1-Ethoxycarbonylmethyl-4-((E)-2-naphthalen-1-yl-vinyl)-pyridinium; bromide | 110852-61-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-Ethoxycarbonylmethyl-4-((E)-2-naphthalen-1-yl-vinyl)-pyridinium; bromide
• 英文别名: ethyl 2-[4-[(E)-2-naphthalen-1-ylethenyl]pyridin-1-ium-1-yl]acetate;bromide
• CAS: 110852-61-4
• 化学式: Br*C₂₁H₂₀NO₂
• 分子量: 398.299
• InChiKey: QDNWCUSIJSRTFB-ASTDGNLGSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-萘甲醛 在 乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 1-Ethoxycarbonylmethyl-4-((E)-2-naphthalen-1-yl-vinyl)-pyridinium; bromide
  参考文献：
  名称：

  Evaluation of the side arm of (naphthylvinyl)pyridinium inhibitors of choline acetyltransferase

  摘要：

  A number of quaternary salts of trans-4-(beta-1-naphthylvinyl)pyridine (NVP) were synthesized and evaluated as inhibitors of the enzymes choline acetyltransferase (ChAT) and acetylcholinesterase (AChE). Structural variations in the side arm attached to the pyridine nitrogen atom demonstrate that an inductive effect is small but significant for activity. Inhibition of ChAT by alkylated derivatives decreases when electron-withdrawing groups are placed in the side chain. Substitution of a methyl group on the pyridine ring only slightly affects activities toward ChAT and AChE. When the pyridinium moiety is replaced by an imidazolium ring, no ChAT inhibition was observed. The imidazolium compound, however, was a weak inhibitor of AChE. For design of affinity columns for purification of ChAT, the data also supports the use of long chain alkylated amide derivatives of NVP.

  DOI：

  10.1021/jm00396a017

文献信息

• DEBERNARDIS, J. F.;GIFFORD, P.;RIZK, M.;ERTEL, R.;ABRAHAM, D. J.;SIUDA, J+, J. MED. CHEM., 31,(1988) N 1, 117-121
  作者：DEBERNARDIS, J. F.、GIFFORD, P.、RIZK, M.、ERTEL, R.、ABRAHAM, D. J.、SIUDA, J+

  DOI：——

  日期：——
• Evaluation of the side arm of (naphthylvinyl)pyridinium inhibitors of choline acetyltransferase
  作者：J. F. DeBernardis、P. Gifford、M. Rizk、R. Ertel、D. J. Abraham、J. F. Siuda

  DOI：10.1021/jm00396a017

  日期：1988.1

  A number of quaternary salts of trans-4-(beta-1-naphthylvinyl)pyridine (NVP) were synthesized and evaluated as inhibitors of the enzymes choline acetyltransferase (ChAT) and acetylcholinesterase (AChE). Structural variations in the side arm attached to the pyridine nitrogen atom demonstrate that an inductive effect is small but significant for activity. Inhibition of ChAT by alkylated derivatives decreases when electron-withdrawing groups are placed in the side chain. Substitution of a methyl group on the pyridine ring only slightly affects activities toward ChAT and AChE. When the pyridinium moiety is replaced by an imidazolium ring, no ChAT inhibition was observed. The imidazolium compound, however, was a weak inhibitor of AChE. For design of affinity columns for purification of ChAT, the data also supports the use of long chain alkylated amide derivatives of NVP.
• 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.