N-[(3,5-dichlorophenyl)methyl]cyclopropanamine | 1094641-89-0

• 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: N-[(3,5-dichlorophenyl)methyl]cyclopropanamine
• CAS: 1094641-89-0
• 化学式: C₁₀H₁₁Cl₂N
• mdl: MFCD11212569
• 分子量: 216.11
• InChiKey: XPLRLEHFWZCNLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-[(3,5-dichlorophenyl)methyl]cyclopropanamine 在 potassium carbonate 、 lithium hexamethyldisilazane 、 肼 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 5-((cyclopropyl(3,5-dichlorobenzyl)amino)methyl)-1H-pyrazol-3(2H)-one
  参考文献：
  名称：

  Tertiary Amine Pyrazolones and Their Salts as Inhibitors of Mutant Superoxide Dismutase 1-Dependent Protein Aggregation for the Treatment of Amyotrophic Lateral Sclerosis

  摘要：

  Pyrazolone derivatives have previously been found to be inhibitors of Cu/Zn superoxide dismutase 1 (S OD 1) - dep en dent protein aggregation, which extended survival of an amyotrophic lateral sclerosis (ALS) mouse model. On the basis of ADME analysis, we describe herein a new series of tertiary amine-containing pyrazolones and their structure activity relationships. Further conversion to the conjugate salts greatly improved their solubility. Phosphate compound 17 exhibited numerous benefits both to cellular activity and to CNS-related drug-like properties in vitro and in vivo, including microsomal stability, tolerated toxicity, and blood brain barrier permeation. These results indicate that tertiary amine pyrazolones comprise a valuable class of ALS drug candidates.

  DOI：

  10.1021/acs.jmedchem.5b00561
• 作为产物：
  描述：

  3,5-二氯苯甲醛 、 环丙胺 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 N-[(3,5-dichlorophenyl)methyl]cyclopropanamine
  参考文献：
  名称：

  Tertiary Amine Pyrazolones and Their Salts as Inhibitors of Mutant Superoxide Dismutase 1-Dependent Protein Aggregation for the Treatment of Amyotrophic Lateral Sclerosis

  摘要：

  Pyrazolone derivatives have previously been found to be inhibitors of Cu/Zn superoxide dismutase 1 (S OD 1) - dep en dent protein aggregation, which extended survival of an amyotrophic lateral sclerosis (ALS) mouse model. On the basis of ADME analysis, we describe herein a new series of tertiary amine-containing pyrazolones and their structure activity relationships. Further conversion to the conjugate salts greatly improved their solubility. Phosphate compound 17 exhibited numerous benefits both to cellular activity and to CNS-related drug-like properties in vitro and in vivo, including microsomal stability, tolerated toxicity, and blood brain barrier permeation. These results indicate that tertiary amine pyrazolones comprise a valuable class of ALS drug candidates.

  DOI：

  10.1021/acs.jmedchem.5b00561