tert-butyl (3S)-3-[(9H)-(9-fluorenyl)methoxycarbonyl]amino-4-oxo-9-phenylnonanoate | 273216-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: tert-butyl (3S)-3-[(9H)-(9-fluorenyl)methoxycarbonyl]amino-4-oxo-9-phenylnonanoate
• 英文别名: tert-butyl (3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-9-phenylnonanoate
• CAS: 273216-16-3
• 化学式: C₃₄H₃₉NO₅
• 分子量: 541.687
• InChiKey: OKKQBMGWRBSVNK-PMERELPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-溴烟酸 、 tert-butyl (3S)-3-[(9H)-(9-fluorenyl)methoxycarbonyl]amino-4-oxo-9-phenylnonanoate 生成 (S)-3-[(5-Bromo-pyridine-3-carbonyl)-amino]-4-oxo-9-phenyl-nonanoic acid
  参考文献：
  名称：

  Nicotinyl aspartyl ketones as inhibitors of caspase-3

  摘要：

  Caspase-3 is a cysteinyl protease that mediates apoptotic cell death. Its inhibition may have an important impact in the treatment of several degenerative diseases. Since P, aspartic acid is a required element of recognition for this enzyme, a library of capped aspartyl aldehydes was synthesized using solid-phase chemistry. The 5-bromonicotinamide derivative of the aspartic acid aldehyde was identified to be an inhibitor of caspase-3. Substitution at the 5-position of the pyridine ring and conversion of the aldehyde to ketones led to a series of potent inhibitors of caspase-3. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00390-1
• 作为产物：
  描述：

  N-(fluorenylmethyloxycarbonyl)-L-aspart-α-al β-tert-butyl ester 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyl (3S)-3-[(9H)-(9-fluorenyl)methoxycarbonyl]amino-4-oxo-9-phenylnonanoate
  参考文献：
  名称：

  Nicotinyl aspartyl ketones as inhibitors of caspase-3

  摘要：

  Caspase-3 is a cysteinyl protease that mediates apoptotic cell death. Its inhibition may have an important impact in the treatment of several degenerative diseases. Since P, aspartic acid is a required element of recognition for this enzyme, a library of capped aspartyl aldehydes was synthesized using solid-phase chemistry. The 5-bromonicotinamide derivative of the aspartic acid aldehyde was identified to be an inhibitor of caspase-3. Substitution at the 5-position of the pyridine ring and conversion of the aldehyde to ketones led to a series of potent inhibitors of caspase-3. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00390-1

文献信息

• Nicotinyl aspartyl ketones as inhibitors of caspase-3
  作者：Elise Isabel、W.Cameron Black、Christopher I Bayly、Erich L Grimm、Marc K Janes、Daniel J McKay、Donald W Nicholson、Dita M Rasper、Johanne Renaud、Sophie Roy、John Tam、Nancy A Thornberry、John P Vaillancourt、Steven Xanthoudakis、Robert Zamboni

  DOI：10.1016/s0960-894x(03)00390-1

  日期：2003.7

  Caspase-3 is a cysteinyl protease that mediates apoptotic cell death. Its inhibition may have an important impact in the treatment of several degenerative diseases. Since P, aspartic acid is a required element of recognition for this enzyme, a library of capped aspartyl aldehydes was synthesized using solid-phase chemistry. The 5-bromonicotinamide derivative of the aspartic acid aldehyde was identified to be an inhibitor of caspase-3. Substitution at the 5-position of the pyridine ring and conversion of the aldehyde to ketones led to a series of potent inhibitors of caspase-3. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Solid phase synthesis of selective caspase-3 peptide inhibitors
  作者：Erich L Grimm、Bruno Roy、Renee Aspiotis、Christopher I Bayly、Donald W Nicholson、Dita M Rasper、Johanne Renaud、Sophie Roy、John Tam、Paul Tawa、John P Vaillancourt、Steven Xanthoudakis、Robert J Zamboni

  DOI：10.1016/j.bmc.2004.01.007

  日期：2004.3

  A robust method for the solid phase synthesis of a series of selective caspase-3 peptide inhibitors is described. The inhibitors can be obtained after cleavage from the solid support without further purification. (C) 2004 Elsevier Ltd. All rights reserved.