22,22-heptamethyl-19,20-diazahexacyclo[12.11.0.02,11.05,10.015,23.017,21]pentacosa-11,17(21),18-triene-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B

  摘要：

  A series of maslinic acid derivatives have been synthesized by introducing various fused heterocyclic rings at C-2 and C-3 positions. Their inhibitory effects on PTP1B, TCPTP and related PTPs are evaluated. Most of the compounds exhibited a dramatic increase in inhibitory potency and selectivity, the two most potent PTP1B inhibitors 20 (IC50 = 0.61 mu M) and 29 (IC50 = 0.64 mu M) showed about 10-fold more potent than lead compound maslinic acid. More importantly, 29 possesses the best selectivity of 6.9-fold for PTP1B over TCPTP. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.017

文献信息

• Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B
  作者：Wen-Wei Qiu、Qiang Shen、Fan Yang、Bo Wang、Hui Zou、Jing-Ya Li、Jia Li、Jie Tang

  DOI：10.1016/j.bmcl.2009.10.017

  日期：2009.12

  A series of maslinic acid derivatives have been synthesized by introducing various fused heterocyclic rings at C-2 and C-3 positions. Their inhibitory effects on PTP1B, TCPTP and related PTPs are evaluated. Most of the compounds exhibited a dramatic increase in inhibitory potency and selectivity, the two most potent PTP1B inhibitors 20 (IC50 = 0.61 mu M) and 29 (IC50 = 0.64 mu M) showed about 10-fold more potent than lead compound maslinic acid. More importantly, 29 possesses the best selectivity of 6.9-fold for PTP1B over TCPTP. (C) 2009 Elsevier Ltd. All rights reserved.