[(R)-1-(1-Carbamoyl-cyclohexyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester | 223648-49-5

• 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: [(R)-1-(1-Carbamoyl-cyclohexyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(3R)-1-(1-carbamoylcyclohexyl)-2-oxopyrrolidin-3-yl]carbamate
• CAS: 223648-49-5
• 化学式: C₁₆H₂₇N₃O₄
• 分子量: 325.408
• InChiKey: XICVOKWOQZMLSN-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(R)-1-(1-Carbamoyl-cyclohexyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester 在 盐酸 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 benzyl (2S)-2-[[(3R)-1-(1-carbamoylcyclohexyl)-2-oxopyrrolidin-3-yl]carbamoyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and Dopamine Receptor Modulating Activity of Novel Peptidomimetics of l-Prolyl-l-leucyl-glycinamide Featuring α,α-Disubstituted Amino Acids

  摘要：

  In the present study, L-prolyl-L-leucyl-glycinamide (1) peptidomimetics 3a-3d and 4a-4d were synthesized utilizing alpha,alpha-disubstituted amino acids. These analogues were designed to explore the conformational effects of constraints at the phi(3) and psi(3) torsion angles. Constrained conformations were verified by the use of X-ray crystallography and circular dichroism. The effects of Pro-Leu-Gly-NH2 analogues 3a-3d and 4a-4d on enhancing rotational behavior induced by apomorphine in the 6-hydroxydopamine-lesioned animal models of Parkinson's disease were studied. The ability of these peptidomimetics to increase the binding of agonist N-propylnorapomorphine (NPA) to the dopamine D-2 receptor was also examined. Extended analogue Pro-Leu-Deg-NH2 was the most active compound of this series. It was 10 times more potent and almost 2 times more effective than 1 in increasing apomorphine-induced rotations (56 +/- 15% at 1.0 mg/kg ip) and in enhancing [H-3]NPA specific binding (40%).

  DOI：

  10.1021/jm980656r
• 作为产物：
  描述：

  1-(N-叔丁氧羰基氨基)环己烷甲酸 在 盐酸 、 4-二甲氨基吡啶 、 氨 、 sodium hydride 、 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 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 碘甲烷 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 生成 [(R)-1-(1-Carbamoyl-cyclohexyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and Dopamine Receptor Modulating Activity of Novel Peptidomimetics of l-Prolyl-l-leucyl-glycinamide Featuring α,α-Disubstituted Amino Acids

  摘要：

  In the present study, L-prolyl-L-leucyl-glycinamide (1) peptidomimetics 3a-3d and 4a-4d were synthesized utilizing alpha,alpha-disubstituted amino acids. These analogues were designed to explore the conformational effects of constraints at the phi(3) and psi(3) torsion angles. Constrained conformations were verified by the use of X-ray crystallography and circular dichroism. The effects of Pro-Leu-Gly-NH2 analogues 3a-3d and 4a-4d on enhancing rotational behavior induced by apomorphine in the 6-hydroxydopamine-lesioned animal models of Parkinson's disease were studied. The ability of these peptidomimetics to increase the binding of agonist N-propylnorapomorphine (NPA) to the dopamine D-2 receptor was also examined. Extended analogue Pro-Leu-Deg-NH2 was the most active compound of this series. It was 10 times more potent and almost 2 times more effective than 1 in increasing apomorphine-induced rotations (56 +/- 15% at 1.0 mg/kg ip) and in enhancing [H-3]NPA specific binding (40%).

  DOI：

  10.1021/jm980656r