4-(3,4-dichloro-phenethyl)-pyridine | 36995-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(3,4-dichloro-phenethyl)-pyridine
• 英文别名: 4-[2-(3,4-Dichlorophenyl)ethyl]pyridine
• CAS: 36995-60-5
• 化学式: C₁₃H₁₁Cl₂N
• 分子量: 252.143
• InChiKey: OVPOUKFDQAESRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(3,4-dichloro-phenethyl)-pyridine 生成 4-[2-(3,4-Dichlorophenyl)ethyl]-1,2,3,6-tetrahydro-1-methylpyridine
  参考文献：
  名称：

  EFANGE, S. M. N.;MICHELSON, R. H.;REMMEL, R. P.;BOUDREAU, R. J.;DUTTA, A.+, J. MED. CHEM., 33,(1990) N2, C. 3133-3138

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二氯苯甲醛 在 palladium on activated charcoal 氢气 、 乙酸酐 作用下， 以 乙醇 为溶剂， 反应 45.0h， 生成 4-(3,4-dichloro-phenethyl)-pyridine
  参考文献：
  名称：

  Flexible N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analog: synthesis and monoamine oxidase catalyzed bioactivation

  摘要：

  Eighteen analogues of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) were synthesized and evaluated as substrates of monoamine oxidase. In general, the flexible analogues, characterized by the presence of a methylene (or ethylene) bridge between the aryl/heteroaryl and tetrahydropyridyl moieties, were better substrates of the enzyme than the conformationally restricted MPTP. It is suggested that the increased oxidative activity of these flexible analogues reflects enhanced binding due to the ability of the C-4-aryl/heteroaryl substituent to gain access to a hydrophobic pocket within the substrate binding site.

  DOI：

  10.1021/jm00174a007

文献信息

• EFANGE, S. M. N.;MICHELSON, R. H.;REMMEL, R. P.;BOUDREAU, R. J.;DUTTA, A.+, J. MED. CHEM., 33,(1990) N2, C. 3133-3138
  作者：EFANGE, S. M. N.、MICHELSON, R. H.、REMMEL, R. P.、BOUDREAU, R. J.、DUTTA, A.+

  DOI：——

  日期：——
• SUBSTITUTED IMIDAZOLES HAVING ANTI-CANCER AND CYTOKINE INHIBITORY ACTIVITY
  申请人：MERCK & CO., INC.

  公开号：EP0854870A1

  公开（公告）日：1998-07-29
• EP0854870A4
  申请人：——

  公开号：EP0854870A4

  公开（公告）日：1999-01-07
• [EN] SUBSTITUTED IMIDAZOLES HAVING ANTI-CANCER AND CYTOKINE INHIBITORY ACTIVITY<br/>[FR] IMIDAZOLES SUBSTITUES AYANT UNE ACTIVITE ANTICANCEREUSE ET INHIBITRICE DE CYTOKINE
  申请人：——

  公开号：WO1997012876A1

  公开（公告）日：1997-04-10

  [EN] Compounds represented by formula (I), are disclosed. represents an aromatic group containing 6-10 atoms; and (a) represents a 4 to 10 membered non-aromatic heterocycle containing at least one N atom, and optionally containing 1-2 additional N atoms and 0-1 O or S atom. A pharmaceutical composition is also included. Methods of treating cancer and cytokine mediated diseases are also included.
  [FR] L'invention porte sur des composés représentés par la formule (I), dans laquelle représente un groupe aromatique contenant de 6 à 10 atomes; et (a) représente un hétérocycle non-aromatique de 4 à 10 chaînons contenant au moins un atome N, et contenant facultativement de 1 à 2 atomes N supplémentaires et de 0 à 1 atome O ou S. L'invention porte également sur une composition pharmaceutique, et sur des méthodes de traitement du cancer et de maladies véhiculées par la cytokine.
• Flexible N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analog: synthesis and monoamine oxidase catalyzed bioactivation
  作者：S. Mbera Ngale Efange、R. H. Michelson、R. P. Remmel、R. J. Boudreau、A. K. Dutta、A. Freshler

  DOI：10.1021/jm00174a007

  日期：1990.12

  Eighteen analogues of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) were synthesized and evaluated as substrates of monoamine oxidase. In general, the flexible analogues, characterized by the presence of a methylene (or ethylene) bridge between the aryl/heteroaryl and tetrahydropyridyl moieties, were better substrates of the enzyme than the conformationally restricted MPTP. It is suggested that the increased oxidative activity of these flexible analogues reflects enhanced binding due to the ability of the C-4-aryl/heteroaryl substituent to gain access to a hydrophobic pocket within the substrate binding site.