(2S,4aS,6aS,6bR,8aS,12aS,12bR,14bS)-2,4a,6a,6b,9,9,12a-Heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14b-octadecahydro-picene-2-carboxylic acid methyl ester | 143950-86-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2S,4aS,6aS,6bR,8aS,12aS,12bR,14bS)-2,4a,6a,6b,9,9,12a-Heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14b-octadecahydro-picene-2-carboxylic acid methyl ester
• CAS: 143950-86-1
• 化学式: C₃₁H₄₈O₂
• 分子量: 452.721
• InChiKey: BPGNLUNVEWMMSJ-KMKDQQTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.13
• 重原子数：
  33.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S,4aS,6aS,6bR,8aS,12aS,12bR,14bS)-2,4a,6a,6b,9,9,12a-Heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14b-octadecahydro-picene-2-carboxylic acid methyl ester 在 lithium iodide 作用下， 以 various solvent(s) 为溶剂， 反应 3.0h， 生成 18α-oleana-4,12-dien-30-oic acid
  参考文献：
  名称：

  Glycyrrhetinic acid derivatives as potent inhibitors of Na+, K+-ATPase. Synthesis and structure-activity relationships

  摘要：

  A series of ring A-modified GA derivatives (26 compounds) has been systematically synthesized and the structure-activity relationship investigated for inhibition of canine kidney Na+, K+-ATPase in vitro. The most potent inhibitory activity was found with a group of the 3-deoxygenated derivatives including 5, 6, 9, 10 and 11. The high inhibition may be closely related to the hydrophobic character of the A-ring of these compounds. This finding suggests that the ATP-binding site at the active center of the enzyme is located in a hydrophobic environment.

  DOI：

  10.1016/0223-5234(92)90147-s
• 作为产物：
  描述：

  3β-Hydroxy-18α-Δ¹²-oleanen-30-saeuremethylester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2S,4aS,6aS,6bR,8aS,12aS,12bR,14bS)-2,4a,6a,6b,9,9,12a-Heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14b-octadecahydro-picene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Glycyrrhetinic acid derivatives as potent inhibitors of Na+, K+-ATPase. Synthesis and structure-activity relationships

  摘要：

  A series of ring A-modified GA derivatives (26 compounds) has been systematically synthesized and the structure-activity relationship investigated for inhibition of canine kidney Na+, K+-ATPase in vitro. The most potent inhibitory activity was found with a group of the 3-deoxygenated derivatives including 5, 6, 9, 10 and 11. The high inhibition may be closely related to the hydrophobic character of the A-ring of these compounds. This finding suggests that the ATP-binding site at the active center of the enzyme is located in a hydrophobic environment.

  DOI：

  10.1016/0223-5234(92)90147-s

文献信息

• Anti-tumor-promoter activity of modified glycyrrhetinic acid derivatives. Synthesis and structure-activity relationships
  作者：T Terasawa、T Okada、H Nishino

  DOI：10.1016/0223-5234(92)90088-i

  日期：1992.10

  A series of modified derivatives of 18alpha- and 18beta-glycyrrhetinic acid was systematically synthesized and their structure-activity relationships investigated for inhibition of the promoter activity of 12-O-tetradecanoylphorbol-13-acetate in vitro. Increased hydrophobicity in the A-ring moiety and the presence of an 11-oxo function were shown to be important for the high inhibition. Replacement of the carboxy to the hydroxymethyl group at the 20-position also enhanced the inhibitory activity.