1-bromo-2-[bis(4-chlorophenyl)methoxy]ethane | 221916-05-8

• 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: 1-bromo-2-[bis(4-chlorophenyl)methoxy]ethane
• 英文别名: 2-[bis(4-chlorophenyl)methoxy]ethyl bromide；1-[2-bromoethoxy-(4-chlorophenyl)methyl]-4-chlorobenzene
• CAS: 221916-05-8
• 化学式: C₁₅H₁₃BrCl₂O
• 分子量: 360.078
• InChiKey: ZKLLZRSEVMGSGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-bromo-2-[bis(4-chlorophenyl)methoxy]ethane 在 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 33.0h， 生成 1-<2-ethyl>-N-methyl-3-piperidinecarboxamide
  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
• 作为产物：
  描述：

  4,4'-二氯二苯甲醇 、 2-溴乙醇 在 硫酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 1-bromo-2-[bis(4-chlorophenyl)methoxy]ethane
  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

• Trifluoromethyl ketone analogs as selective cPLA2 inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US06350892B1

  公开（公告）日：2002-02-26

  Selective inhibitors of the cPLA2 enzymes are provided which are of use in controlling a wide variety of inflammatory diseases. The inhibitors of the present invention have the general formula where (R′), p, D, Y, Z, Ra, Rb and A are as defined in the specification.

  本发明提供了选择性cPLA2酶抑制剂，可用于控制各种炎症性疾病。本发明的抑制剂具有一般公式，其中(R′)、p、D、Y、Z、Ra、Rb和A如规范中定义。
• Synthesis and dopamine transporter binding affinities of 3α-Benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes
  作者：Amy L Bradley、Sari Izenwasser、Dean Wade、Cheryl Klein-Stevens、Naijue Zhu、Mark L Trudell

  DOI：10.1016/s0960-894x(02)00464-x

  日期：2002.9

  A series of 3alpha-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes was synthesized and the binding affinities of the compounds were determined at the dopamine transporter. The unsubstituted analogue 7b (K-i = 98 nM) was the most potent compound of the series with binding affinity three-times greater than cocaine and only 5-fold less than GBR-12909. The structure-activity data for 7a-f suggests that these compounds may be binding at the dopamine transporter in a similar fashion to GBR 12909. (C) 2002 Elsevier Science Ltd. All rights reserved.
• EP1140791A4
  申请人：——

  公开号：EP1140791A4

  公开（公告）日：2001-10-10
• SELECTIVE CPLA 2 INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP1140791A2

  公开（公告）日：2001-10-10
• US6255496B1
  申请人：——

  公开号：US6255496B1

  公开（公告）日：2001-07-03