3β-Amino-18β-H-urs-12-en-28-oic acid methyl ester | 72808-24-3

• 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: 3β-Amino-18β-H-urs-12-en-28-oic acid methyl ester
• 英文别名: 3β-aminours-12-en-28-oic acid methyl ester；methyl (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-amino-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
• CAS: 72808-24-3
• 化学式: C₃₁H₅₁NO₂
• 分子量: 469.751
• InChiKey: RUPNCBDOIDYUBE-QHQGJMPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-Keto-熊果酸-28-甲酯 在 吡啶 、 titanium(III) chloride 、 盐酸羟胺 、 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 、 水 为溶剂， 反应 14.0h， 生成 3β-Amino-18β-H-urs-12-en-28-oic acid methyl ester
  参考文献：
  名称：

  The cytotoxic activity of ursolic acid derivatives

  摘要：

  Ursolic acid and 2a-hydroxyursolic acid isolated from apple peels were found to show growth inhibitory activity against four tumor cell lines, HL-60, BGC, Bel-7402 and Hela. Structural modifications were performed on the C-3, C-28 and C-11 positions of ursolic acid and the cytotoxicity of the derivatives was evaluated. The SAR revealed that the triterpenes possessing two hydrogen-bond forming groups (an H-donor and a carbonyl group) at positions 3 and 28 exhibit cytotoxic activity. The configuration at C-3 was found to be important for the activity. Introduction of an amino group increased the cytotoxicity greatly. A 3 beta-amino derivative was 20 times more potent than the parent ursolic acid. The 28-aminoalkyl dimer compounds showed selective cytotoxicity. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.01.001

文献信息

• Jain, S. M.; Atal, C. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 427 - 428
  作者：Jain, S. M.、Atal, C. K.

  DOI：——

  日期：——