3(R)-[[1-(benzyloxycarbonyl)-2(S)-pyrrolidinylmethyl]amino]-2-oxo-1-pyrrolidineacetamide | 644996-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3(R)-[[1-(benzyloxycarbonyl)-2(S)-pyrrolidinylmethyl]amino]-2-oxo-1-pyrrolidineacetamide
• CAS: 644996-21-4
• 化学式: C₁₉H₂₆N₄O₄
• 分子量: 374.44
• InChiKey: CJUVAJZZAIDRIS-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  104.97
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3(R)-[[1-(benzyloxycarbonyl)-2(S)-pyrrolidinylmethyl]amino]-2-oxo-1-pyrrolidineacetamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以15%的产率得到3(R)-[[2(S)-pyrrolidinylmethyl]amino]-2-oxo-1-pyrrolidineacetamide
  参考文献：
  名称：

  iso-Lactam and reduced amide analogues of the peptidomimetic dopamine receptor modulator 3(R)-[(2(S)-Pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide

  摘要：

  An analogue of the highly potent gamma-lactam Pro-Leu-Gly-NH2 peptidomimetic, 3(R)-[(2(S)-pyrrolidinylcarbonyl) amino]-2-oxo-1-pyrrolidineacetamide (2), 4(R)-[[2(S)-pyrrolidinylcarbonyl]amino]-2-oxo-1-pyrrolidineacetamide (3), in which the lactam carbonyl moiety has been placed in a different position with respect to the 3-amino group was synthesized. Also, a series of analogues of 2, compounds 4-6, were synthesized in which each of the amide bonds of 2 were systematically replaced with a reduced amide bond surrogate. The analogues were tested for their ability to enhance the binding of [H-3]N-propylnorapomorphine to dopamine receptors in a functional in vitro assay utilizing bovine striatal membranes. Peptidomimetic 3 was shown to be more potent than 2, while 4 and 5 were significantly less effective than 2. Peptidomimetic 6 had a pharmacological profile similar to that of 2. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00396-1
• 作为产物：
  描述：

  methyl 3(R)-[[1-(benzyloxycarbonyl)-2(S)-pyrrolidinylmethyl]amino]-2-oxo-1-pyrrolidineacetate 在 氨 作用下， 以 甲醇 为溶剂， 以86%的产率得到3(R)-[[1-(benzyloxycarbonyl)-2(S)-pyrrolidinylmethyl]amino]-2-oxo-1-pyrrolidineacetamide
  参考文献：
  名称：

  iso-Lactam and reduced amide analogues of the peptidomimetic dopamine receptor modulator 3(R)-[(2(S)-Pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide

  摘要：

  An analogue of the highly potent gamma-lactam Pro-Leu-Gly-NH2 peptidomimetic, 3(R)-[(2(S)-pyrrolidinylcarbonyl) amino]-2-oxo-1-pyrrolidineacetamide (2), 4(R)-[[2(S)-pyrrolidinylcarbonyl]amino]-2-oxo-1-pyrrolidineacetamide (3), in which the lactam carbonyl moiety has been placed in a different position with respect to the 3-amino group was synthesized. Also, a series of analogues of 2, compounds 4-6, were synthesized in which each of the amide bonds of 2 were systematically replaced with a reduced amide bond surrogate. The analogues were tested for their ability to enhance the binding of [H-3]N-propylnorapomorphine to dopamine receptors in a functional in vitro assay utilizing bovine striatal membranes. Peptidomimetic 3 was shown to be more potent than 2, while 4 and 5 were significantly less effective than 2. Peptidomimetic 6 had a pharmacological profile similar to that of 2. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00396-1