N-<4-(4-hydroxyphenyl)butyryl>-L-proline | 86778-72-5

• 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: N-<4-(4-hydroxyphenyl)butyryl>-L-proline
• 英文别名: N-4-(4'-hydroxyphenyl)-butyryl-L-proline；N-4-(4-hydroxyphenyl)-butyryl-L-proline；(2S)-1-[4-(4-hydroxyphenyl)butanoyl]pyrrolidine-2-carboxylic acid
• CAS: 86778-72-5
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: VWPRVVOWEIYMRF-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<4-(4-hydroxyphenyl)butyryl>-L-proline 在 Pd-BaSO₄ N-乙基马来酰亚胺 、 sodium hydroxide 、 氢气 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 138.0h， 生成 N-[4-(4-hydroxyphenyl)butyryl]-L-prolyl-DL-α-methyltyrosyl-L-arginine
  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：

  L-脯氨酸苄酯盐酸盐 在 palladium on carbon N-乙基马来酰亚胺 、 氢气 、 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 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 20.0h， 生成 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

文献信息

• Renally active dipeptides
  申请人：SmithKline Beckman Corporation

  公开号：US04395401A1

  公开（公告）日：1983-07-26

  A group of prolyl-.alpha.-lower alkylphenylalanine dipeptides have been found to improve kidney function especially on cumulative administration. A species is N-4-(4'-hydroxyphenyl)-butyryl-L-propyl-D,L-.alpha.-methyl-3,4-dimethoxyph enylalanyl-L-arginine.

  一组脯氨酸-α-较低烷基苯丙氨酸二肽已被发现在累积使用时特别能改善肾功能。其中一种是N-4-(4'-羟基苯基)-丁酰-L-丙基-D，L-α-甲基-3,4-二甲氧基苯丙氨酰-L-精氨酸。
• 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：——
• 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