2-((bis(4-chlorophenyl)methyl)thio)ethan-1-amine hydrochloride | 145701-76-4

• 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-((bis(4-chlorophenyl)methyl)thio)ethan-1-amine hydrochloride
• 英文别名: 2-[bis(4-chlorophenyl)methylsulfanyl]ethanamine;hydrochloride
• CAS: 145701-76-4
• 化学式: C₁₅H₁₅Cl₂NS*ClH
• 分子量: 348.724
• InChiKey: BEOQDJCFQDHUNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  26.02
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-((bis(4-chlorophenyl)methyl)thio)ethan-1-amine hydrochloride 、 肉桂醛 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 为溶剂， 生成 VUF8967
  参考文献：
  名称：

  New prenylamine analogues: synthesis and Ca2+-entry blocking activity

  摘要：

  The synthesis of a series of diphenylalkylamine derivatives related to prenylamine is reported. The amphetamine group in the prenylamine structure was replaced by other moieties. In addition to substitutions in the aromatic rings, heteroatoms such as sulphur and oxygen were introduced in the chain. The calcium-entry blocking activity was assayed in binding experiments on a guinea-pig brain membrane preparation by displacing [H-3]-nitrendipine.

  DOI：

  10.1016/0223-5234(92)90136-o
• 作为产物：
  描述：

  4,4'-二氯二苯甲醇 、 半胱胺盐酸盐 在 三氟化硼乙醚 、 溶剂黄146 作用下， 反应 0.83h， 以62%的产率得到2-((bis(4-chlorophenyl)methyl)thio)ethan-1-amine hydrochloride
  参考文献：
  名称：

  Elucidation of Structural Elements for Selectivity across Monoamine Transporters: Novel 2-[(Diphenylmethyl)sulfinyl]acetamide (Modafinil) Analogues

  摘要：

  2-[(Diphenylmethyl)sulfinyl]acetamide (modafinil, (+/-)-1) is a unique dopamine uptake inhibitor that binds the dopamine transporter (DAT) differently than cocaine and may have potential for the treatment of psychostimulant abuse. To further investigate structural requirements for this divergent binding mode, novel thio- and sulfinylacetamide and ethanamine analogues of (+/-)-1 were synthesized wherein (1) the diphenyl rings were substituted with methyl, trifluoromethyl, and halogen substituents and (2) substituents were added to the terminal amide/amine nitrogen. Halogen substitution of the diphenyl rings of (+/-)-1 gave several amide analogues with improved binding affinity for DAT and robust selectivity over the serotonin transporter (SERT), whereas affinity improved at SERT over DAT for the p-halo-substituted amine analogues. Molecular docking studies, using a subset of analogues with DAT and SEAT homology models, and functional data obtained with DAT (A480T) and SERT (T497A) mutants defined a role for TM10 in the substrate/inhibitor S1 binding sites of DAT and SERT.

  DOI：

  10.1021/jm401754x

文献信息

• [EN] POTENT AND SELECTIVE INHIBITORS OF MONOAMINE TRANSPORTERS; METHOD OF MAKING; AND USE THEREOF<br/>[FR] INHIBITEURS PUISSANTS ET SÉLECTIFS DE TRANSPORTEURS DE MONOAMINE; PROCÉDÉ DE FABRICATION; ET LEUR UTILISATION
  申请人：US HEALTH

  公开号：WO2014138518A3

  公开（公告）日：2014-11-06