2,5-二氯苄胺 | 10224-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,5-二氯苄胺
• 英文名称: 2,5-dichloro-N-methyl-aniline
• 英文别名: 2,5-Dichlor-N-methyl-anilin；(2,5-dichlorophenyl)methylamine；2,5-dichloro-N-methylaniline
• CAS: 10224-70-1
• 化学式: C₇H₇Cl₂N
• mdl: MFCD11150702
• 分子量: 176.045
• InChiKey: NENSBLLVKCAPRI-UHFFFAOYSA-N

物化性质

• 沸点：
  74-76 °C0.1 mm Hg(lit.)
• 密度：
  1.3172 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  T
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R25,R34
• 危险品运输编号：
  UN 2922 8/PG 3
• WGK Germany：
  3
• 海关编码：
  2921420090

反应信息

• 作为反应物：
  描述：

  2,5-二氯苄胺 在 盐酸 、 sodium nitrite 作用下， 生成 2,5-dichloro-N-methyl-N-nitroso-aniline
  参考文献：
  名称：

  Buelow; Neber, Chemische Berichte, 1916, vol. 49, p. 2195

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(2,5-二氯苯基)甲酰胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 2,5-二氯苄胺
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of N-(2,5-Disubstituted phenyl)-N‘-(3-substituted phenyl)-N‘-methylguanidines As N-Methyl-d-aspartate Receptor Ion-Channel Blockers

  摘要：

  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.

  DOI：

  10.1021/jm970459c

文献信息

• DERIVATIVES OF AZAINDAZOLE OR DIAZAINDAZOLE TYPE AS MEDICAMENT
  申请人：PIERRE FABRE MEDICAMENT

  公开号：US20130085144A1

  公开（公告）日：2013-04-04

  The present invention relates to a compound of following formula (I): or a pharmaceutically acceptable salt or solvate of same, a tautomer of same, or a stereoisomer or mixture of stereoisomers of same in any proportions, such as a mixture of enantiomers, notably a racemic mixture; as well as to the use of same as a drug, notably intended for the treatment of cancer, inflammation and neurodegenerative diseases such as Alzheimer's disease; to the use of same as a kinase inhibitor; to the pharmaceutical compositions comprising same; and to methods for the preparation of same.

  本发明涉及以下式（I）的化合物： 或其药学上可接受的盐或溶剂，同分异构体，立体异构体或同分异构体的混合物，比如对映体混合物，尤其是消旋混合物；以及将其用作药物，尤其是用于治疗癌症、炎症和神经退行性疾病如阿尔茨海默病；将其用作激酶抑制剂；含有同样化合物的药物组合物；以及制备同样化合物的方法。
• [EN] DERIVATIVES OF AZAINDAZOLE OR DIAZAINDAZOLE TYPE FOR TREATING PAIN<br/>[FR] DÉRIVÉS DE TYPE AZA-INDAZOLE OU DIAZA-INDAZOLE POUR LE TRAITEMENT DE LA DOULEUR
  申请人：PF MEDICAMENT

  公开号：WO2014016433A1

  公开（公告）日：2014-01-30

  The present invention relates to a compound of following formula (I): or a pharmaceutically acceptable salt or solvate of same, a tautomer of same, or a stereoisomer or mixture of stereoisomers of same in any proportions, such as a mixture of enantiomers, notably a racemic mixture; for use in the treatment of pain.

  本发明涉及如下式(I)的化合物：或其药用可接受的盐或溶剂化物，其构象异构体，或其立体异构体或立体异构体混合物，以任何比例，例如对映体混合物，尤其是外消旋混合物；用于治疗疼痛。
• [EN] DERIVATIVES OF AZAINDAZOLE OR DIAZAINDAZOLE TYPE FOR TREATING A CANCER OVEREXPRESSING TRK<br/>[FR] DÉRIVÉS DE TYPE AZA-INDAZOLE OU DIAZA-INDAZOLE POUR LE TRAITEMENT D'UN CANCER SUREXPRIMANT LA TRK
  申请人：PF MEDICAMENT

  公开号：WO2014016434A1

  公开（公告）日：2014-01-30

  The present invention relates to a compound of following formula (I) or a pharmaceutically acceptable salt or solvate of same, a tautomer of same, or a stereoisomer or mixture of stereoisomers of same in any proportions, such as a mixture of enantiomers, notably a racemic mixture, as well as pharmaceutical composition comprising such a compound, for use in the treatment of a cancer associated with the overexpression of at least one Trk protein.

  本发明涉及式(I)所示的化合物，或其药用可接受的盐或溶剂化物，其同分异构体，或其立体异构体或立体异构体混合物，以任何比例，例如对映体混合物，尤其是外消旋混合物，以及包含该化合物的药物组合物，用于治疗与至少一种Trk蛋白过表达相关的癌症。
• Derivatives of azaindazole or diazaindazole type for treating a cancer overexpressing trk
  申请人：PIERRE FABRE MEDICAMENT

  公开号：EP2689779A1

  公开（公告）日：2014-01-29

  The present invention relates to a compound of following formula (I): or a pharmaceutically acceptable salt or solvate of same, a tautomer of same, or a stereoisomer or mixture of stereoisomers of same in any proportions, such as a mixture of enantiomers, notably a racemic mixture, as well as pharmaceutical composition comprising such a compound, for use in the treatment of a cancer associated with the overexpression of at least one Trk protein.

  本发明涉及具有以下公式(I)的化合物： 或其药用可接受的盐或溶剂化物，其互变异构体，或其立体异构体或立体异构体混合物，以任何比例，如对映体混合物，尤其是外消旋混合物，以及包含该化合物的药物组合物，用于治疗与至少一种Trk蛋白过度表达相关的癌症。
• [EN] DERIVATIVES OF AZAINDAZOLE OR DIAZAINDAZOLE TYPE AS MEDICAMENT<br/>[FR] DÉRIVÉS DE TYPE AZAINDAZOLE OU DIAZAINDAZOLE UTILISÉS COMME MÉDICAMENTS
  申请人：PF MEDICAMENT

  公开号：WO2012101239A1

  公开（公告）日：2012-08-02

  The present invention relates to a compound of following formula (I): or a pharmaceutically acceptable salt or solvate of same, a tautomer of same, or a stereoisomer or mixture of stereoisomers of same in any proportions, such as a mixture of enantiomers, notably a racemic mixture; as well as to the use of same as a drug, notably intended for the treatment of cancer, inflammation and neurodegenerative diseases such as Alzheimer's disease; to the use of same as a kinase inhibitor; to the pharmaceutical compositions comprising same; and to methods for the preparation of same.

  本发明涉及式(I)所示的化合物：或其药用可接受的盐或溶剂化物，其构象异构体，或其立体异构体或立体异构体混合物，以任何比例，例如对映异构体的混合物，尤其是外消旋混合物；以及将上述化合物作为药物的使用，尤其是用于治疗癌症、炎症和神经退行性疾病如阿尔茨海默病；作为激酶抑制剂的使用；包含它们的药物组合物；以及制造它们的方法。

表征谱图