N-<4-(4-hydroxyphenyl)butyryl>-L-proline benzyl ester | 86778-71-4

• 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: N-<4-(4-hydroxyphenyl)butyryl>-L-proline benzyl ester
• 英文别名: benzyl (2S)-1-[4-(4-hydroxyphenyl)butanoyl]pyrrolidine-2-carboxylate
• CAS: 86778-71-4
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: HYBMFUDKHVNBHM-FQEVSTJZSA-N

物化性质

• 沸点：
  572.3±50.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<4-(4-hydroxyphenyl)butyryl>-L-proline benzyl ester 在 palladium on carbon 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以100%的产率得到N-<4-(4-hydroxyphenyl)butyryl>-L-proline
  参考文献：
  名称：

  Tri- and tetrapeptide analogs of kinins as potential renal vasodilators

  摘要：

  Tri- and tetrapeptide analogues were synthesized and evaluated as renal vasodilators. These peptides were prepared by standard coupling reactions, which also provided good yields with hindered alpha-methyl amino acid derivatives. Preliminary evidence of renal vasodilator activity was determined in anesthetized dogs by measuring the effects on renal blood flow and calculating the accompanying changes in renal vascular resistance. The most potent compounds contained, in their basic structure, the L-prolyl-DL-alpha-methylphenylalanyl-L-arginine and L-prolyl-DL-alpha-methylphenylalanylglycyl-L-proline arrays. Substitution on the N-terminal proline with 4-phenylbutyryl and 4-(4-hydroxyphenyl)butyryl side chains produced enhanced renal vasodilator activity and, in certain cases, selectivity for the renal vasculature.

  DOI：

  10.1021/jm00369a017
• 作为产物：
  描述：

  4-羟基苯丁酸甲酯 在 N-乙基马来酰亚胺 、 氢溴酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 N-<4-(4-hydroxyphenyl)butyryl>-L-proline benzyl ester
  参考文献：
  名称：

  Tri- and tetrapeptide analogs of kinins as potential renal vasodilators

  摘要：

  Tri- and tetrapeptide analogues were synthesized and evaluated as renal vasodilators. These peptides were prepared by standard coupling reactions, which also provided good yields with hindered alpha-methyl amino acid derivatives. Preliminary evidence of renal vasodilator activity was determined in anesthetized dogs by measuring the effects on renal blood flow and calculating the accompanying changes in renal vascular resistance. The most potent compounds contained, in their basic structure, the L-prolyl-DL-alpha-methylphenylalanyl-L-arginine and L-prolyl-DL-alpha-methylphenylalanylglycyl-L-proline arrays. Substitution on the N-terminal proline with 4-phenylbutyryl and 4-(4-hydroxyphenyl)butyryl side chains produced enhanced renal vasodilator activity and, in certain cases, selectivity for the renal vasculature.

  DOI：

  10.1021/jm00369a017

文献信息

• Renally active tetrapeptides
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0086660A2

  公开（公告）日：1983-08-24

  N-Acyltetrapeptides are described which are active in improving renal function. An exemplary species is N-4-(4-hydroxyphenyl)-butyryl-L- prolyl-D,L-α-methyl-phenylalanyl--glycyl-L-proline.

  N-酰基四肽在改善肾功能方面具有活性。N-4-（4-羟基苯基）-丁酰基-L-脯氨酰-D,L-α-甲基-苯丙氨酰-甘氨酰-L-脯氨酸就是其中的一种。
• PFEIFFER, F. R.
  作者：PFEIFFER, F. R.

  DOI：——

  日期：——
• Renally active dipeptides
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0074787B1

  公开（公告）日：1985-03-27
• US4395401A
  申请人：——

  公开号：US4395401A

  公开（公告）日：1983-07-26
• US4386075A
  申请人：——

  公开号：US4386075A

  公开（公告）日：1983-05-31