benzyl N-[2-oxo-1-(2-oxoethyl)-5-phenyl-3H-1,4-benzodiazepin-3-yl]carbamate | 1345046-37-8

• 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: benzyl N-[2-oxo-1-(2-oxoethyl)-5-phenyl-3H-1,4-benzodiazepin-3-yl]carbamate
• CAS: 1345046-37-8
• 化学式: C₂₅H₂₁N₃O₄
• 分子量: 427.459
• InChiKey: IEKNTNOHINPGHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  88.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl N-[2-oxo-1-(2-oxoethyl)-5-phenyl-3H-1,4-benzodiazepin-3-yl]carbamate 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 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， 20.0 ℃ 、101.33 kPa 条件下， 生成 N-[2-oxo-1-(2-oxoethyl)-5-phenyl-3H-1,4-benzodiazepin-3-yl]-2-phenylacetamide
  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：

  benzyl N-[1-(2-hydroxyethyl)-2-oxo-5-phenyl-3H-1,4-benzodiazepin-3-yl]carbamate 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到benzyl N-[2-oxo-1-(2-oxoethyl)-5-phenyl-3H-1,4-benzodiazepin-3-yl]carbamate
  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