(1R,2S,5S,10S,14R,15R,23R)-18-ethoxycarbonyl-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 | 1391817-27-8

• 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)-18-ethoxycarbonyl-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: 1391817-27-8
• 化学式: C₃₄H₅₀N₂O₄
• 分子量: 550.782
• InChiKey: MZXJBSKVALSZAQ-ZKAMSSCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  92.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S,5S,10S,14R,15R,23R)-18-ethoxycarbonyl-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 在 甲醇 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以53%的产率得到(1R,2S,5S,10S,14R,15R,23R)-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-5,18-dicarboxylic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Oleanolic Acid Derivatives as Novel Inhibitors of Protein Tyrosine Phosphatase 1B

  摘要：

  A series of oleanolic acid (OA) derivatives have been synthesized and their inhibitory effects on PTP1B, TCPTP and related PTPs are evaluated. Some compounds with five-membered heterocyclic ring-fused at C-2, C-3 positions showed a dramatic increase in inhibition, the two most potent PTP1B inhibitors 19 (IC50 = 0.91 mu M) and 21 (IC50 = 0.98 mu M) showed about 3-fold more potent than lead compound OA. Some C-ring modified OA analogs showed high selectivity for PTP1B over TCPTP, among them, 50 possessed the best selectivity of 6.6-fold.

  DOI：

  10.3987/com-12-12445
• 作为产物：
  描述：

  (4aS,6aS,6bR,8aR,12aR,12bR,14bS)-11-(2-ethoxy-2-oxoacetyl)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid 在 一水合肼 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 12.0h， 以78%的产率得到(1R,2S,5S,10S,14R,15R,23R)-18-ethoxycarbonyl-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 Oleanolic Acid Derivatives as Novel Inhibitors of Protein Tyrosine Phosphatase 1B

  摘要：

  A series of oleanolic acid (OA) derivatives have been synthesized and their inhibitory effects on PTP1B, TCPTP and related PTPs are evaluated. Some compounds with five-membered heterocyclic ring-fused at C-2, C-3 positions showed a dramatic increase in inhibition, the two most potent PTP1B inhibitors 19 (IC50 = 0.91 mu M) and 21 (IC50 = 0.98 mu M) showed about 3-fold more potent than lead compound OA. Some C-ring modified OA analogs showed high selectivity for PTP1B over TCPTP, among them, 50 possessed the best selectivity of 6.6-fold.

  DOI：

  10.3987/com-12-12445