3(R)-[(4(S)-((4-azidobenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide | 874163-06-1

• 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: 3(R)-[(4(S)-((4-azidobenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide
• 英文别名: tert-butyl (2S,4S)-2-[[(3R)-1-(2-amino-2-oxoethyl)-2-oxopyrrolidin-3-yl]carbamoyl]-4-[(4-azidobenzoyl)amino]pyrrolidine-1-carboxylate
• CAS: 874163-06-1
• 化学式: C₂₃H₃₀N₈O₆
• 分子量: 514.541
• InChiKey: CCXXAJSAGGRHFC-BBWFWOEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  166
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3(R)-[(4(S)-((4-azidobenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以86%的产率得到3(R)-[(4(S)-(4-azidobenzoyl)amino-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide hydrochloride
  参考文献：
  名称：

  Design and Synthesis of Photoaffinity-Labeling Ligands of the l-Prolyl-l-leucylglycinamide Binding Site Involved in the Allosteric Modulation of the Dopamine Receptor

  摘要：

  Pro-Leu-Gly-NH2 (PLG), in addition to its endocrine effects, possesses the ability to modulate dopamine D-2 receptors within the central nervous system. However, the precise binding site of PLG is unknown. Potential photoaffinity-labeling ligands of the PLG binding site were designed as tools to be used in the identification of the macromolecule that possesses this binding site. Six different photoaffinity-labeling ligands were designed and synthesized on the basis of the gamma-lactam PLG peptidomimetic 1. The 4-azidobenzoyl and 4-azido-2-hydroxybenzoyl photoaffinity-labeling moieties were placed at opposite ends of PLG peptidomimetic I to generate a series of ligands that potentially could be used to map the PLG binding site. All of the compounds that were synthesized possessed activity comparable to or better than PLG in enhancing [H-3]-N-propylnorapomorphine agonist binding to dopamine receptors. Photoaffinity ligands that were crosslinked to the receptor preparation produced a modulatory effect that was either comparable to or greater than the increase in agonist binding produced by the respective ligands that were not cross-linked to the dopamine receptor. The results indicate that these photoaffinity-labeling agents are binding at the same allosteric site as PLG and PLG peptidomimetic 1.

  DOI：

  10.1021/jm050644n
• 作为产物：
  描述：

  2-benzyl 1-(tert-butyl) (2S,4R)-4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate 在 palladium on activated charcoal N-甲基哌啶 、 sodium hydroxide 、 sodium azide 、 2-氯-1-甲基吡啶碘化物 、 氨 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 55.0 ℃ 、517.11 kPa 条件下， 反应 168.5h， 生成 3(R)-[(4(S)-((4-azidobenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide
  参考文献：
  名称：

  Design and Synthesis of Photoaffinity-Labeling Ligands of the l-Prolyl-l-leucylglycinamide Binding Site Involved in the Allosteric Modulation of the Dopamine Receptor

  摘要：

  Pro-Leu-Gly-NH2 (PLG), in addition to its endocrine effects, possesses the ability to modulate dopamine D-2 receptors within the central nervous system. However, the precise binding site of PLG is unknown. Potential photoaffinity-labeling ligands of the PLG binding site were designed as tools to be used in the identification of the macromolecule that possesses this binding site. Six different photoaffinity-labeling ligands were designed and synthesized on the basis of the gamma-lactam PLG peptidomimetic 1. The 4-azidobenzoyl and 4-azido-2-hydroxybenzoyl photoaffinity-labeling moieties were placed at opposite ends of PLG peptidomimetic I to generate a series of ligands that potentially could be used to map the PLG binding site. All of the compounds that were synthesized possessed activity comparable to or better than PLG in enhancing [H-3]-N-propylnorapomorphine agonist binding to dopamine receptors. Photoaffinity ligands that were crosslinked to the receptor preparation produced a modulatory effect that was either comparable to or greater than the increase in agonist binding produced by the respective ligands that were not cross-linked to the dopamine receptor. The results indicate that these photoaffinity-labeling agents are binding at the same allosteric site as PLG and PLG peptidomimetic 1.

  DOI：

  10.1021/jm050644n

文献信息

• Design and Synthesis of Photoaffinity-Labeling Ligands of the <scp>l</scp>-Prolyl-<scp>l</scp>-leucylglycinamide Binding Site Involved in the Allosteric Modulation of the Dopamine Receptor
  作者：Abigail Fisher、Amandeep Mann、Vaneeta Verma、Nancy Thomas、Ram K. Mishra、Rodney L. Johnson

  DOI：10.1021/jm050644n

  日期：2006.1.1

  Pro-Leu-Gly-NH2 (PLG), in addition to its endocrine effects, possesses the ability to modulate dopamine D-2 receptors within the central nervous system. However, the precise binding site of PLG is unknown. Potential photoaffinity-labeling ligands of the PLG binding site were designed as tools to be used in the identification of the macromolecule that possesses this binding site. Six different photoaffinity-labeling ligands were designed and synthesized on the basis of the gamma-lactam PLG peptidomimetic 1. The 4-azidobenzoyl and 4-azido-2-hydroxybenzoyl photoaffinity-labeling moieties were placed at opposite ends of PLG peptidomimetic I to generate a series of ligands that potentially could be used to map the PLG binding site. All of the compounds that were synthesized possessed activity comparable to or better than PLG in enhancing [H-3]-N-propylnorapomorphine agonist binding to dopamine receptors. Photoaffinity ligands that were crosslinked to the receptor preparation produced a modulatory effect that was either comparable to or greater than the increase in agonist binding produced by the respective ligands that were not cross-linked to the dopamine receptor. The results indicate that these photoaffinity-labeling agents are binding at the same allosteric site as PLG and PLG peptidomimetic 1.