N-(1-adamantylacetyl)-L-proline | 87113-92-6

• 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-(1-adamantylacetyl)-L-proline
• 英文别名: N-(1-Adamantyl)-ethanoyl-L-proline；(2S)-1-[2-(1-adamantyl)acetyl]pyrrolidine-2-carboxylic acid
• CAS: 87113-92-6
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: YMRJLHIMXQEODL-ZZTKBFGJSA-N

物化性质

• 沸点：
  492.1±38.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(1-adamantylacetyl)-L-proline 在 N-乙基马来酰亚胺 、 sodium hydroxide 、 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 、 甲醇 为溶剂， 生成 N-(1-adamantylacetyl)-L-prolyl-DL-α-methylphenylalanyl-N^ω-nitro-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 activated charcoal 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 为溶剂， 生成 N-(1-adamantylacetyl)-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

• Adamantyl containing peptides
  申请人：SmithKline Beckman Corporation

  公开号：US04387049A1

  公开（公告）日：1983-06-07

  A group of adamantyl containing di- and tripeptides have been found to improve kidney function. A representative species of this group is N-(1-adamantyl)ethanoyl-L-proline-D,L-.alpha.-methylphenylalanyl-L-arginin e together with its salts.

  一组含有金刚烷基的二肽和三肽已被发现可以改善肾功能。该组的代表物种是N-(1-金刚烷基)乙酰-L-脯氨酸-D，L-α-甲基苯丙氨酰-L-精氨酸及其盐。
• PFEIFFER, F. R.
  作者：PFEIFFER, F. R.

  DOI：——

  日期：——
• US4387049A
  申请人：——

  公开号：US4387049A

  公开（公告）日：1983-06-07
• US4448972A
  申请人：——

  公开号：US4448972A

  公开（公告）日：1984-05-15