trans-N-(carboxymethyl)-4-(β-1-naphthylvinyl)pyridinium bromide | 89711-10-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: trans-N-(carboxymethyl)-4-(β-1-naphthylvinyl)pyridinium bromide
• 英文别名: 2-[4-[(E)-2-naphthalen-1-ylethenyl]pyridin-1-ium-1-yl]acetic acid;bromide
• CAS: 89711-10-4
• 化学式: Br*C₁₉H₁₆NO₂
• 分子量: 370.246
• InChiKey: LLWRQHLXMFRHLO-HRNDJLQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  41.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为产物：
  描述：

  1-Ethoxycarbonylmethyl-4-((E)-2-naphthalen-1-yl-vinyl)-pyridinium; bromide 在 氢溴酸 作用下， 反应 0.33h， 以60%的产率得到trans-N-(carboxymethyl)-4-(β-1-naphthylvinyl)pyridinium bromide
  参考文献：
  名称：

  Structural correlations of choline acetyltransferase inhibitors: trans-N-(carboxymethyl)-4-(.beta.-1-naphthylvinyl)pyridinium bromide and cis-N-(2-aminoethyl)-4-(.beta.-1-naphthylvinyl)-3-methylpyridinium bromide hydrobromide

  摘要：

  This paper correlates the X-ray structures of two 4-(beta-1-naphthylvinyl)pyridine analogues (one cis and one trans) with chemical and biological activity data for this class of cholineacetylase inhibitors. Our results suggest that one of the two proposed mechanisms for inhibition by this class of compounds better describes their efficacy. Previous arguments about coplanarity of the aromatic rings and nucleophilicty across the vinyl linkage need to be modified. Quantum calculations are also included and substantiate previous suggestions about the charge distribution across the vinyl linkages. An alternate new mechanism of inhibition is proposed to encompass the published data and more recent results discussed in this paper.

  DOI：

  10.1021/jm00373a002

文献信息

• Structural correlations of choline acetyltransferase inhibitors: trans-N-(carboxymethyl)-4-(.beta.-1-naphthylvinyl)pyridinium bromide and cis-N-(2-aminoethyl)-4-(.beta.-1-naphthylvinyl)-3-methylpyridinium bromide hydrobromide
  作者：Andrew Y. Chweh、John F. DeBernardis、Jerome F. Siuda、Nelson G. Rondan、Jaime E. Abola、Donald J. Abraham

  DOI：10.1021/jm00373a002

  日期：1984.7

  This paper correlates the X-ray structures of two 4-(beta-1-naphthylvinyl)pyridine analogues (one cis and one trans) with chemical and biological activity data for this class of cholineacetylase inhibitors. Our results suggest that one of the two proposed mechanisms for inhibition by this class of compounds better describes their efficacy. Previous arguments about coplanarity of the aromatic rings and nucleophilicty across the vinyl linkage need to be modified. Quantum calculations are also included and substantiate previous suggestions about the charge distribution across the vinyl linkages. An alternate new mechanism of inhibition is proposed to encompass the published data and more recent results discussed in this paper.