1-bromo-3-[4-[(E)-2-naphthalen-1-ylethenyl]pyridin-1-ium-1-yl]propan-2-one;bromide | 110852-64-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-bromo-3-[4-[(E)-2-naphthalen-1-ylethenyl]pyridin-1-ium-1-yl]propan-2-one;bromide
• CAS: 110852-64-7
• 化学式: Br*C₂₀H₁₇BrNO
• 分子量: 447.169
• InChiKey: FCFOWYGVLQCUSB-HRNDJLQDSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  21
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-bromo-3-[4-[(E)-2-naphthalen-1-ylethenyl]pyridin-1-ium-1-yl]propan-2-one;bromide 在 乙醇 作用下， 以13%的产率得到1-(3-Hydroxy-2-oxo-propyl)-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
• 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-bromo-3-[4-[(E)-2-naphthalen-1-ylethenyl]pyridin-1-ium-1-yl]propan-2-one;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.