ethyl α-3-butynyl-3-pyridylacetate | 145475-81-6

• 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: ethyl α-3-butynyl-3-pyridylacetate
• 英文别名: Ethyl 2-pyridin-3-ylhex-5-ynoate
• CAS: 145475-81-6
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: ZFHNBMVSAMARHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl α-3-butynyl-3-pyridylacetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以86%的产率得到α-3-butynyl-3-pyridylacetic acid
  参考文献：
  名称：

  Structural determinants of haloenol lactone-mediated suicide inhibition of canine myocardial calcium-independent phospholipase A2

  摘要：

  Haloenol lactones are potent mechanism im-based inhibitors of a novel class of calcium-independent phospholipases A2 Which have been implicated as the enzymic mediators of membrane dysfunction during myocardial ischemia (Hazen, S. L.; et al. J. Biol. Chem. 1991, 266,7227-7232). Herein we demonstrate that the ring size, hydrophobic group, and cryptic electrophile in the haloenol lactone moiety are important and modifiable determinants of the inhibitory potency of haloenol lactone-mediated inhibition of calcium-independent phospholipase A2. Direct comparisons between haloenol lactone-mediated inhibition of calcium-independent phospholipase A2 and the absence of inhibition with calcium-dependent phospholipase A2 further underscore the marked differences in the catalytic strategy employed by these two classes of intracellular phospholipases A2.

  DOI：

  10.1021/jm00053a012
• 作为产物：
  描述：

  3-吡啶乙酸乙酯 、 but-3-yn-1-yl trifluoromethanesulfonate 在 lithium diisopropyl amide 作用下， 生成 ethyl α-3-butynyl-3-pyridylacetate
  参考文献：
  名称：

  Structural determinants of haloenol lactone-mediated suicide inhibition of canine myocardial calcium-independent phospholipase A2

  摘要：

  Haloenol lactones are potent mechanism im-based inhibitors of a novel class of calcium-independent phospholipases A2 Which have been implicated as the enzymic mediators of membrane dysfunction during myocardial ischemia (Hazen, S. L.; et al. J. Biol. Chem. 1991, 266,7227-7232). Herein we demonstrate that the ring size, hydrophobic group, and cryptic electrophile in the haloenol lactone moiety are important and modifiable determinants of the inhibitory potency of haloenol lactone-mediated inhibition of calcium-independent phospholipase A2. Direct comparisons between haloenol lactone-mediated inhibition of calcium-independent phospholipase A2 and the absence of inhibition with calcium-dependent phospholipase A2 further underscore the marked differences in the catalytic strategy employed by these two classes of intracellular phospholipases A2.

  DOI：

  10.1021/jm00053a012

文献信息

• US5208244A
  申请人：——

  公开号：US5208244A

  公开（公告）日：1993-05-04