2-Brom-5-(methylthio)-benzoesaeure | 22362-40-9

• 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: 2-Brom-5-(methylthio)-benzoesaeure
• 英文别名: 2-Bromo-5-(methylthio)benzoic acid；2-bromo-5-methylsulfanylbenzoic acid
• CAS: 22362-40-9
• 化学式: C₈H₇BrO₂S
• 分子量: 247.112
• InChiKey: WJGFDDCMTMHZMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Brom-5-(methylthio)-benzoesaeure 在 氢氧化钾 、 铜 、 红铝 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (5-Methylsulfanyl-2-phenylsulfanyl-phenyl)-acetonitrile
  参考文献：
  名称：

  Potential antipsychotics: 2-Methoxy, 2-methylthio-, 2-(dimethylsulfamoyl)- and 2-trifluoromethyl-10-piperazinodibenzo[b,f]thiepins

  摘要：

  DOI：

  10.1135/cccc19751940

文献信息

• Synthesis and Pharmacological Evaluation of <i>N</i>-(2,5-Disubstituted phenyl)-<i>N</i>‘-(3-substituted phenyl)-<i>N</i>‘-methylguanidines As <i>N</i>-Methyl-<scp>d</scp>-aspartate Receptor Ion-Channel Blockers
  作者：Lain-Yen Hu、Junqing Guo、Sharad S. Magar、James B. Fischer、Kathleen J. Burke-Howie、Graham J. Durant

  DOI：10.1021/jm970459c

  日期：1997.12.1

  In the mammalian central nervous system, the N-methyl-D-aspartate (NMDA) subclass of glutamate receptors may play an important role in brain diseases such as stroke, brain or spinal cord trauma, epilepsy, and certain neurodegenerative diseases. Compounds which specifically antagonize the actions of the neurotransmitter glutamate at the NMDA receptor ion-channel site offer a novel approach to treating these disorders. CERESTAT (4, aptiganel CNS 1102) is currently undergoing clinical trial for the treatment of traumatic brain injury and stroke. Previously, we reported that analogues of N-1-naphthyl-N'-(3-ethylphenyl)-N'-methylguanidine (4) bound to the NMDA receptor ion-channel site with high potency and selectivity. Recently, molecules active at both a receptors and NMDA receptor sites were investigated. A series of substituted diphenylguanidines 6 which are structurally related to N-1-naphthyl-N'-(3-ethylphenyl)-N'-methylguanidine was prepared. Compounds containing appropriate substitution pattern in one of the phenyl rings of diphenylguanidines displayed high affinity. For example, N-(2,5-dibromophenyl)-N'-(3-ethylphenyl)-N'-methylguanidine (27b, R-2 = R-5 = Br, R-3 = C2H5) exhibited potency at both a receptors and NMDA receptor sites; 27b also showed high efficacy in vivo in a neonatal rat excitotoxicity model. Further studies indicated that substituent effects were important in this compound series, and 2,5-disubstituted phenyl was the preferred substitution pattern for high-affinity binding at NMDA receptor sites. Bromo and methylthio were the optimal substituents for the R-2 and R-5 positions of the 2,5-disubstituted phenyl group, respectively. N-(2-Bromo-5-(methylthio)phenyl)-N'-(3-ethylphenyl)- N'-methylguanidine (34b, R-2 = Br, R-5 = SMe, R-3 = C2H5) was highly active at NMDA receptor sites. We found that the binding affinity of guanidines of type 6 could be further enhanced with the appropriate substitution at R-3. Optimal activity in this series are afforded by 43b and 44b (R-2 = Cl or Br, R-5 = R-3 = SCH3). Both 43b and 44b bound to NMDA receptor sites with high potency and selectivity (K-i vs [H-3]MK-801: 1.87 and 1.65 nM, respectively); these compounds are active in vivo in various animal models of neuroprotection. The structure-activity relationships for-these compounds at the NMDA receptor ion-channel site are discussed.
• SINDELAR K.; DLABAC A.; METYSOVA J.; KAKAC B.; HOLUBEK J.; SVATEK E.; SED+, COLLECT. CHEM. COMMUNS <CCCC-AK>, 1975, 40, NO 6, 1940-1959
  作者：SINDELAR K.、 DLABAC A.、 METYSOVA J.、 KAKAC B.、 HOLUBEK J.、 SVATEK E.、 SED+

  DOI：——

  日期：——
• THERAPEUTIC SUBSTITUTED GUANIDINES
  申请人：CeNes Limited

  公开号：EP0705100B1

  公开（公告）日：2003-07-30
• US6147063A
  申请人：——

  公开号：US6147063A

  公开（公告）日：2000-11-14
• US6153604A
  申请人：——

  公开号：US6153604A

  公开（公告）日：2000-11-28