methyl (3R,4R,5R,8R,9R,10R,13S,14R,15R)-4-(cyanomethyl)-3-(1-hydroxy-2-methylpropan-2-yl)-4,9,10-trimethyl-15-(prop-1-en-2-yl)hexadecahydro-13H-cyclopenta[a]phenanthrene-13-carboxylate | 1234627-80-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: methyl (3R,4R,5R,8R,9R,10R,13S,14R,15R)-4-(cyanomethyl)-3-(1-hydroxy-2-methylpropan-2-yl)-4,9,10-trimethyl-15-(prop-1-en-2-yl)hexadecahydro-13H-cyclopenta[a]phenanthrene-13-carboxylate
• CAS: 1234627-80-5
• 化学式: C₃₁H₄₉NO₃
• 分子量: 483.735
• InChiKey: SQNFPZHBKYGNED-SRACOBAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.93
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  70.32
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,2-二甲基琥珀酸酐 、 methyl (3R,4R,5R,8R,9R,10R,13S,14R,15R)-4-(cyanomethyl)-3-(1-hydroxy-2-methylpropan-2-yl)-4,9,10-trimethyl-15-(prop-1-en-2-yl)hexadecahydro-13H-cyclopenta[a]phenanthrene-13-carboxylate 在 吡啶 、 4-二甲氨基吡啶 作用下， 以40%的产率得到methyl 3-(3',3'-dimethylsuccinyloxy)-1-cyano-2,3-seco-2-norlup-20(29)-en-28-oate
  参考文献：
  名称：

  Synthesis and antiviral activity of C-3(C-28)-substituted 2,3-seco-triterpenoids

  摘要：

  用四种结构类型的β-氨基醇与2,3-seco-18αH-普罗兰酸和2,3-seco-路烯C-3(C-28)单羧酸及二羧酸合成了酰胺共轭物。通过A-seco-三萜丙醇衍生物与二羧酸酸酐反应制备了酯类化合物。合成化合物的抗病毒活性在对抗一型单纯疱疹病毒时进行了研究。最活跃的酰胺是5a (5.7 μM, MTC/EC50 32.2)。

  DOI：

  10.1007/s10600-014-0821-3
• 作为产物：
  描述：

  2-hydroxyimino-3-oxolup-20(29)-en-28-oic acid methyl ester 在 吡啶 、 sodium tetrahydroborate 、 对甲苯磺酰氯 作用下， 以 甲醇 为溶剂， 反应 0.75h， 生成 methyl (3R,4R,5R,8R,9R,10R,13S,14R,15R)-4-(cyanomethyl)-3-(1-hydroxy-2-methylpropan-2-yl)-4,9,10-trimethyl-15-(prop-1-en-2-yl)hexadecahydro-13H-cyclopenta[a]phenanthrene-13-carboxylate
  参考文献：
  名称：

  The immunotropic activity of lupane and oleanane 2,3-seco-triterpenoids

  摘要：

  The immunotropic effect of the 2,3-seco derivatives of allobetulon, betulonic acid, and the methyl ester of betulonic acid were studied. It was found that the highest activity is shown by compounds with an oleanane fragment. The presence of a free C28-carboxyl group enhances the activity of lupane 2,3-seco derivatives. A significant contribution to the development of the immune response is introduced by a functional group at the C3 atom in the A ring-the C3-carboxy derivatives intensify the processes of antibody production and alter the number and ratio of leukocyte forms. It is shown that 2,3-seco-1-cyano-19 beta,28-epoxy-18 alpha-olean-3-oic acid stimulates humoral immunity with a positive influence on hematopoiesis.

  DOI：

  10.1134/s1068162010020147