α-3-butynylphenoxyacetic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-3-butynylphenoxyacetic acid
• 英文别名: alpha-(3-Butynyl)phenoxyacetic acid；2-phenoxyhex-5-ynoic acid
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: FREWHVPCHJANMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-3-butynylphenoxyacetic acid 在 四丁基氢氧化铵 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以6%的产率得到(E)-6-(bromomethylene)tetrahydro-3-phenoxy-2H-pyran-2-one
  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：

  4-溴-1-丁炔 、 苯氧乙酸 在 lithium diisopropyl amide 作用下， 生成 α-3-butynylphenoxyacetic 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

文献信息

• Method of selectively inhibiting calcium-independent myocardial
  申请人：Washington University

  公开号：US05208244A1

  公开（公告）日：1993-05-04

  Inhibition of calcium-independent myocardial phospholipase A.sub.2 is shown for compounds of the formula: ##STR1## wherein R and R.sup.1 independently represent hydrogen and halogen, alkyl, alkenyl and alkynyl radicals; R.sup.2 represents aryl, aryloxy, and heteroaryl radicals; and X is 1 or 2.

  该公式的化合物显示了对无钙心肌磷脂酶A.sub.2的抑制作用: ## STR1 ## 其中R和R.sup.1独立地表示氢和卤素，烷基，烯基和炔基基团; R.sup.2表示芳基，芳氧基和杂环芳基基团; X为1或2。
• US5208244A
  申请人：——

  公开号：US5208244A

  公开（公告）日：1993-05-04
• Structural determinants of haloenol lactone-mediated suicide inhibition of canine myocardial calcium-independent phospholipase A2
  作者：Lori A. Zupan、Randy H. Weiss、Stanley L. Hazen、Barry L. Parnas、Karl W. Aston、Patrick J. Lennon、Daniel P. Getman、Richard W. Gross

  DOI：10.1021/jm00053a012

  日期：1993.1

  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.