2-carbamoyl-3-hydroxyurs-12-en-24-oic acid | 1285527-55-0

• 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: 2-carbamoyl-3-hydroxyurs-12-en-24-oic acid
• 英文别名: (3S,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-2-carbamoyl-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picene-4-carboxylic acid
• CAS: 1285527-55-0
• 化学式: C₃₁H₄₉NO₄
• 分子量: 499.734
• InChiKey: RRMLYDCBIGXBMD-OIZWTYQOSA-N

物化性质

• 熔点：
  174-176 °C
• 沸点：
  646.3±55.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-carbamoyl-3-hydroxyurs-12-en-24-oic acid 在 氯化亚砜 、 sodium azide 、 三氟乙酸 作用下， 以 水 、 丙酮 、 苯 为溶剂， 反应 6.0h， 生成 (3S,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-4-amino-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picene-2-carboxamide
  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
• 作为产物：
  描述：

  butyl 3-α-acetoxyurs-12-en-24-oate 在 sodium tetrahydroborate 、 盐酸羟胺 、 sodium methylate 、 sodium hydride 、 potassium carbonate 、 pyridinium chlorochromate 、 potassium hydroxide 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 生成 2-carbamoyl-3-hydroxyurs-12-en-24-oic acid
  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.