benzyl (4aS,6aS,6bR,8aR,13aR,13bR,15bS)-2,2,6a,6b,9,9,11,13a-octamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,13,13a,13b,14,15b-hexadecahydropiceno[2,3-d]oxazole-4a(2H)-carboxylate | 1391817-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (4aS,6aS,6bR,8aR,13aR,13bR,15bS)-2,2,6a,6b,9,9,11,13a-octamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,13,13a,13b,14,15b-hexadecahydropiceno[2,3-d]oxazole-4a(2H)-carboxylate
• CAS: 1391817-18-7
• 化学式: C₃₉H₅₃NO₃
• 分子量: 583.855
• InChiKey: XHDNYWRFRQZHJE-BCSPCWQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.54
• 重原子数：
  43.0
• 可旋转键数：
  3.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  52.33
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  benzyl (4aS,6aS,6bR,8aR,13aR,13bR,15bS)-2,2,6a,6b,9,9,11,13a-octamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,13,13a,13b,14,15b-hexadecahydropiceno[2,3-d]oxazole-4a(2H)-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以82%的产率得到(1R,2S,5S,10S,14R,15R,23R)-1,2,8,8,15,19,22,22-octamethyl-20-oxa-18-azahexacyclo[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
• 作为产物：
  描述：

  3-氧代齐墩果烷-12-烯-28-酸苯甲酯 在 potassium tert-butylate 、 锌 、 三氯氧磷 作用下， 以 吡啶 、 溶剂黄146 、 叔丁醇 为溶剂， 反应 30.0h， 生成 benzyl (4aS,6aS,6bR,8aR,13aR,13bR,15bS)-2,2,6a,6b,9,9,11,13a-octamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,13,13a,13b,14,15b-hexadecahydropiceno[2,3-d]oxazole-4a(2H)-carboxylate
  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