potassium (E)-5-hydroxypent-2-enoate | 1355995-10-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: potassium (E)-5-hydroxypent-2-enoate
• 英文别名: potassium;(E)-5-hydroxypent-2-enoate
• CAS: 1355995-10-6
• 化学式: C₅H₇O₃*K
• 分子量: 154.207
• InChiKey: TYRNZQQYMSSLAK-KSMVGCCESA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -4.32
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,6-dihydro-pyran-2-one 在 potassium hydroxide 作用下， 以 水 为溶剂， 以80%的产率得到potassium (E)-5-hydroxypent-2-enoate
  参考文献：
  名称：

  5- and 6-Membered (thio)lactones are prodrug type carbonic anhydrase inhibitors

  摘要：

  The inhibition of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1) with (thio) coumarins has been recently reported (Maresca et al., J. Am. Chem. Soc. 2009, 131, 3057). Here we demonstrate that a series of gamma- and delta-(thio) lactones also act as mechanism based, prodrug type CA inhibitors, similar to the (thio) coumarins. Through the esterase activity of CA, these compounds are hydrolyzed in situ to the corresponding hydroxy/keto/mercapto acids which thereafter act as inhibitors. CA isoforms I and IX were efficiently inhibited by simple such compounds, with KIs in the range of 0.92-19.1 mu M, whereas CA II was not inhibited at all. Isoform-selective CA inhibitors which spare the ubiquitous off-target CA II may have interesting applications for example for selectively inhibiting the tumor-associated CA IX, a validated anticancer target. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.018