NMB | 1297395-44-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: NMB
• 英文别名: 2-nitro-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenyl 4-(methoxycarbonyl-1-butynyl)benzoate；4-(5-Methoxy-5-oxo-1-pentynyl)benzoic acid 2-nitro-4-[3-(trifluoromethyl)-3H-diazirine-3-yl]phenyl ester；[2-nitro-4-[3-(trifluoromethyl)diazirin-3-yl]phenyl] 4-(5-methoxy-5-oxopent-1-ynyl)benzoate
• CAS: 1297395-44-8
• 化学式: C₂₁H₁₄F₃N₃O₆
• 分子量: 461.354
• InChiKey: XCBVGMDMZTWMJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3-(4-methoxyphenyl)-3-(trifluoromethyl)-3H-diazirine 在 4-二甲氨基吡啶 、 硝酸 、 三溴化硼 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸酐 、 甲苯 为溶剂， 反应 96.5h， 生成 NMB
  参考文献：
  名称：

  A photoreactive probe that differentiates the binding sites of noncompetitive GABA receptor antagonists

  摘要：

  gamma-Aminobutyric acid (GABA) receptors are postsynaptic membrane protein complexes that are important not only in the regulation of the nervous system but also as targets of drugs and insecticides. We synthesized a photoreactive straight-chain noncompetitive antagonist (NCA), 2-nitro-4-[3-(trifluoromethyl)3H- diazirin-3-yl]phenyl 4-(4-methoxycarbonyl-1-butynyl)benzoate (NMB), to probe the NCA binding site. Our data show that this probe labels the NCA site and demonstrate that the NCA insecticide fipronil binds at a site distinct from that of other NCAs, such as picrotoxinin and 4'-ethynyl-4-n-propyl-bicycloorthobenzoate. The unique molecule NMB will be useful in identifying the cross-linking site of straight-chain NCAs in GABA receptors and mapping allosteric binding sites. Such studies should provide invaluable information in designing novel NCAs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.118

文献信息

• A photoreactive probe that differentiates the binding sites of noncompetitive GABA receptor antagonists
  作者：Hiroshi Shimotahira、Sayaka Fusazaki、Izumi Ikeda、Yoshihisa Ozoe

  DOI：10.1016/j.bmcl.2011.01.118

  日期：2011.3

  gamma-Aminobutyric acid (GABA) receptors are postsynaptic membrane protein complexes that are important not only in the regulation of the nervous system but also as targets of drugs and insecticides. We synthesized a photoreactive straight-chain noncompetitive antagonist (NCA), 2-nitro-4-[3-(trifluoromethyl)3H- diazirin-3-yl]phenyl 4-(4-methoxycarbonyl-1-butynyl)benzoate (NMB), to probe the NCA binding site. Our data show that this probe labels the NCA site and demonstrate that the NCA insecticide fipronil binds at a site distinct from that of other NCAs, such as picrotoxinin and 4'-ethynyl-4-n-propyl-bicycloorthobenzoate. The unique molecule NMB will be useful in identifying the cross-linking site of straight-chain NCAs in GABA receptors and mapping allosteric binding sites. Such studies should provide invaluable information in designing novel NCAs. (C) 2011 Elsevier Ltd. All rights reserved.