methyl N-[23-acetoxylup[3,2-c]pyrazole-20(29)-en-28-oyl]glycinate

• 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 N-[23-acetoxylup[3,2-c]pyrazole-20(29)-en-28-oyl]glycinate
• 英文别名: methyl 2-[[(1R,2R,9S,10R,13R,14R,17S,20R,21R,22R)-9-(acetyloxymethyl)-2,9,13,14-tetramethyl-20-prop-1-en-2-yl-6,7-diazahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-4(8),5-diene-17-carbonyl]amino]acetate
• 化学式: C₃₆H₅₃N₃O₅
• 分子量: 607.834
• InChiKey: VBSHRFRWWVIJTQ-VTVFBSSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl N-[23-acetoxylup[3,2-c]pyrazole-20(29)-en-28-oyl]glycinate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 以37.3%的产率得到N-[23-hydroxylup[3,2-b]pyrazine-20(29)-en-28-oyl]glycine
  参考文献：
  名称：

  Synthesis, in vitro and in vivo antitumor activity of pyrazole-fused 23-hydroxybetulinic acid derivatives

  摘要：

  A collection of pyrazole-fused 23-hydroxybetulinic acid derivatives were designed, synthesized and evaluated for their antitumor activity. Most of the newly synthesized compounds exhibited significant antiproliferative activity. Especially compound 15e displayed the most potent activity with the IC50 values of 5.58 and 6.13 mu M against B16 and SF763 cancer cell lines, respectively. Furthermore, the significant in vivo antitumor activity of 15e was validated in H22 liver cancer and B16 melanoma xenograft mouse models. The structure-activity relationships of these 23-hydroxybetulinic acid derivatives were also discussed based on the present investigation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.058
• 作为产物：
  描述：

  23-hydroxybetulinic acid 在 盐酸 、 4-二甲氨基吡啶 、 草酰氯 、 palladium 10% on activated carbon 、 氢气 、 sodium methylate 、 potassium carbonate 、 一水合肼 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 生成 methyl N-[23-acetoxylup[3,2-c]pyrazole-20(29)-en-28-oyl]glycinate
  参考文献：
  名称：

  Synthesis, in vitro and in vivo antitumor activity of pyrazole-fused 23-hydroxybetulinic acid derivatives

  摘要：

  A collection of pyrazole-fused 23-hydroxybetulinic acid derivatives were designed, synthesized and evaluated for their antitumor activity. Most of the newly synthesized compounds exhibited significant antiproliferative activity. Especially compound 15e displayed the most potent activity with the IC50 values of 5.58 and 6.13 mu M against B16 and SF763 cancer cell lines, respectively. Furthermore, the significant in vivo antitumor activity of 15e was validated in H22 liver cancer and B16 melanoma xenograft mouse models. The structure-activity relationships of these 23-hydroxybetulinic acid derivatives were also discussed based on the present investigation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.058