cyclo-(-Azaphenylalanyl-L-prolyl-) | 148762-54-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cyclo-(-Azaphenylalanyl-L-prolyl-)
• 英文别名: cyclo(-azaPhe-Pro-)；c-[aza-phenylalaninyl-prolyl]；(8aS)-3-benzyl-6,7,8,8a-tetrahydro-2H-pyrrolo[1,2-d][1,2,4]triazine-1,4-dione
• CAS: 148762-54-3
• 化学式: C₁₃H₁₅N₃O₂
• 分子量: 245.281
• InChiKey: XFQRZMGCAKEALC-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cyclo-(-Azaphenylalanyl-L-prolyl-) 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 25.0~90.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 (1S,2S,4S)-7-benzyl-2-hydroxy-4-methyl-3-oxa-6,7,9-triazatricyclo[7.3.0.02,6]dodecane-5,8-dione
  参考文献：
  名称：

  Pinnen, Francesco; Luisi, Grazia; Lucente, Gino, Journal of the Chemical Society. Perkin transactions I, 1993, # 7, p. 819 - 824

  摘要：

  DOI：
• 作为产物：
  描述：

  N-tert-Butoxycarbonylazaphenylalanyl-L-proline 在 盐酸 、 乙酸乙酯 作用下， 反应 2.0h， 以72%的产率得到cyclo-(-Azaphenylalanyl-L-prolyl-)
  参考文献：
  名称：

  Pinnen, Francesco; Luisi, Grazia; Lucente, Gino, Journal of the Chemical Society. Perkin transactions I, 1993, # 7, p. 819 - 824

  摘要：

  DOI：

文献信息

• Solution-phase submonomer diversification of aza-dipeptide building blocks and their application in aza-peptide and aza-DKP synthesis
  作者：Carine B. Bourguet、Caroline Proulx、Sophie Klocek、David Sabatino、William D. Lubell

  DOI：10.1002/psc.1235

  日期：2010.6

  Aza‐peptides have been used as tools for studying SARs in programs aimed at drug discovery and chemical biology. Protected aza‐dipeptides were synthesized by a solution‐phase submonomer approach featuring alkylation of N‐terminal benzophenone semicarbazone aza‐Gly‐Xaa dipeptides using different alkyl halides in the presence of potassium tert‐butoxide as base. Benzophenone protected aza‐dipeptide tert‐butyl

  在针对药物发现和化学生物学的计划中，氮杂肽已用作研究SAR的工具。受保护的氮杂二肽是通过溶液相亚单体方法合成的，该方法以叔丁醇钾为碱，使用不同的烷基卤化物对N末端二苯甲酮半脲酮氮杂Gly-Xaa二肽进行烷基化。苯甲酮保护的氮杂二肽叔丁酯31c在C端酯或N处选择性脱保护末端分别提供氮杂二肽酸和胺结构单元36c和40c，它们被引入到更长的氮杂肽中。另外，从氮杂-二肽甲酯29a-c中去除二苯甲酮半脲酮保护导致分子内环化生成aza-DKPs 39a-c。鉴于氮杂肽和DKP作为治疗剂和生物过程探针的重要性，这种面向多样性的解决方案阶段方法可能为研究肽科学提供有用的工具。版权所有©2010欧洲肽协会和John Wiley＆Sons，Ltd.。
• Calcagni, Anna; Lucente, Gino; Luisi, Grazia, Journal of the Chemical Society. Perkin transactions I, 1997, # 15, p. 2223 - 2227
  作者：Calcagni, Anna、Lucente, Gino、Luisi, Grazia、Pinnen, Francesco、Rossi, Domenico、Gavuzzo, Enrico

  DOI：——

  日期：——
• Combinatorial Aid for Underprivileged Scaffolds: Solution and Solid-phase Strategies for a Rapid and Efficient Access To Novel Aza-diketopiperazines (Aza-DKP)
  作者：Dominique Bonnet、Jean-François Margathe、Sally Radford、Elsa Pflimlin、Stéphanie Riché、Pete Doman、Marcel Hibert、A. Ganesan

  DOI：10.1021/co300015k

  日期：2012.5.14

  An efficient solution-phase synthesis of aza-diketopiperazines (aza-DKP, triazinediones) is reported. A structurally diverse collection of c-[aza-alkylGly-Pro] derivatives and yet unreported 2,4,5-trisubstituted-1,2,4-triazine-3,6-diones has been synthesized starting from Fmoc-L-Pro-OH and various Fmoc-L-amino acids. To extend the practical value of this class of dipeptidomimetics, a general solid-phase synthesis approach amenable to library production was developed on both Wang-PS and HMBA-PS resins. The final acidic treatment of the resins in TFA/water mixture at room temperature enabled the rapid and quantitative cyclization/release highly pure triazinediones. The conformational preferences and the spatial organization of the three substituents of a representative 2,4,5-trisubstituted-1,2,4-triazine-3,6-dione were investigated by X-ray diffraction and H-1 NMR spectroscopy.
• Pinnen, Francesco; Luisi, Grazia; Lucente, Gino, Journal of the Chemical Society. Perkin transactions I, 1993, # 7, p. 819 - 824
  作者：Pinnen, Francesco、Luisi, Grazia、Lucente, Gino、Gavuzzo, Enrico、Cerrini, Silvio

  DOI：——

  日期：——