N-Fmoc-(2S)-alanyl-aza-phenylalanyl-(2S)-prolyl-diphenylmethyl amide | 1619943-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: N-Fmoc-(2S)-alanyl-aza-phenylalanyl-(2S)-prolyl-diphenylmethyl amide
• CAS: 1619943-49-5
• 化学式: C₄₄H₄₃N₅O₅
• 分子量: 721.856
• InChiKey: XQLFTHVGSARSQN-KBBVOBCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.94
• 重原子数：
  54.0
• 可旋转键数：
  10.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  120.08
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-Fmoc-(2S)-alanyl-aza-phenylalanyl-(2S)-prolyl-diphenylmethyl amide 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以65%的产率得到(2S)-alanyl-aza-phenylalanyl-(2S)-prolyl-diphenylmethyl amide
  参考文献：
  名称：

  Design and synthesis of novel azapeptide activators of apoptosis mediated by caspase-9 in cancer cells

  摘要：

  A set of azapeptides was designed based on the Ala-Val-Pro-Ile peptide (derived from Smac protein) to activate caspase-9 and induce apoptosis in breast cancer cells. The diversity-oriented synthesis of the aza-peptides 5-9 was accomplished by alkylation of the aza-residue of aza-Gly-Pro dipeptide 15 using potassium tert-butoxide and a range of different alkyl halides. The resulting protected aza-dipeptide building blocks were then introduced into mimics 5-9 using standard coupling conditions. Biological evaluation of 5-9 was performed in MDA-MB-231 breast cancer cells, and indicated that the aza-Gly and aza-Phe analogs 5 and 7 were most efficient in inducing cell death by a caspase-9 mediated apoptotic pathway. Revealing a relationship between azabicycloalkanone and aza peptide mimics, novel AVPI mimics were synthesized which exhibit utility for studying structure-activity relationships to develop leads for activating apoptosis in cancer cells. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.095
• 作为产物：
  描述：

  benzhydrylidene aza-phenylalaninyl-proline tert-butyl ester 在 N-甲基吗啉 、 吡啶 、 盐酸羟胺 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 15.0h， 生成 N-Fmoc-(2S)-alanyl-aza-phenylalanyl-(2S)-prolyl-diphenylmethyl amide
  参考文献：
  名称：

  Design and synthesis of novel azapeptide activators of apoptosis mediated by caspase-9 in cancer cells

  摘要：

  A set of azapeptides was designed based on the Ala-Val-Pro-Ile peptide (derived from Smac protein) to activate caspase-9 and induce apoptosis in breast cancer cells. The diversity-oriented synthesis of the aza-peptides 5-9 was accomplished by alkylation of the aza-residue of aza-Gly-Pro dipeptide 15 using potassium tert-butoxide and a range of different alkyl halides. The resulting protected aza-dipeptide building blocks were then introduced into mimics 5-9 using standard coupling conditions. Biological evaluation of 5-9 was performed in MDA-MB-231 breast cancer cells, and indicated that the aza-Gly and aza-Phe analogs 5 and 7 were most efficient in inducing cell death by a caspase-9 mediated apoptotic pathway. Revealing a relationship between azabicycloalkanone and aza peptide mimics, novel AVPI mimics were synthesized which exhibit utility for studying structure-activity relationships to develop leads for activating apoptosis in cancer cells. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.095