(5aS,6R,9S,9aS)-9-hydroxy-9-(hydroxymethyl)-6-isopropyl-1-oxo-1,3,5a,6,7,8,9,9a-octahydrobenzo[c]oxepine-4-carboxylic acid

• 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: (5aS,6R,9S,9aS)-9-hydroxy-9-(hydroxymethyl)-6-isopropyl-1-oxo-1,3,5a,6,7,8,9,9a-octahydrobenzo[c]oxepine-4-carboxylic acid
• 英文别名: (5aS,6R,9S,9aS)-9-hydroxy-9-(hydroxymethyl)-1-oxo-6-propan-2-yl-3,5a,6,7,8,9a-hexahydro-2-benzoxepine-4-carboxylic acid
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: AKATZNBLBACMHZ-RTWAVKEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (+)-萜烯七脂酸 在 硫酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以68%的产率得到(5aS,6R,9S,9aS)-9-hydroxy-9-(hydroxymethyl)-6-isopropyl-1-oxo-1,3,5a,6,7,8,9,9a-octahydrobenzo[c]oxepine-4-carboxylic acid
  参考文献：
  名称：

  Anticancer activity of koningic acid and semisynthetic derivatives

  摘要：

  A screening program aimed at discovering novel anticancer agents based on natural products led to the selection of koningic acid (KA), known as a potent inhibitor of glycolysis. A method was set up to produce this fungal sesquiterpene lactone in large quantities by fermentation, thus allowing (i) an extensive analysis of its anticancer potential in vitro and in vivo and (ii) the semi-synthesis of analogues to delineate structure-activity relationships. KA was characterized as a potent, but non-selective cytotoxic agent, active under both normoxic and hypoxic conditions and inactive in the A549 lung cancer xenograft model. According to our SAR, the acidic group could be replaced to keep bioactivity but an intact epoxide is essential. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.004

文献信息

• Anticancer activity of koningic acid and semisynthetic derivatives
  作者：Nicolas J. Rahier、Nicolas Molinier、Christophe Long、Sunil Kumar Deshmukh、Abhijeet S. Kate、Prafull Ranadive、Shilpa Amit Verekar、Mangesh Jiotode、Rahul R. Lavhale、Pradipta Tokdar、Arun Balakrishnan、Samuel Meignan、Céline Robichon、Bruno Gomes、Yannick Aussagues、Arnaud Samson、François Sautel、Christian Bailly

  DOI：10.1016/j.bmc.2015.04.004

  日期：2015.7

  A screening program aimed at discovering novel anticancer agents based on natural products led to the selection of koningic acid (KA), known as a potent inhibitor of glycolysis. A method was set up to produce this fungal sesquiterpene lactone in large quantities by fermentation, thus allowing (i) an extensive analysis of its anticancer potential in vitro and in vivo and (ii) the semi-synthesis of analogues to delineate structure-activity relationships. KA was characterized as a potent, but non-selective cytotoxic agent, active under both normoxic and hypoxic conditions and inactive in the A549 lung cancer xenograft model. According to our SAR, the acidic group could be replaced to keep bioactivity but an intact epoxide is essential. (C) 2015 Elsevier Ltd. All rights reserved.