methyl 3(R)-[[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]carbonyl]amino]-3-benzyl-2-oxo-1-pyrrolidineacetate | 501380-91-2

• 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: methyl 3(R)-[[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]carbonyl]amino]-3-benzyl-2-oxo-1-pyrrolidineacetate
• CAS: 501380-91-2
• 化学式: C₂₄H₃₃N₃O₆
• 分子量: 459.543
• InChiKey: CAZJVYGKXVSXDS-UUOWRZLLSA-N

反应信息

• 作为反应物：
  描述：

  methyl 3(R)-[[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]carbonyl]amino]-3-benzyl-2-oxo-1-pyrrolidineacetate 在 氨 作用下， 以62%的产率得到3(R)-[[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]carbonyl]amino]-3-benzyl-2-oxo-1-pyrrolidineacetamide
  参考文献：
  名称：

  Synthesis and Dopamine Receptor Modulating Activity of 3-Substituted γ-Lactam Peptidomimetics of l-Prolyl-l-leucyl-glycinamide

  摘要：

  gamma-Lactam. peptidomimetic 2 of Pro-Leu-Gly-NH2 (PLG) was substituted at the 3-position with isobutyl, butyl, and benzyl moieties to give the PLG peptidomimetics 3-5, respectively. These compounds were synthesized to test the hypothesis that attaching a hydrophobic moiety to the lactam ring to mimic the isobutyl side chain of the leucyl residue of PLG would increase the dopamine receptor modulating activity of such peptidomimetics. These peptidomimetics were tested for their ability to enhance the binding of [H-3]-N-propylnorapomorphine to dopamine receptors isolated from bovine striatal membranes. The rank order of effectiveness of the 3-substituent was benzyl > n-butyl > isobutyl > H.

  DOI：

  10.1021/jm020441o
• 作为产物：
  描述：

  BOC-L-脯氨酸 、 methyl 3(R)-[N-(tert-butoxycarbonyl)amino]-3-benzyl-2-oxo-1-pyrrolidineacetate hydrochloride 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以0.97 g的产率得到methyl 3(R)-[[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]carbonyl]amino]-3-benzyl-2-oxo-1-pyrrolidineacetate
  参考文献：
  名称：

  Synthesis and Dopamine Receptor Modulating Activity of 3-Substituted γ-Lactam Peptidomimetics of l-Prolyl-l-leucyl-glycinamide

  摘要：

  gamma-Lactam. peptidomimetic 2 of Pro-Leu-Gly-NH2 (PLG) was substituted at the 3-position with isobutyl, butyl, and benzyl moieties to give the PLG peptidomimetics 3-5, respectively. These compounds were synthesized to test the hypothesis that attaching a hydrophobic moiety to the lactam ring to mimic the isobutyl side chain of the leucyl residue of PLG would increase the dopamine receptor modulating activity of such peptidomimetics. These peptidomimetics were tested for their ability to enhance the binding of [H-3]-N-propylnorapomorphine to dopamine receptors isolated from bovine striatal membranes. The rank order of effectiveness of the 3-substituent was benzyl > n-butyl > isobutyl > H.

  DOI：

  10.1021/jm020441o