3-(3-bromophenyl)-2-hydroxy-1-[1-(4-phenylpiperidinyl)]propane | 145233-28-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(3-bromophenyl)-2-hydroxy-1-[1-(4-phenylpiperidinyl)]propane
• 英文别名: 1-(3-Bromo-phenyl)-3-(4-phenyl-piperidin-1-yl)-propan-2-ol；1-(3-bromophenyl)-3-(4-phenylpiperidin-1-yl)propan-2-ol
• CAS: 145233-28-9
• 化学式: C₂₀H₂₄BrNO
• 分子量: 374.321
• InChiKey: ANCSSFCYCYJZLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3-(3-bromophenyl)-2-hydroxy-1-[1-(4-phenylpiperidinyl)]propane 在 三乙胺 作用下， 生成 Acetic acid 1-(3-bromo-benzyl)-2-(4-phenyl-piperidin-1-yl)-ethyl ester
  参考文献：
  名称：

  Acyclic analogs of 2-(4-phenylpiperidino)cyclohexanol (vesamicol): conformationally mobile inhibitors of vesicular acetylcholine transport

  摘要：

  Several 1,3-disubstituted propan-2-ols and one alpha,beta-disubstituted ethanol (11i) were synthesized and evaluated as potential acyclic mimics of the vesicular acetylcholine transport inhibitor 2-(4-phenylpiperidinyl)cyclohexanol (1, vesamicol, AH5183). Analogues containing the 4-phenylpiperidyl fragment (11a, 11b) were more potent than those containing the 4-phenylpiperazyl moiety (11e, 11f). Substitution at the second terminal carbon of the propyl (or ethyl) fragment with simple lipophilic aryl substituents yielded potent inhibitors of vesicular acetylcholine storage, including (-)-11a and d-11i, which are equipotent with vesamicol. However, the activity of analogues containing bicyclic aryl groups was susceptible to aryl substitution patterns (11g vs 11h), indicating a definite receptor site topography. In addition, the inhibitory activity of these acyclic analogues was enantioselective, exhibiting a preference, similar to the parent vesamicol, for the levorotatory isomer [(-)-11a vs (+)-11a]. Therefore, the simple lipophilic acyclic vicinal amino alcohols may successfully mimic the biological activity of vesamicol.

  DOI：

  10.1021/jm00112a044
• 作为产物：
  描述：

  1-烯丙基-3-溴苯 在 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 3-(3-bromophenyl)-2-hydroxy-1-[1-(4-phenylpiperidinyl)]propane
  参考文献：
  名称：

  Acyclic analogs of 2-(4-phenylpiperidino)cyclohexanol (vesamicol): conformationally mobile inhibitors of vesicular acetylcholine transport

  摘要：

  Several 1,3-disubstituted propan-2-ols and one alpha,beta-disubstituted ethanol (11i) were synthesized and evaluated as potential acyclic mimics of the vesicular acetylcholine transport inhibitor 2-(4-phenylpiperidinyl)cyclohexanol (1, vesamicol, AH5183). Analogues containing the 4-phenylpiperidyl fragment (11a, 11b) were more potent than those containing the 4-phenylpiperazyl moiety (11e, 11f). Substitution at the second terminal carbon of the propyl (or ethyl) fragment with simple lipophilic aryl substituents yielded potent inhibitors of vesicular acetylcholine storage, including (-)-11a and d-11i, which are equipotent with vesamicol. However, the activity of analogues containing bicyclic aryl groups was susceptible to aryl substitution patterns (11g vs 11h), indicating a definite receptor site topography. In addition, the inhibitory activity of these acyclic analogues was enantioselective, exhibiting a preference, similar to the parent vesamicol, for the levorotatory isomer [(-)-11a vs (+)-11a]. Therefore, the simple lipophilic acyclic vicinal amino alcohols may successfully mimic the biological activity of vesamicol.

  DOI：

  10.1021/jm00112a044

文献信息

• RADIOPHARMACEUTICAL AGENTS FOR THE DETECTION OF ALZHEIMER'S DISEASE
  申请人：THE REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：EP0576611A1

  公开（公告）日：1994-01-05
• EP0576611A4
  申请人：——

  公开号：EP0576611A4

  公开（公告）日：1996-01-24
• US5358712A
  申请人：——

  公开号：US5358712A

  公开（公告）日：1994-10-25
• US5721243A
  申请人：——

  公开号：US5721243A

  公开（公告）日：1998-02-24
• [EN] RADIOPHARMACEUTICAL AGENTS FOR THE DETECTION OF ALZHEIMER'S DISEASE
  申请人：THE REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：WO1992016239A1

  公开（公告）日：1992-10-01

  (EN) Novel anticholinergics which are related to vesamicol are particularly useful when radiolabeled for evaluating cholinergic innervation in the living human brain. The cholinergic deficit in the Alzheimer's brain should be identifiable with these radioligands.(FR) De nouveaux anticholinergiques qui sont apparentés au vésamisol sont particulièrement utiles lorsqu'ils sont radiomarqués afin d'évaluer l'innervation cholinergique dans le cerveau d'un être humain vivant. Le déficit cholinergique dans le cerveau atteint de la maladie d'alzheimer pourrait être identifié avec ces radioligands.