tetrahydro (E)-6-(iodomethylene)-3-(1-naphthalenyl)-2H-pyran-2-one | 88070-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tetrahydro (E)-6-(iodomethylene)-3-(1-naphthalenyl)-2H-pyran-2-one
• 英文别名: (E)-6-Iodomethylene-3-naphthalen-1-yl-tetrahydro-pyran-2-one；(6E)-6-(iodomethylidene)-3-naphthalen-1-yloxan-2-one
• CAS: 88070-99-9
• 化学式: C₁₆H₁₃IO₂
• 分子量: 364.183
• InChiKey: ZJGPRRLHNMNINO-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tetrahydro (E)-6-(iodomethylene)-3-(1-naphthalenyl)-2H-pyran-2-one 在 bis(triphenylphosphine)palladium(II)-chloride 、 silver nitrate 、 三乙胺 、 copper(l) chloride 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 tetrahydro-3-(1-naphthalenyl)-(E)-6-(prop-2-ynylidene)-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：

  2-(1-naphthyl)-5-hexynoic acid 在 碘 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 50.0h， 以5%的产率得到tetrahydro-(Z)-6-(iodomethylene)-3-(1-naphthalenyl)-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

文献信息

• Process for preparing purified s-bel and r-bel and compositions thereof
  申请人：Gross W Richard

  公开号：US20050181496A1

  公开（公告）日：2005-08-18

  A process for resolution of racemic BEL into its individual enantiomeric constituents by chiral HPLC. A method for determining the role of specific isoforms of iPLA 2 in biologic processes.

  一种通过手性高效液相色谱法将外消旋 BEL 分解为单个对映体成分的工艺。一种确定 iPLA 特定异构体作用的方法 2 在生物过程中的作用的方法。
• US5208244A
  申请人：——

  公开号：US5208244A

  公开（公告）日：1993-05-04
• US7741344B2
  申请人：——

  公开号：US7741344B2

  公开（公告）日：2010-06-22
• [EN] PROCESS FOR PREPARING PURIFIED S-BEL AND R-BEL AND COMPOSITIONS THEREOF<br/>[FR] PROCEDE DE PREPARATION DE BEL S ET DE BEL R PURIFIES ET LEURS COMPOSITIONS
  申请人：UNIV ST LOUIS

  公开号：WO2003079996A2

  公开（公告）日：2003-10-02

  A process for resolution of racemic BEL into its individual enantiomeric constituents by chiral HPLC. A method for determining the role of specific isoforms of iPLA2 in biologic processes.
• 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.