2-(3-amino-2-oxo-5-phenyl-3H-1,4-benzodiazepin-1-yl)acetaldehyde | 1345046-39-0

• 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: 2-(3-amino-2-oxo-5-phenyl-3H-1,4-benzodiazepin-1-yl)acetaldehyde
• CAS: 1345046-39-0
• 化学式: C₁₇H₁₅N₃O₂
• 分子量: 293.325
• InChiKey: INCPUFXAWSKUGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  75.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-二氯苯甲酸 、 2-(3-amino-2-oxo-5-phenyl-3H-1,4-benzodiazepin-1-yl)acetaldehyde 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 2,4-dichloro-N-[2-oxo-1-(2-oxoethyl)-5-phenyl-3H-1,4-benzodiazepin-3-yl]benzamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of benzodiazepine-based SUMO-specific protease 1 inhibitors

  摘要：

  As the best-characterized ubiquitin-like protein (UBL), small ubiquitin-related modifier (SUMO) was found to conjugate with a number of proteins to regulate cellular functions including transcription, signal transduction, and cell cycle. While E1, E2 and E3 ligases are responsible for the forward SUMOylation reaction, SUMO-specific proteases (SENPs) reversibly remove SUMO from the SUMOylated proteins. Recently, SENP1 was found to be a potential therapeutic target for the treatment of prostate cancers, but the design and synthesis of its inhibitors have not been reported. We designed and synthesized a series of benzodiazepine-based SENP1 inhibitors, and they showed inhibitory activity as good as IC(50) = 9.2 mu M (compound 38). The structure-activity relationship was also discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.101
• 作为产物：
  描述：

  苄基(2-氧代-5-苯基-2,3-二氢-1H-苯并[E][1,4]二氮杂-3-基)氨基甲酸叔丁酯 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 2-(3-amino-2-oxo-5-phenyl-3H-1,4-benzodiazepin-1-yl)acetaldehyde
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of benzodiazepine-based SUMO-specific protease 1 inhibitors

  摘要：

  As the best-characterized ubiquitin-like protein (UBL), small ubiquitin-related modifier (SUMO) was found to conjugate with a number of proteins to regulate cellular functions including transcription, signal transduction, and cell cycle. While E1, E2 and E3 ligases are responsible for the forward SUMOylation reaction, SUMO-specific proteases (SENPs) reversibly remove SUMO from the SUMOylated proteins. Recently, SENP1 was found to be a potential therapeutic target for the treatment of prostate cancers, but the design and synthesis of its inhibitors have not been reported. We designed and synthesized a series of benzodiazepine-based SENP1 inhibitors, and they showed inhibitory activity as good as IC(50) = 9.2 mu M (compound 38). The structure-activity relationship was also discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.101