dimethyl ((1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-acetoxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carbonyl)-L-glutamate | 1260709-36-1

• 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: dimethyl ((1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-acetoxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carbonyl)-L-glutamate
• CAS: 1260709-36-1
• 化学式: C₃₉H₆₁NO₇
• 分子量: 655.916
• InChiKey: IGJBOZYIJBCVKT-XFMMSLOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  47.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  108.0
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  dimethyl ((1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-acetoxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carbonyl)-L-glutamate 在 甲醇 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以93.6%的产率得到N-[3β-hydroxy-urs-12-en-28-oyl]-2-amino-1,5-pentanedioic acid
  参考文献：
  名称：

  Synthesis and evaluation of ursolic acid derivatives as potent cytotoxic agents

  摘要：

  Structural modification was performed at the C-3 and C-28 positions of ursolic acid (UA). Ten UA derivatives with distinct electrical property were synthesized. They could be divided into two groups according to their charge under physiological conditions: (1) Group I negatively charged and (2) Group II positively charged. The anti-proliferative capability of the derivatives was evaluated against HepG2, AGS, HT-29 and PC-3 cells by the MTT assay. Flow cytometry and Annexin V/PI dual staining assay were carried out to explore the antitumor mechanism. The results showed the cytotoxic capacity of the compounds was: Group I < UA < Group II. The UA derivatives in Group II exhibited potent cytotoxicity and the enhancement of the lipophilicity could further strengthen the cytotoxicity. Triggering apoptosis and causing cell cycle arrest contributed to the anticancer mechanism. The UA derivative UA-7 had the therapeutic potential in the treatment of gastric carcinoma since it showed potent cytotoxicity, reasonable oil/water partition, enhanced water solubility, and the ability to induce the apoptosis of AGS cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.009
• 作为产物：
  描述：

  熊果酸乙酸酯 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 dimethyl ((1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-acetoxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carbonyl)-L-glutamate
  参考文献：
  名称：

  Synthesis and evaluation of ursolic acid derivatives as potent cytotoxic agents

  摘要：

  Structural modification was performed at the C-3 and C-28 positions of ursolic acid (UA). Ten UA derivatives with distinct electrical property were synthesized. They could be divided into two groups according to their charge under physiological conditions: (1) Group I negatively charged and (2) Group II positively charged. The anti-proliferative capability of the derivatives was evaluated against HepG2, AGS, HT-29 and PC-3 cells by the MTT assay. Flow cytometry and Annexin V/PI dual staining assay were carried out to explore the antitumor mechanism. The results showed the cytotoxic capacity of the compounds was: Group I < UA < Group II. The UA derivatives in Group II exhibited potent cytotoxicity and the enhancement of the lipophilicity could further strengthen the cytotoxicity. Triggering apoptosis and causing cell cycle arrest contributed to the anticancer mechanism. The UA derivative UA-7 had the therapeutic potential in the treatment of gastric carcinoma since it showed potent cytotoxicity, reasonable oil/water partition, enhanced water solubility, and the ability to induce the apoptosis of AGS cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.009