benzyl 23-hydroxy-lup[3,2-b]pyrazine-20(29)-en-28-oate

• 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: benzyl 23-hydroxy-lup[3,2-b]pyrazine-20(29)-en-28-oate
• 英文别名: benzyl (1R,2R,10S,11R,14R,15R,18S,21R,22R,23R)-10-(hydroxymethyl)-2,10,14,15-tetramethyl-21-prop-1-en-2-yl-5,8-diazahexacyclo[12.11.0.02,11.04,9.015,23.018,22]pentacosa-4,6,8-triene-18-carboxylate
• 化学式: C₃₉H₅₂N₂O₃
• 分子量: 596.853
• InChiKey: SOEPGPDCFPVGEE-OUGOKLMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  44
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 23-hydroxy-lup[3,2-b]pyrazine-20(29)-en-28-oate 、 乙酸酐 在 吡啶 作用下， 以86%的产率得到benzyl 23-acetoxy-lup[3,2-b]pyrazine-20(29)-en-28-oate
  参考文献：
  名称：

  Design, synthesis and antitumor activity of triterpenoid pyrazine derivatives from 23-hydroxybetulinic acid

  摘要：

  Pyrazine-fused 23-hydroxybetulinic acid was synthesized by introducing a pyrazine ring between C-2 and C-3 position and further modifications were carried out by substitution of C-28 carboxyl group by ester and amide linkage to enhance the antitumor activity. The biological screening results showed that all of the derivatives exhibited more significant antiproliferative activity than the parent compound. In particular compound 12a exhibited the most potent activity with IC50 values of 3.53 mu M, 4.42 mu M and 5.13 mu M against cell lines SF-763, B16 and Hela, respectively. In the preliminary mechanism study, 12a caused cell arrest in G1 phase and significantly induced apoptosis of B16 cells in a dose-dependent manner. Furthermore, the in vivo antitumor activity of 12a was validated (tumor inhibitory ratio of 55.6% and 62.7%, respectively) in mice with H22 liver cancer and B16 melanoma (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.057
• 作为产物：
  描述：

  23-hydroxybetulinic acid 在 吗啉 、 盐酸 、 4-二甲氨基吡啶 、 potassium carbonate 、 sulfur 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 benzyl 23-hydroxy-lup[3,2-b]pyrazine-20(29)-en-28-oate
  参考文献：
  名称：

  Design, synthesis and antitumor activity of triterpenoid pyrazine derivatives from 23-hydroxybetulinic acid

  摘要：

  Pyrazine-fused 23-hydroxybetulinic acid was synthesized by introducing a pyrazine ring between C-2 and C-3 position and further modifications were carried out by substitution of C-28 carboxyl group by ester and amide linkage to enhance the antitumor activity. The biological screening results showed that all of the derivatives exhibited more significant antiproliferative activity than the parent compound. In particular compound 12a exhibited the most potent activity with IC50 values of 3.53 mu M, 4.42 mu M and 5.13 mu M against cell lines SF-763, B16 and Hela, respectively. In the preliminary mechanism study, 12a caused cell arrest in G1 phase and significantly induced apoptosis of B16 cells in a dose-dependent manner. Furthermore, the in vivo antitumor activity of 12a was validated (tumor inhibitory ratio of 55.6% and 62.7%, respectively) in mice with H22 liver cancer and B16 melanoma (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.057