butyl (1R,2S,5R,8R,9S,10R,14R,15S,22R,23R)-1,2,5,8,9,15,22-heptamethyl-13-oxo-20-oxa-19-azahexacyclo[12.11.0.02,11.05,10.015,23.017,21]pentacosa-11,17(21),18-triene-22-carboxylate | 1285527-48-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: butyl (1R,2S,5R,8R,9S,10R,14R,15S,22R,23R)-1,2,5,8,9,15,22-heptamethyl-13-oxo-20-oxa-19-azahexacyclo[12.11.0.02,11.05,10.015,23.017,21]pentacosa-11,17(21),18-triene-22-carboxylate
• CAS: 1285527-48-1
• 化学式: C₃₅H₅₁NO₄
• 分子量: 549.794
• InChiKey: DIIAOIIALKCMJD-HACYNSBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  butyl (1R,2S,5R,8R,9S,10R,14R,15S,22R,23R)-1,2,5,8,9,15,22-heptamethyl-13-oxo-20-oxa-19-azahexacyclo[12.11.0.02,11.05,10.015,23.017,21]pentacosa-11,17(21),18-triene-22-carboxylate 在 sodium tetrahydroborate 、 氯化亚砜 、 sodium azide 、 sodium methylate 、 三氟乙酸 、 potassium hydroxide 作用下， 以 甲醇 、 乙醚 、 水 、 丙酮 、 苯 为溶剂， 反应 6.0h， 生成 (3S,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-4-amino-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4a,5,6,7,8,9,10,11,12,12a,14a-tetradecahydropicene-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：

  乙酰基-11-酮基-beta-乳香酸 在 氯化亚砜 、 盐酸羟胺 、 sodium hydride 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 、 苯 为溶剂， 反应 3.0h， 生成 butyl (1R,2S,5R,8R,9S,10R,14R,15S,22R,23R)-1,2,5,8,9,15,22-heptamethyl-13-oxo-20-oxa-19-azahexacyclo[12.11.0.02,11.05,10.015,23.017,21]pentacosa-11,17(21),18-triene-22-carboxylate
  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.