4,4'-dichloro-3-trifluoromethylbenzhydrol | 65430-19-5

• 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: 4,4'-dichloro-3-trifluoromethylbenzhydrol
• 英文别名: (4-Chlorophenyl)-[4-chloro-3-(trifluoromethyl)phenyl]methanol
• CAS: 65430-19-5
• 化学式: C₁₄H₉Cl₂F₃O
• 分子量: 321.126
• InChiKey: APWGDJFHJJSQBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-dichloro-3-trifluoromethylbenzhydrol 在 lithium hydroxide 、 硫酸 、 potassium carbonate 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 81.0h， 生成 1-{2-[(4-Chloro-phenyl)-(4-chloro-3-trifluoromethyl-phenyl)-methoxy]-ethyl}-piperidine-3-carboxylic acid
  参考文献：
  名称：

  Structure-activity studies on benzhydrol-containing nipecotic acid and guvacine derivatives as potent, orally-active inhibitors of GABA uptake

  摘要：

  The introduction of lipophilic groups onto the ring nitrogen of nipecotic acid and guvacine, two known GABA uptake inhibitors, afforded potent, orally-active anticonvulsant drugs. A series of compounds is reported which explores the structure-activity relationships (SAR) in this series. Among the areas explored: side-chain SAR (aromatic-, heterocyclic-, and tricyclic-containing side chains) and modifications to the tetrahydropyridine ring. The benzhydrol ether-containing side chains afforded the most potent compounds with several exhibiting in vitro IC50 values for GABA uptake of <1 muM (including 5, Table 1; 37, 43, Table IV; and 44, Table V). Compound 44 was selected for extensive evaluation and subsequently progressed to Phase 1 clinical trials with severe adverse effects seen after single dose administration to humans.

  DOI：

  10.1021/jm00100a032

文献信息

• Acetic acid derivatives
  申请人：Imperial Chemical Industries Limited

  公开号：US04205087A1

  公开（公告）日：1980-05-27

  Novel di-(substituted phenyl)methoxy acetic acids, alkyl homologues and related salts, ester and amides thereof, together with processes for their manufacture, and pharmaceutical compositions. A representative compound is di-(4-chlorophenyl)methyloxy acetic acid. The compounds possess anti-arthritic properties and in some cases, in addition, an effect on a factor involved in atherosclerotic disease.

  新型二-(取代苯基)甲氧基乙酸，烷基同系物及相关盐、酯和酰胺，以及其制备方法和药物组合物。代表性化合物是二-(4-氯苯基)甲氧基乙酸。这些化合物具有抗关节炎性能，并在某些情况下，还对涉及动脉粥样硬化疾病的因素产生影响。
• US4205087A
  申请人：——

  公开号：US4205087A

  公开（公告）日：1980-05-27