(S)-2-[(2S,3R)-2-((R)-2-Carbamoyl-pyrrolidine-1-carbonyl)-3-methyl-pyrrolidine-1-carbonyl]-pyrrolidine-1-carboxylic acid tert-butyl ester | 247219-85-8

• 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: (S)-2-[(2S,3R)-2-((R)-2-Carbamoyl-pyrrolidine-1-carbonyl)-3-methyl-pyrrolidine-1-carbonyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-[(2S,3R)-2-[(2R)-2-carbamoylpyrrolidine-1-carbonyl]-3-methylpyrrolidine-1-carbonyl]pyrrolidine-1-carboxylate
• CAS: 247219-85-8
• 化学式: C₂₁H₃₄N₄O₅
• 分子量: 422.525
• InChiKey: QXXIQJGMMHDRKO-WCVJEAGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-[(2S,3R)-2-((R)-2-Carbamoyl-pyrrolidine-1-carbonyl)-3-methyl-pyrrolidine-1-carbonyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 Pro-Pro(cis-3-Me)-D-Pro-NH2*HCl
  参考文献：
  名称：

  Synthesis and dopamine receptor modulating activity of unsubstituted and substituted triproline analogues of l-prolyl-l-leucyl-glycinamide (PLG)

  摘要：

  Triprolines Pro-Pro-Pro-NH2 (4), Pro-Pro-D-Pro-NH2 (5), Pro-Pro(trans-3-Me)-D-Pro-NH2 (6), and Pro-Pro(cis-3-Me)-D-Pro-NH2 (7) were made as conformationally constrained analogues of Pro-Leu-Gly-NH2. Triprolines 4-6 produced significant increases in the high- and low-affinity state ratio (R-H/R-L) of the dopamine receptor, but only 4 was found to increase apomorphine induced rotations in 6-hydroxydopamine-lesioned rats. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00386-8
• 作为产物：
  描述：

  D-脯氨酰胺 在 盐酸 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 (S)-2-[(2S,3R)-2-((R)-2-Carbamoyl-pyrrolidine-1-carbonyl)-3-methyl-pyrrolidine-1-carbonyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and dopamine receptor modulating activity of unsubstituted and substituted triproline analogues of l-prolyl-l-leucyl-glycinamide (PLG)

  摘要：

  Triprolines Pro-Pro-Pro-NH2 (4), Pro-Pro-D-Pro-NH2 (5), Pro-Pro(trans-3-Me)-D-Pro-NH2 (6), and Pro-Pro(cis-3-Me)-D-Pro-NH2 (7) were made as conformationally constrained analogues of Pro-Leu-Gly-NH2. Triprolines 4-6 produced significant increases in the high- and low-affinity state ratio (R-H/R-L) of the dopamine receptor, but only 4 was found to increase apomorphine induced rotations in 6-hydroxydopamine-lesioned rats. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00386-8