methyl 2-[[(1R,2R,14R,17R,18R,21S,24R,25R,26R)-2,13,13,17,18-pentamethyl-24-prop-1-en-2-yl-11-azaheptacyclo[15.11.0.02,14.04,12.05,10.018,26.021,25]octacosa-4(12),5,7,9-tetraene-21-carbonyl]amino]acetate | 905838-13-3

• 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 2-[[(1R,2R,14R,17R,18R,21S,24R,25R,26R)-2,13,13,17,18-pentamethyl-24-prop-1-en-2-yl-11-azaheptacyclo[15.11.0.02,14.04,12.05,10.018,26.021,25]octacosa-4(12),5,7,9-tetraene-21-carbonyl]amino]acetate
• CAS: 905838-13-3
• 化学式: C₃₉H₅₄N₂O₃
• 分子量: 598.869
• InChiKey: JBZHYMNOZSKGBU-FYMBSHNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.13
• 重原子数：
  44.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  71.19
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 2-[[(1R,2R,14R,17R,18R,21S,24R,25R,26R)-2,13,13,17,18-pentamethyl-24-prop-1-en-2-yl-11-azaheptacyclo[15.11.0.02,14.04,12.05,10.018,26.021,25]octacosa-4(12),5,7,9-tetraene-21-carbonyl]amino]acetate 在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N-glycine-[3,2b]indolo-lup-20(29)-en-28-amide
  参考文献：
  名称：

  Synthesis and cytotoxic activity of heterocyclic ring-substituted betulinic acid derivatives

  摘要：

  A new series of betulinic acid derivatives have been synthesized by introducing heterocyclic ring between C-2 and C-3 positions of betulinic acid. Further modi. cations were also carried out by reduction of C-20(29) unsaturated bond and substitution of C-28 carboxyl group by ester and amide linkage to enhance the selectivity. Compound 11 resulted in IC50 of 2.44, 2.5, and 2.7 mu g/ml on MIAPaCa, PA-1, and SW620 cancer cell lines, respectively. Compound 38 resulted in IC50 of 0.67 mu g/ml on MIAPaCa cell line. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.003
• 作为产物：
  描述：

  (1R,3aS,5aR,5bR,7aR,14aR,14bR,16aR,16bR)-5a,5b,8,8,14a-pentamethyl-1-(prop-1-en-2-yl)-2,3,4,5,5a,5b,6,7,7a,8,9,14,14a,14b,15,16,16a,16b-octadecahydrocyclopenta[7,8]phenanthro[2,1-b]carbazole-3a(1H)-carbonyl chloride 、 甘胺酸甲酯 生成 methyl 2-[[(1R,2R,14R,17R,18R,21S,24R,25R,26R)-2,13,13,17,18-pentamethyl-24-prop-1-en-2-yl-11-azaheptacyclo[15.11.0.02,14.04,12.05,10.018,26.021,25]octacosa-4(12),5,7,9-tetraene-21-carbonyl]amino]acetate
  参考文献：
  名称：

  Synthesis and cytotoxic activity of heterocyclic ring-substituted betulinic acid derivatives

  摘要：

  A new series of betulinic acid derivatives have been synthesized by introducing heterocyclic ring between C-2 and C-3 positions of betulinic acid. Further modi. cations were also carried out by reduction of C-20(29) unsaturated bond and substitution of C-28 carboxyl group by ester and amide linkage to enhance the selectivity. Compound 11 resulted in IC50 of 2.44, 2.5, and 2.7 mu g/ml on MIAPaCa, PA-1, and SW620 cancer cell lines, respectively. Compound 38 resulted in IC50 of 0.67 mu g/ml on MIAPaCa cell line. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.003