2-(4-(3-(2-chloro-10H-phenothiazin-10-yl)propyl)piperazin-1-yl)ethyl 4-((tert-butoxycarbonyl)amino)butanoate-4-14C | 1021521-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-(4-(3-(2-chloro-10H-phenothiazin-10-yl)propyl)piperazin-1-yl)ethyl 4-((tert-butoxycarbonyl)amino)butanoate-4-14C
• CAS: 1021521-09-4
• 化学式: C₃₀H₄₁ClN₄O₄S
• 分子量: 591.188
• InChiKey: FRMWLKOZSLBKLP-ALWQSETLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  74.35
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(4-(3-(2-chloro-10H-phenothiazin-10-yl)propyl)piperazin-1-yl)ethyl 4-((tert-butoxycarbonyl)amino)butanoate-4-14C 、 顺丁烯二酸 在 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 [14C]-4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-1-piperazineethyl aminobutyryl ester trimaleate
  参考文献：
  名称：

  A Mutual Prodrug Ester of GABA and Perphenazine Exhibits Antischizophrenic Efficacy with Diminished Extrapyramidal Effects

  摘要：

  The perphenazine and fluphenazine GABA esters 3 and 4 evaluated in rat models for antipsychotic activity displayed a significant decrease of catalepsy associated with increased prolactin blood levels. Efficacy was evaluated in the D-amphetamine-induced hyperactivity model, where perphenazine abolished hyperactivity and induced sedation and catalepsy, whereas 3 reduced hyperactivity without sedation or catalepsy. Thus, 3 (BL-1020) constitutes a prototype of novel antipsychotics possessing GABAergic activity. A phase II study is in progress.

  DOI：

  10.1021/jm7012453
• 作为产物：
  描述：

  [14C]-4-N-tert-butoxycarbonylaminobutyric acid 、 奋乃静 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 2-(4-(3-(2-chloro-10H-phenothiazin-10-yl)propyl)piperazin-1-yl)ethyl 4-((tert-butoxycarbonyl)amino)butanoate-4-14C
  参考文献：
  名称：

  A Mutual Prodrug Ester of GABA and Perphenazine Exhibits Antischizophrenic Efficacy with Diminished Extrapyramidal Effects

  摘要：

  The perphenazine and fluphenazine GABA esters 3 and 4 evaluated in rat models for antipsychotic activity displayed a significant decrease of catalepsy associated with increased prolactin blood levels. Efficacy was evaluated in the D-amphetamine-induced hyperactivity model, where perphenazine abolished hyperactivity and induced sedation and catalepsy, whereas 3 reduced hyperactivity without sedation or catalepsy. Thus, 3 (BL-1020) constitutes a prototype of novel antipsychotics possessing GABAergic activity. A phase II study is in progress.

  DOI：

  10.1021/jm7012453