(R)-2-[3-Benzyl-3-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-ureido]-4-methyl-pentanoic acid methyl ester | 853905-05-2

• 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: (R)-2-[3-Benzyl-3-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-ureido]-4-methyl-pentanoic acid methyl ester
• CAS: 853905-05-2
• 化学式: C₃₀H₄₃N₃O₆
• 分子量: 541.688
• InChiKey: RARVWDBODUOHND-JIMJEQGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  117.2
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-2-[3-Benzyl-3-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-ureido]-4-methyl-pentanoic acid methyl ester 在 lithium hydroxide 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 (R)-methyl 2-((R)-2-(3-benzyl-3-((2R,3S)-3-(tert-butoxycarbonyl)-2-hydroxy-4-phenylbutyl)ureido)-4-methylpentanamido)-3-methylbutanoate
  参考文献：
  名称：

  Stereochemical Analysis of (Hydroxyethyl)urea Peptidomimetic Inhibitors of γ-Secretase

  摘要：

  (Hydroxyethyl)urea peptidomimetics systematically altered at positions P2-P3' with hydrophobic D-amino acids were synthesized. An all D-amino acid containing analogue was identified that effectively blocked gamma-secretase activity in a cell-free system (IC50 = 30 nM). Systematic alteration of the stereocenters of a potent compound revealed interdependence between the various positions. Although typically less potent than their L-peptidomimetic counterparts. selected all D-amino acid containing analogues were equipotent. to their counterparts in a cell-based assay when incubated for extended times.

  DOI：

  10.1021/jm049566e
• 作为产物：
  描述：

  (R)-leucine methyl ester hydrochloride 在 碳酸氢钠 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.5h， 生成 (R)-2-[3-Benzyl-3-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-ureido]-4-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Stereochemical Analysis of (Hydroxyethyl)urea Peptidomimetic Inhibitors of γ-Secretase

  摘要：

  (Hydroxyethyl)urea peptidomimetics systematically altered at positions P2-P3' with hydrophobic D-amino acids were synthesized. An all D-amino acid containing analogue was identified that effectively blocked gamma-secretase activity in a cell-free system (IC50 = 30 nM). Systematic alteration of the stereocenters of a potent compound revealed interdependence between the various positions. Although typically less potent than their L-peptidomimetic counterparts. selected all D-amino acid containing analogues were equipotent. to their counterparts in a cell-based assay when incubated for extended times.

  DOI：

  10.1021/jm049566e