4-(2-Bromo-phenylsulfanyl)-3-trifluoromethyl-benzaldehyde | 387873-59-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(2-Bromo-phenylsulfanyl)-3-trifluoromethyl-benzaldehyde
• 英文别名: 4-(2-Bromophenyl)sulfanyl-3-(trifluoromethyl)benzaldehyde
• CAS: 387873-59-8
• 化学式: C₁₄H₈BrF₃OS
• 分子量: 361.182
• InChiKey: PEIZECJCCRGTRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-Bromo-phenylsulfanyl)-3-trifluoromethyl-benzaldehyde 在 sodium hydroxide 、 tris(dibenzylideneacetone)dipalladium (0) 、 sodium hydride 、 1-羟基苯并三唑 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.0h， 生成 (1S,2S)-2-[4-(2-Piperidin-1-yl-phenylsulfanyl)-3-trifluoromethyl-phenyl]-cyclopropanecarboxylic acid [3-(2-oxo-pyrrolidin-1-yl)-propyl]-amide
  参考文献：
  名称：

  Discovery and SAR of diarylsulfide cyclopropylamide LFA-1/ICAM-1 interaction antagonists

  摘要：

  Diarylsulfide cyclopropylamides were synthesized and evaluated as LFA-1/ICAM-1 interaction antagonists. A substituent pattern was identified which maximized potency and minimized protein binding as exemplified by antagonist 30 (IC50 = 5 nM). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00105-6
• 作为产物：
  描述：

  2-溴硫代苯酚 、 Trifluoro-methanesulfonic acid 4-formyl-2-trifluoromethyl-phenyl ester 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.42h， 生成 4-(2-Bromo-phenylsulfanyl)-3-trifluoromethyl-benzaldehyde
  参考文献：
  名称：

  Discovery and SAR of diarylsulfide cyclopropylamide LFA-1/ICAM-1 interaction antagonists

  摘要：

  Diarylsulfide cyclopropylamides were synthesized and evaluated as LFA-1/ICAM-1 interaction antagonists. A substituent pattern was identified which maximized potency and minimized protein binding as exemplified by antagonist 30 (IC50 = 5 nM). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00105-6

文献信息

• Aryl phenylcyclopropyl sulfide derivatives and their use as cell adhesion inhibiting anti-inflammatory and immune suppressive agents
  申请人：——

  公开号：US20020156314A1

  公开（公告）日：2002-10-24

  The present invention relates to novel cyclopropane-containing diaryl sulfide compounds that are useful for treating inflammatory and immune diseases, to pharmaceutical compositions comprising these compounds, and to methods of inhibiting inflammation or suppressing immune response in a mammal.

  本发明涉及可用于治疗炎症和免疫疾病的新型含环丙烷二芳基硫醚化合物，涉及包含这些化合物的药物组合物，还涉及抑制哺乳动物炎症或抑制免疫反应的方法。
• US6521619B2
  申请人：——

  公开号：US6521619B2

  公开（公告）日：2003-02-18
• Discovery and SAR of diarylsulfide cyclopropylamide LFA-1/ICAM-1 interaction antagonists
  作者：James T. Link、Bryan Sorensen、Gang Liu、Zhonghua Pei、Edward B. Reilly、Sandra Leitza、Greg Okasinski

  DOI：10.1016/s0960-894x(01)00105-6

  日期：2001.4

  Diarylsulfide cyclopropylamides were synthesized and evaluated as LFA-1/ICAM-1 interaction antagonists. A substituent pattern was identified which maximized potency and minimized protein binding as exemplified by antagonist 30 (IC50 = 5 nM). (C) 2001 Elsevier Science Ltd. All rights reserved.