Z-3-(5-benzylidene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester | 518358-06-0

• 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: Z-3-(5-benzylidene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester
• 英文别名: methyl 3-{5-[(Z)-benzylidene]-5,6-dihydro-2-oxo-2H-pyran-3-yl}propanoate
• CAS: 518358-06-0
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: CBKJUDQDDVSDFT-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Z-3-(5-benzylidene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 14.0h， 以72%的产率得到3-{5-[(Z)-benzylidene]-5,6-dihydro-2-oxo-2H-pyran-3-yl}propanoic acid
  参考文献：
  名称：

  Synthesis and MMP-Inhibitory Activity of Gelastatin Analogues

  摘要：

  Gelastatin A and B, isolated from culture broth of Westerdykella mititispora F 50733, have been reported to exhibit MMP-inhibitory activities at a sub-micromolar level. In an effort to exploit this lead, we synthesized gelastatin analogues in which the conjugated triene unit of natural gelastatins was replaced by the benzylidene group. The (Z)-isomeric synthetic benzylidene-gelastatin exhibited MMP-inhibitory activities comparable to those reported for the natural products. Therefore, this compound appears to be a viable lead in searching for therapeutically useful MMP inhibitors.

  DOI：

  10.1002/1522-2675(200211)85:11<3994::aid-hlca3994>3.0.co;2-2
• 作为产物：
  描述：

  2-{hydroxy-[2-(4-methoxyphenyl)-[1,3]dioxan-5-yl]methyl}acrylic acid methyl ester 在 吡啶 、 4-二甲氨基吡啶 、 palladium diacetate 、 硫酸 、 四丁基氟化铵 、 silver(I) acetate 、 丙酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 268.0h， 生成 Z-3-(5-benzylidene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of arylidene-substituted gelastatin analogues and their screening for MMP-2 inhibitory activity

  摘要：

  A series of arylidene-substituted gelastatin analogues were synthesized in a divergent manner. Each analogue was obtained as a mixture of isomers. Calculation methods were devised to deduce the MMP-2 inhibitory activity of each isomer from the activity of an isomeric mixture and its composition. This protocol is suitable for rapidly generating a variety of arylidene-substituted gelastatin analogues and screening them for highly active inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.037