2'-acetyl-triazolo[4',5'-b]-19β,28-epoxy-18αH-oleanane | 1586688-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2'-acetyl-triazolo[4',5'-b]-19β,28-epoxy-18αH-oleanane
• CAS: 1586688-03-0
• 化学式: C₃₂H₄₉N₃O₂
• 分子量: 507.76
• InChiKey: NMFUWMJMJJEOBG-CZZJYRDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 重原子数：
  37.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  57.01
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2'-acetyl-triazolo[4',5'-b]-19β,28-epoxy-18αH-oleanane 在 乙醇 、 potassium hydroxide 作用下， 反应 1.0h， 以79%的产率得到(1R,4aR,6aR,6bR,8aR,13aR,13bR,15aR,15bR)-2,2,6a,6b,9,9,13a-heptamethyl-1,2,3,4,5,6,6a,6b,7,8,8a,9,10,13,13a,13b,14,15,15a,15b-icosahydro-1,4a-(epoxymethano)piceno[2,3-d][1,2,3]triazole
  参考文献：
  名称：

  Synthesis of Triterpene A-Condensed Azoles

  摘要：

  Lupane and 18 alpha H-oleanane alpha-hydroximino ketones were used to synthesize derivatives condensed at ring A with a substituted azole fragment, namely, C(2)-C(3)-fused oxazoles and 1,2,3-triazoles. Triterpene isoxazoles fused at the C(1)-C(2) bond are described for the first time. An optimized method was proposed for the synthesis of unsubstituted 1,2,3-triazoles, displaying cytotoxic activity (IC50 8.4-40.7 mu M) relative to rhabdomyosarcoma, lung carcinoma, and MS melanoma cell lines.

  DOI：

  10.1007/s10593-014-1449-8
• 作为产物：
  描述：

  (1R,4R,5R,8R,11E,13R,14R,17R,18R,19R)-11-hydroxyimino-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[17.3.2.01,18.04,17.05,14.08,13]tetracosan-10-one 、 乙酰肼 在 溶剂黄146 作用下， 反应 4.0h， 以38%的产率得到2'-acetyl-triazolo[4',5'-b]-19β,28-epoxy-18αH-oleanane
  参考文献：
  名称：

  Synthesis of Triterpene A-Condensed Azoles

  摘要：

  Lupane and 18 alpha H-oleanane alpha-hydroximino ketones were used to synthesize derivatives condensed at ring A with a substituted azole fragment, namely, C(2)-C(3)-fused oxazoles and 1,2,3-triazoles. Triterpene isoxazoles fused at the C(1)-C(2) bond are described for the first time. An optimized method was proposed for the synthesis of unsubstituted 1,2,3-triazoles, displaying cytotoxic activity (IC50 8.4-40.7 mu M) relative to rhabdomyosarcoma, lung carcinoma, and MS melanoma cell lines.

  DOI：

  10.1007/s10593-014-1449-8