methyl (4aS,6aS,6bR,8aR,14aR,14bR,16bS)-2,2,6a,6b,9,9,14a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,14,14a,14b,15,16b-hexadecahydrochryseno[1,2-g]quinazoline-4a(2H)-carboxylate | 53311-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: methyl (4aS,6aS,6bR,8aR,14aR,14bR,16bS)-2,2,6a,6b,9,9,14a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,14,14a,14b,15,16b-hexadecahydrochryseno[1,2-g]quinazoline-4a(2H)-carboxylate
• CAS: 53311-97-0
• 化学式: C₃₃H₄₈N₂O₂
• 分子量: 504.756
• InChiKey: UUAZDZKHEQSOOC-CEJXBKOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  37.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  52.08
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (4aS,6aS,6bR,8aR,14aR,14bR,16bS)-2,2,6a,6b,9,9,14a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,14,14a,14b,15,16b-hexadecahydrochryseno[1,2-g]quinazoline-4a(2H)-carboxylate 在 lithium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以74%的产率得到(1R,2R,11R,14R,15S,18S,23S)-2,10,10,14,15,21,21-heptamethyl-6,8-diazahexacyclo[12.12.0.02,11.04,9.015,24.018,23]hexacosa-4,6,8,24-tetraene-18-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
• 作为产物：
  描述：

  、 醋酸甲脒 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以78%的产率得到methyl (4aS,6aS,6bR,8aR,14aR,14bR,16bS)-2,2,6a,6b,9,9,14a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,14,14a,14b,15,16b-hexadecahydrochryseno[1,2-g]quinazoline-4a(2H)-carboxylate
  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