boc-dl-(4-pyrimidinyl)alanine | 108868-86-6

• 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: boc-dl-(4-pyrimidinyl)alanine
• 英文别名: 2-((tert-Butoxycarbonyl)amino)-3-(pyrimidin-4-yl)propanoic acid；2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-pyrimidin-4-ylpropanoic acid
• CAS: 108868-86-6
• 化学式: C₁₂H₁₇N₃O₄
• 分子量: 267.285
• InChiKey: PEDGWWWLDZOMMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  boc-dl-(4-pyrimidinyl)alanine 在 N-甲基吗啉 、 盐酸 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 ((S)-1-{1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(4-methyl-pentanoylamino)-butylcarbamoyl]-2-pyrimidin-4-yl-ethylcarbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Novel renin inhibitors containing analogs of statine retro-inverted at the C-termini. Specificity at the P2 histidine site

  摘要：

  Substituted 1,3- and 1,4-diamines were prepared from epoxides derived from Boc-leucine or Boc-cyclohexylalanine. These diamines were incorporated into renin inhibitors (IC50 = 4-1500 nM) replacing the Leu-Val scissile bond in small peptide analogues of angiotensinogen. Replacement of the P2 histidine imidazole with other heterocycles maintained or enhanced binding while changing the overall basicity of the inhibitor. Finally, substitution of O-methyltyrosine for the P3 phenylalanine suppressed chymotrypsin cleavage of the P3-P2 bond.

  DOI：

  10.1021/jm00390a018
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 dl-(4-pyrimidinyl)alanine 在 sodium hydroxide 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 16.0h， 以71%的产率得到boc-dl-(4-pyrimidinyl)alanine
  参考文献：
  名称：

  Novel renin inhibitors containing analogs of statine retro-inverted at the C-termini. Specificity at the P2 histidine site

  摘要：

  Substituted 1,3- and 1,4-diamines were prepared from epoxides derived from Boc-leucine or Boc-cyclohexylalanine. These diamines were incorporated into renin inhibitors (IC50 = 4-1500 nM) replacing the Leu-Val scissile bond in small peptide analogues of angiotensinogen. Replacement of the P2 histidine imidazole with other heterocycles maintained or enhanced binding while changing the overall basicity of the inhibitor. Finally, substitution of O-methyltyrosine for the P3 phenylalanine suppressed chymotrypsin cleavage of the P3-P2 bond.

  DOI：

  10.1021/jm00390a018

文献信息

• Novel renin inhibitors containing analogs of statine retro-inverted at the C-termini. Specificity at the P2 histidine site
  作者：Saul H. Rosenberg、Jacob J. Plattner、Keith W. Woods、Herman H. Stein、Patrick A. Marcotte、Jerome Cohen、Thomas J. Perun

  DOI：10.1021/jm00390a018

  日期：1987.7

  Substituted 1,3- and 1,4-diamines were prepared from epoxides derived from Boc-leucine or Boc-cyclohexylalanine. These diamines were incorporated into renin inhibitors (IC50 = 4-1500 nM) replacing the Leu-Val scissile bond in small peptide analogues of angiotensinogen. Replacement of the P2 histidine imidazole with other heterocycles maintained or enhanced binding while changing the overall basicity of the inhibitor. Finally, substitution of O-methyltyrosine for the P3 phenylalanine suppressed chymotrypsin cleavage of the P3-P2 bond.