N^α-Boc-Ala-N^α-benzylglycine ethyl ester | 86666-85-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: N^α-Boc-Ala-N^α-benzylglycine ethyl ester
• 英文别名: ethyl N'-(tert-butoxycarbonyl)-L-alanyl-N-benzylglycinate；(S)-Ethyl 2-(N-benzyl-2-(tert-butoxycarbonylamino)-propanamido)acetate；ethyl 2-[benzyl-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]acetate
• CAS: 86666-85-5
• 化学式: C₁₉H₂₈N₂O₅
• 分子量: 364.442
• InChiKey: QDVGBJVGISYIDQ-AWEZNQCLSA-N

物化性质

• 沸点：
  508.5±45.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N^α-Boc-Ala-N^α-benzylglycine ethyl ester 反应 0.05h， 以84%的产率得到2,5-哌嗪二酮,3-甲基-1-(苯基甲基)-,(3S)-
  参考文献：
  名称：

  无溶剂条件下 2,5-哌嗪二酮的微波辅助合成

  摘要：

  描述了一种合成 2,5-哌嗪二酮的通用、高效和环保的方法，包括 N-Boc 二肽酯的微波辐射。

  DOI：

  10.1055/s-2005-918473
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丙氨酸 、 N-苄基甘氨酸乙酯 在 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， 反应 24.0h， 以0.54 g的产率得到N^α-Boc-Ala-N^α-benzylglycine ethyl ester
  参考文献：
  名称：

  无溶剂条件下 2,5-哌嗪二酮的微波辅助合成

  摘要：

  描述了一种合成 2,5-哌嗪二酮的通用、高效和环保的方法，包括 N-Boc 二肽酯的微波辐射。

  DOI：

  10.1055/s-2005-918473

文献信息

• Design and Synthesis of Novel Conformationally Restricted Peptide Secondary Structure Mimetics
  作者：Hwa-Ok Kim、Hiroshi Nakanishi、Min S. Lee、Michael Kahn

  DOI：10.1021/ol990355r

  日期：2000.2.1

  [structure: see text] A facile synthesis of the novel conformationally restricted reverse turn mimetic is described. The key features are the preparation of the alpha-keto amide and tandem bicyclic ring formation.

  [结构：见正文]描述了新型构象受限的反向转弯模拟物的简便合成。主要特征是制备α-酮酰胺和串联双环。
• Exploring the Structure−Activity Relationships of [1-(4-<i>tert</i>-Butyl-3‘-hydroxy)benzhydryl-4-benzylpiperazine] (SL-3111), A High-Affinity and Selective δ-Opioid Receptor Nonpeptide Agonist Ligand
  作者：Josue Alfaro-Lopez、Toru Okayama、Keiko Hosohata、Peg Davis、Frank Porreca、Henry I. Yamamura、Victor J. Hruby

  DOI：10.1021/jm990337f

  日期：1999.12.1

  SL-3111 [1-(4-tert-butyl-3'-hydroxy)benzhydryl-4-benzylpiperazine] is a de novo designed, high-affinity and selective nonpeptide peptidomimetic agonist of the delta-opioid receptor. In a previous report we had described the unique biological characteristics of this ligand and also a need for further structural evaluation(6). To pursue this, we have introduced a completely different heterocyclic template (2 and 3), which, based on molecular modeling studies, may present the required structural features to properly orient the pharmacophore groups. We also have made more subtle changes to the original piperazine scaffold (5 and 11). The biological activities of these compounds revealed an important participation of the scaffold in the ligand-receptor interaction. To further explore functional diversity on the scaffold, we have maintained the original piperazine ring and introduced four different functionalities at position 2 of the heterocyclic ring (15a-d; a = CH2-O-CH2-Ph; b = Me; c = CH2Ph; d = CH2OH). The biological activities observed for these compounds showed a very interesting trend in terms of the steric effects of the groups introduced at this position. A decrease of almost 2000-fold in affinity and potency at the delta-receptor was observed for 15c compared with 15b. This difference may be explained if we postulate that the bioactive conformation of these peptidomimetics is close to the minimal energy conformations calculated in our study. On the basis of these findings we have realized the importance of this position to further explore and simplify the structure of future generations of peptidomimetic ligands.
• US7598253B2
  申请人：——

  公开号：US7598253B2

  公开（公告）日：2009-10-06