Tert-butyl 4-(3,4-dichlorophenyl)-6,6-difluoro-3-oxo-1,4-diazepane-1-carboxylate | 1188535-27-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Tert-butyl 4-(3,4-dichlorophenyl)-6,6-difluoro-3-oxo-1,4-diazepane-1-carboxylate
• 英文别名: tert-butyl 4-(3,4-dichlorophenyl)-6,6-difluoro-3-oxo-1,4-diazepane-1-carboxylate
• CAS: 1188535-27-4
• 化学式: C₁₆H₁₈Cl₂F₂N₂O₃
• 分子量: 395.233
• InChiKey: CEVSLWDRYXPKKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Tert-butyl 4-(3,4-dichlorophenyl)-6,6-difluoro-3-oxo-1,4-diazepane-1-carboxylate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 以75%的产率得到1-(3,4-Dichlorophenyl)-6,6-difluoro-1,4-diazepan-2-one;hydrochloride
  参考文献：
  名称：

  Design, synthesis, and biological activities of 1-aryl-1,4-diazepan-2-one derivatives as novel triple reuptake inhibitors

  摘要：

  A novel series of triple reuptake inhibitors were explored by ligand-based drug design. A cyclic structure was designed from cyclopropane derivative 5 using the core structure of reported monoamine reuptake inhibitors, leading to the formation of the 1-aryl-1,4-diazepan-2-one derivative 23j-S. Compound 23j-S was shown to act as a potent TRI with an excellent ADME-Tox profile. Oral administration of 23j-S significantly enhanced norepinephrine, dopamine, and serotonin levels in the mouse prefrontal cortex and showed significant antidepressant-like activity in tail suspension tests in mouse.

  DOI：

  10.1016/j.bmcl.2014.06.046
• 作为产物：
  描述：

  3,4-二氯碘苯 在 potassium phosphate 、 1-羟基-1H-苯并三唑铵盐 、 硼烷四氢呋喃络合物 、 sodium hydride 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 copper(I) bromide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 Tert-butyl 4-(3,4-dichlorophenyl)-6,6-difluoro-3-oxo-1,4-diazepane-1-carboxylate
  参考文献：
  名称：

  Design, synthesis, and biological activities of 1-aryl-1,4-diazepan-2-one derivatives as novel triple reuptake inhibitors

  摘要：

  A novel series of triple reuptake inhibitors were explored by ligand-based drug design. A cyclic structure was designed from cyclopropane derivative 5 using the core structure of reported monoamine reuptake inhibitors, leading to the formation of the 1-aryl-1,4-diazepan-2-one derivative 23j-S. Compound 23j-S was shown to act as a potent TRI with an excellent ADME-Tox profile. Oral administration of 23j-S significantly enhanced norepinephrine, dopamine, and serotonin levels in the mouse prefrontal cortex and showed significant antidepressant-like activity in tail suspension tests in mouse.

  DOI：

  10.1016/j.bmcl.2014.06.046

文献信息

• [EN] HETEROCYCLIC COMPOUND<br/>[FR] COMPOSÉ HÉTÉROCYCLIQUE
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2009119528A1

  公开（公告）日：2009-10-01

  　本発明は、モノアミン神経伝達物質取り込み阻害作用を有する化合物を提供する。本発明は、式（Ｉ）： 〔式中、各記号は明細書本文と同意義である。〕で表される化合物またはその塩に関する。
• Design, synthesis, and biological activities of 1-aryl-1,4-diazepan-2-one derivatives as novel triple reuptake inhibitors
  作者：Eiji Honda、Yuji Ishichi、Eiji Kimura、Masato Yoshikawa、Naoyuki Kanzaki、Hideyuki Nakagawa、Yasuko Terao、Atsuko Suzuki、Takayuki Kawai、Yuuichi Arakawa、Hiroyuki Ohta、Jun Terauchi

  DOI：10.1016/j.bmcl.2014.06.046

  日期：2014.8

  A novel series of triple reuptake inhibitors were explored by ligand-based drug design. A cyclic structure was designed from cyclopropane derivative 5 using the core structure of reported monoamine reuptake inhibitors, leading to the formation of the 1-aryl-1,4-diazepan-2-one derivative 23j-S. Compound 23j-S was shown to act as a potent TRI with an excellent ADME-Tox profile. Oral administration of 23j-S significantly enhanced norepinephrine, dopamine, and serotonin levels in the mouse prefrontal cortex and showed significant antidepressant-like activity in tail suspension tests in mouse.