(S)-7-chloro-1,3-dihydro-3-(1H-indol-3-ylmethyl)-5-phenyl-2H-1,4-benzodiazepin-2-one | 50691-94-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: (S)-7-chloro-1,3-dihydro-3-(1H-indol-3-ylmethyl)-5-phenyl-2H-1,4-benzodiazepin-2-one
• 英文别名: (S)-7-chloro-1,3-dihydro-3-(3'-indolyl)methyl-5-phenyl-2H-1,3-benzodiazepine-2-one；7-Chloro-1,3-dihydro-3(S)-(3'-indolyl)methyl-5-phenyl-2H-1,4-benzodiazepin-2-one；2H-1,4-Benzodiazepin-2-one, 1,3-dihydro-7-chloro-3-(1H-indol-3-ylmethyl)-5-phenyl-, (S)-；(3S)-7-chloro-3-(1H-indol-3-ylmethyl)-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
• CAS: 50691-94-6
• 化学式: C₂₄H₁₈ClN₃O
• 分子量: 399.879
• InChiKey: OAAIQFQHSUFGKD-QFIPXVFZSA-N

物化性质

• 沸点：
  640.8±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-7-chloro-1,3-dihydro-3-(1H-indol-3-ylmethyl)-5-phenyl-2H-1,4-benzodiazepin-2-one 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 反应 0.25h， 生成 7-Chloro-1,3,4,5-tetrahydro-3(S)-(3'-indolyl)methyl-5-phenyl-2H-1,4-benzodiazepin-2-one
  参考文献：
  名称：

  肽受体的非肽配体的设计：胆囊收缩素拮抗剂。

  摘要：

  已经合成了一系列3-取代的5-苯基-1,4-苯并二氮杂卓，它们是肽激素胆囊收缩素（CCK）的非肽拮抗剂。根据有关CCK，其天然产物拮抗剂Asperlicin（3）和抗焦虑药地西epa（4）的事实进行设计，这些化合物与现有的CCK拮抗剂有很大的不同。它们也可能构成通过设计而不是通过筛选产生的肽受体的简单，非肽配体的第一个实例。这些化合物用于阐明中枢和外周CCK受体之间的区别，并提供具有潜在药理或治疗用途的口服有效CCK拮抗剂。他们的受体亲和力的一个基本原理可能会在设计其他受体的非肽配体时应用，

  DOI：

  10.1021/jm00390a019
• 作为产物：
  描述：

  N-叔丁氧羰基-L-色氨酸 在 盐酸 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 18.0h， 生成 (S)-7-chloro-1,3-dihydro-3-(1H-indol-3-ylmethyl)-5-phenyl-2H-1,4-benzodiazepin-2-one
  参考文献：
  名称：

  Discrimination between Enantiomers of Structurally Related Molecules:  Separation of Benzodiazepines by Molecularly Imprinted Polymers

  摘要：

  Molecular imprinting has been used to create synthetic receptor sites for a series of chiral benzodiazepines. A detailed HPLC analysis of binding properties using molecularly imprinted polymers (MIPs) as the stationary phase showed that binding, as measured by chromatographic retention, shows significant dependence on the chiral match or mismatch. In addition, the shape and spatial orientation of functionality of the imprinted binding site is also critical for recognition. Imprinted polymers, therefore, are not only able to discriminate between enantiomers of the imprinted molecule, they also demonstrate an ability to discriminate between a wide range of enantiomers of structurally related molecules that have not been imprinted. The ability of MIPs to discriminate between enantiomers of molecules in favor of the imprinted absolute configuration, even as the structural homology between the enantiomers and the original template decreases, indicates that the synthetic benzodiazepine receptors may serve as crude mimics of the natural receptor.

  DOI：

  10.1021/ja9926313

文献信息

• Benzodiazepine analogs
  申请人：Merck & Co., Inc.

  公开号：US04820834A1

  公开（公告）日：1989-04-11

  Benzodiazepine analogs of the formula: ##STR1## are disclosed which are antagonists of gastrin and cholecystokinin (CCK).

  公开了一种化学式为##STR1##的苯二氮䓬类似物，它们是胃泌素和胆囊收缩素（CCK）的拮抗剂。
• Benzodiazepine derivatives and pharmaceutical compositions containing them
  申请人：Merck & Co., Inc.

  公开号：EP0167919A2

  公开（公告）日：1986-01-15

  Benzodiazepine analogs of the formula: are disclosed which are antagonists of cholecystokinin (CCK).

  式中的苯二氮卓类似物： 公开了胆囊收缩素（CCK）拮抗剂。
• US4820834A
  申请人：——

  公开号：US4820834A

  公开（公告）日：1989-04-11
• US5004741A
  申请人：——

  公开号：US5004741A

  公开（公告）日：1991-04-02
• Discrimination between Enantiomers of Structurally Related Molecules:  Separation of Benzodiazepines by Molecularly Imprinted Polymers
  作者：Bradley R. Hart、Daniel J. Rush、Kenneth J. Shea

  DOI：10.1021/ja9926313

  日期：2000.1.1

  Molecular imprinting has been used to create synthetic receptor sites for a series of chiral benzodiazepines. A detailed HPLC analysis of binding properties using molecularly imprinted polymers (MIPs) as the stationary phase showed that binding, as measured by chromatographic retention, shows significant dependence on the chiral match or mismatch. In addition, the shape and spatial orientation of functionality of the imprinted binding site is also critical for recognition. Imprinted polymers, therefore, are not only able to discriminate between enantiomers of the imprinted molecule, they also demonstrate an ability to discriminate between a wide range of enantiomers of structurally related molecules that have not been imprinted. The ability of MIPs to discriminate between enantiomers of molecules in favor of the imprinted absolute configuration, even as the structural homology between the enantiomers and the original template decreases, indicates that the synthetic benzodiazepine receptors may serve as crude mimics of the natural receptor.