((1S,2S,4R)-1-Benzyl-2-hydroxy-4-{(S)-2-methyl-1-[(pyridin-4-ylmethyl)-carbamoyl]-propylcarbamoyl}-pentyl)-carbamic acid tert-butyl ester | 669083-16-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: ((1S,2S,4R)-1-Benzyl-2-hydroxy-4-{(S)-2-methyl-1-[(pyridin-4-ylmethyl)-carbamoyl]-propylcarbamoyl}-pentyl)-carbamic acid tert-butyl ester
• CAS: 669083-16-3
• 化学式: C₂₉H₄₂N₄O₅
• 分子量: 526.676
• InChiKey: GDXQPYKIIRNYKA-OCFYOKIWSA-N

物化性质

• 沸点：
  783.4±60.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  38.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  129.65
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ((1S,2S,4R)-1-Benzyl-2-hydroxy-4-{(S)-2-methyl-1-[(pyridin-4-ylmethyl)-carbamoyl]-propylcarbamoyl}-pentyl)-carbamic acid tert-butyl ester 在 盐酸 、 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 {1-[(S)-1-((1S,2S,4R)-1-Benzyl-2-hydroxy-4-{(S)-2-methyl-1-[(pyridin-4-ylmethyl)-carbamoyl]-propylcarbamoyl}-pentylcarbamoyl)-ethylcarbamoyl]-5,5,5-trifluoro-pentyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Phe*-Ala-based pentapeptide mimetics are BACE inhibitors: P2 and P3 SAR

  摘要：

  We describe herein the syntheses and evaluation of a series of C-termini pyridyl containing Phe*-Ala-based BACE inhibitors (5-19). In conjunction with four fixed residues at the P1 (Phe), P1' (Ala), P2' (Val), and P2' cap (Pyr.), rather detailed SAR modifications at P2 and P3 positions were pursued. The promising inhibitors emerging from this SAR investigation, 12 and 17 demonstrated very good enzyme potency (IC50 = 45 nM) and cellular activity (IC50 = 0.4 muM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.084
• 作为产物：
  描述：

  ((1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-{(S)-2-methyl-1-[(pyridin-4-ylmethyl)-carbamoyl]-propylcarbamoyl}-pentyl)-carbamic acid tert-butyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到((1S,2S,4R)-1-Benzyl-2-hydroxy-4-{(S)-2-methyl-1-[(pyridin-4-ylmethyl)-carbamoyl]-propylcarbamoyl}-pentyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Phe*-Ala-based pentapeptide mimetics are BACE inhibitors: P2 and P3 SAR

  摘要：

  We describe herein the syntheses and evaluation of a series of C-termini pyridyl containing Phe*-Ala-based BACE inhibitors (5-19). In conjunction with four fixed residues at the P1 (Phe), P1' (Ala), P2' (Val), and P2' cap (Pyr.), rather detailed SAR modifications at P2 and P3 positions were pursued. The promising inhibitors emerging from this SAR investigation, 12 and 17 demonstrated very good enzyme potency (IC50 = 45 nM) and cellular activity (IC50 = 0.4 muM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.084