betulonic acid (6-nitrooxy hexyl) ester | 1187656-28-5

• 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: betulonic acid (6-nitrooxy hexyl) ester
• 英文别名: 6-nitrooxyhexyl betulonate；6-nitrooxyhexyl (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate
• CAS: 1187656-28-5
• 化学式: C₃₆H₅₇NO₆
• 分子量: 599.852
• InChiKey: UXDQYYKRKUMKQG-BYRIPPSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  betulonic acid (6-nitrooxy hexyl) ester 在 吡啶 、 盐酸羟胺 作用下， 反应 24.0h， 以65%的产率得到6-nitrooxyhexyl betulonate-3-oxime
  参考文献：
  名称：

  Novel NO-releasing derivatives of betulinic acid with antitumor activity

  摘要：

  Thirteen novel NO-releasing derivatives of betulinic acid (BA) bearing two types of NO-donors (nitrates and furoxans) were synthesized and evaluated for their antitumor activity. The results showed that furoxan-based derivatives exhibited higher antitumor activity than nitrate-based derivatives, with compounds 11a and 11b displaying promising potency against B16 cell lines and HepG2 cell lines (IC50 < 1 mu mol/L). We supposed that NO-releasing amount of these derivatives which can be detected by Griess method may contribute more to their antitumor activity. As a result, furoxan-based derivatives released larger amount of NO than that of nitrate-based derivatives, which partially explained the higher anti-tumor activity of the former. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.04.002
• 作为产物：
  描述：

  白桦脂酸 在 Jones reagent 、 potassium carbonate 、 silver nitrate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 12.0h， 生成 betulonic acid (6-nitrooxy hexyl) ester
  参考文献：
  名称：

  Novel NO-releasing derivatives of betulinic acid with antitumor activity

  摘要：

  Thirteen novel NO-releasing derivatives of betulinic acid (BA) bearing two types of NO-donors (nitrates and furoxans) were synthesized and evaluated for their antitumor activity. The results showed that furoxan-based derivatives exhibited higher antitumor activity than nitrate-based derivatives, with compounds 11a and 11b displaying promising potency against B16 cell lines and HepG2 cell lines (IC50 < 1 mu mol/L). We supposed that NO-releasing amount of these derivatives which can be detected by Griess method may contribute more to their antitumor activity. As a result, furoxan-based derivatives released larger amount of NO than that of nitrate-based derivatives, which partially explained the higher anti-tumor activity of the former. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.04.002

文献信息

• Design, synthesis, and anti-tumor activity of novel betulinic acid derivatives
  作者：Jin-Hong Liu、Jia Tang、Zi-Fei Zhu、Li Chen

  DOI：10.1080/10286020.2013.870998

  日期：2014.1.2

  Seventeen new derivatives of betulinic acid (BA) with potential anti-tumor activity have been synthesized. In order to improve the bioactivity of BA, we connected BA and nitric oxide donors together via different linkers. The results of the biological activity of these derivatives showed that four compounds exhibited obvious cytotoxicity against human hepatocellular carcinoma cells in vitro.