butyl 2-cyano-3-oxoursa-1,12-dien-24-oate | 1285527-52-7

• 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: butyl 2-cyano-3-oxoursa-1,12-dien-24-oate
• 英文别名: butyl (4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-2-cyano-4,6a,6b,8a,11,12,14b-heptamethyl-3-oxo-4a,5,6,7,8,9,10,11,12,12a,14,14a-dodecahydropicene-4-carboxylate
• CAS: 1285527-52-7
• 化学式: C₃₅H₅₁NO₃
• 分子量: 533.795
• InChiKey: QMFDTBNRBOOEBO-IJLSBMEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  butyl 3-α-acetoxyurs-12-en-24-oate 在 盐酸羟胺 、 sodium methylate 、 sodium hydride 、 potassium carbonate 、 pyridinium chlorochromate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 1.0h， 生成 butyl 2-cyano-3-oxoursa-1,12-dien-24-oate
  参考文献：
  名称：

  A comparative study of proapoptotic potential of cyano analogues of boswellic acid and 11-keto-boswellic acid

  摘要：

  Semi-synthetic analogues of beta-boswellic acid (BA) and 11-keto-beta-boswellic acid (MBA) were comparatively evaluated for in vitro cytotoxicity against human myeloid leukaemia (HL-60) and human cervical carcinoma (HeLa) cells. 2-Cyano analogues of both the triterpenes were observed to have significant cytotoxicity against both the cells, displaying cytotoxicity in HL-60 cells at low concentrations. Further investigations suggested the proapoptotic potential associated with the two molecules to induce cytotoxicity in HL-60 cells, where one of them showed early proapoptotic effect as evidenced by several biological end-points of the apoptosis such as annexinV binding, DNA fragmentation and increase in sub-G0 DNA fraction and apoptotic bodies formation (Hoechst 33258 staining and SEM studies). (c) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.061

文献信息

• A comparative study of proapoptotic potential of cyano analogues of boswellic acid and 11-keto-boswellic acid
  作者：Rajbir Kaur、Sheema Khan、Renu Chib、Tandeep Kaur、Parduman Raj Sharma、Jaswant Singh、Bhahwal Ali Shah、Subhash Chandra Taneja

  DOI：10.1016/j.ejmech.2011.01.061

  日期：2011.4

  Semi-synthetic analogues of beta-boswellic acid (BA) and 11-keto-beta-boswellic acid (MBA) were comparatively evaluated for in vitro cytotoxicity against human myeloid leukaemia (HL-60) and human cervical carcinoma (HeLa) cells. 2-Cyano analogues of both the triterpenes were observed to have significant cytotoxicity against both the cells, displaying cytotoxicity in HL-60 cells at low concentrations. Further investigations suggested the proapoptotic potential associated with the two molecules to induce cytotoxicity in HL-60 cells, where one of them showed early proapoptotic effect as evidenced by several biological end-points of the apoptosis such as annexinV binding, DNA fragmentation and increase in sub-G0 DNA fraction and apoptotic bodies formation (Hoechst 33258 staining and SEM studies). (c) 2011 Elsevier Masson SAS. All rights reserved.