3-[7-Chloro-5-(2-chloro-phenyl)-2-oxo-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-pyrrolidine-1-carboxylic acid benzyl ester | 93592-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-[7-Chloro-5-(2-chloro-phenyl)-2-oxo-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-pyrrolidine-1-carboxylic acid benzyl ester
• CAS: 93592-10-0
• 化学式: C₂₇H₂₃Cl₂N₃O₃
• 分子量: 508.404
• InChiKey: JOTYISQDVOXODJ-UHFFFAOYSA-N

物化性质

• 沸点：
  709.0±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

反应信息

• 作为反应物：
  描述：

  3-[7-Chloro-5-(2-chloro-phenyl)-2-oxo-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-pyrrolidine-1-carboxylic acid benzyl ester 在 三氯化铝 、 苯甲醚 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 7-Chloro-5-(2-chloro-phenyl)-1-pyrrolidin-3-yl-1,3-dihydro-benzo[e][1,4]diazepin-2-one
  参考文献：
  名称：

  1-Azacycloalkyl-1,4-benzodiazepin-2-ones with antianxiety-antidepressant actions

  摘要：

  A series of 1-azacycloalkyl-1,4-benzodiazepin-2-ones were synthesized from 1-azacycloalkyl-2-benzoylanilines and corresponding imines and then evaluated for their central nervous system activities. Pharmacological data showed that some of these compounds have potent antidepressant properties, as assessed by their antagonism of tetrabenzine (TBZ) induced ptosis and their inhibition of [3H]norepinephrine uptake into rat brain synaptosomes, as well as their moderate antianxiety properties of preventing of pentylenetetrazol (PTZ) convulsion, suppressing conflict behavior, and displacing potential for [3H]diazepam binding. Introduction of a halogen substituent at position 7 of the 1,4-benzodiazepine ring lengthened the anti-PTZ effects, although the peak effect was slightly reduced and clearly enhanced the anti-PTZ and anticonflict properties. Introduction of Cl to the ortho position of the phenyl ring at position 5 greatly reduced the antidepressant properties. The secondary amine function of the azacyclic ring at position 1 was essential for the production of the antidepressant properties. Of these new series, 7-fluoro-5-(2-fluorophenyl)-1,3-dihydro-1-(4-piperidinyl)-2H-1,4-benzodi azepin-2 -one has the potential to become a useful antidepressant drug with a moderate antianxiety property.

  DOI：

  10.1021/jm00383a003
• 作为产物：
  描述：

  3-[[4-Chloro-2-(2-chloro-benzoyl)-phenyl]-(2-iodo-acetyl)-amino]-pyrrolidine-1-carboxylic acid benzyl ester; hydrochloride 在 碳酸氢铵 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 3-[7-Chloro-5-(2-chloro-phenyl)-2-oxo-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  1-Azacycloalkyl-1,4-benzodiazepin-2-ones with antianxiety-antidepressant actions

  摘要：

  A series of 1-azacycloalkyl-1,4-benzodiazepin-2-ones were synthesized from 1-azacycloalkyl-2-benzoylanilines and corresponding imines and then evaluated for their central nervous system activities. Pharmacological data showed that some of these compounds have potent antidepressant properties, as assessed by their antagonism of tetrabenzine (TBZ) induced ptosis and their inhibition of [3H]norepinephrine uptake into rat brain synaptosomes, as well as their moderate antianxiety properties of preventing of pentylenetetrazol (PTZ) convulsion, suppressing conflict behavior, and displacing potential for [3H]diazepam binding. Introduction of a halogen substituent at position 7 of the 1,4-benzodiazepine ring lengthened the anti-PTZ effects, although the peak effect was slightly reduced and clearly enhanced the anti-PTZ and anticonflict properties. Introduction of Cl to the ortho position of the phenyl ring at position 5 greatly reduced the antidepressant properties. The secondary amine function of the azacyclic ring at position 1 was essential for the production of the antidepressant properties. Of these new series, 7-fluoro-5-(2-fluorophenyl)-1,3-dihydro-1-(4-piperidinyl)-2H-1,4-benzodi azepin-2 -one has the potential to become a useful antidepressant drug with a moderate antianxiety property.

  DOI：

  10.1021/jm00383a003