ent-16β-epoxy-kauran-19-oic acid | 1430212-95-5

• 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: ent-16β-epoxy-kauran-19-oic acid
• 英文别名: (1'S,2R,4'S,5'R,9'R,13'R)-5',9'-dimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.01,10.04,9]hexadec-10-ene]-5'-carboxylic acid
• CAS: 1430212-95-5
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: NWNAERNROROJFJ-RCUJSYDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  grandiflorenic acid 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以4%的产率得到ent-16α-epoxy-kauran-19-oic acid
  参考文献：
  名称：

  Synthesis, cytotoxicity and antiplasmodial activity of novel ent -kaurane derivatives

  摘要：

  This paper reports on the syntheses and spectrometric characterisation of eleven novel ent-kaurane diterpenoids, including a complete set of H-1, C-13 NMR and crystallographic data for two novel ent-kaurane diepoxides. Moreover, the antineoplastic cytotoxicity for kaurenoic acid and the majority of ent-kaurane derivatives were assessed in vitro against a panel of fourteen cancer cell lines, of which allylic alcohols were shown to be the most active compounds. The good in vitro antimalarial activity and the higher selectivity index values observed for some ent-kaurane epoxides against the chloroquine-resistant W2 clone of Plasmodium falciparum indicate that this class of natural products may provide new hits for the development of antimalarial drugs. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.010

文献信息

• Synthesis, cytotoxicity and antiplasmodial activity of novel ent -kaurane derivatives
  作者：Ronan Batista、Pablo A. García、María Angeles Castro、José M. Miguel del Corral、Nivaldo L. Speziali、Fernando de P. Varotti、Renata C. de Paula、Luis F. García-Fernández、Andrés Francesch、Arturo San Feliciano、Alaíde B. de Oliveira

  DOI：10.1016/j.ejmech.2012.12.010

  日期：2013.4

  This paper reports on the syntheses and spectrometric characterisation of eleven novel ent-kaurane diterpenoids, including a complete set of H-1, C-13 NMR and crystallographic data for two novel ent-kaurane diepoxides. Moreover, the antineoplastic cytotoxicity for kaurenoic acid and the majority of ent-kaurane derivatives were assessed in vitro against a panel of fourteen cancer cell lines, of which allylic alcohols were shown to be the most active compounds. The good in vitro antimalarial activity and the higher selectivity index values observed for some ent-kaurane epoxides against the chloroquine-resistant W2 clone of Plasmodium falciparum indicate that this class of natural products may provide new hits for the development of antimalarial drugs. (C) 2013 Elsevier Masson SAS. All rights reserved.