D-aspartic acid β-tert-butyl ester α-[(S)-α-methylbenzyl]amide | 512785-15-8

• 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: D-aspartic acid β-tert-butyl ester α-[(S)-α-methylbenzyl]amide
• 英文别名: D-aspartic acid β-t-butyl ester α-[(S)-α-methyl]benzylamide；D-aspartic acid β-t-butyl ester α-[(S)-α-methylbenzyl]amide；D-aspartic acid γ-tert-butyl ester α-((S)-α-methyl-benzylamide)；D-aspartic acid β-tert-butyl ester α-[(S)-α-methyl]benzylamide
• CAS: 512785-15-8
• 化学式: C₁₆H₂₄N₂O₃
• 分子量: 292.378
• InChiKey: CJSCOSSNIAKAEL-WCQYABFASA-N

物化性质

• 沸点：
  472.3±45.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.42
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  D-aspartic acid β-tert-butyl ester α-[(S)-α-methylbenzyl]amide 在 甲酸 、 N-羟基-7-氮杂苯并三氮唑 、 magnesium sulfate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2R)-4-oxo-2-[(3S,4R)-2-oxo-3-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]-4-[(E)-2-phenylethenyl]azetidin-1-yl]-N-[(1S)-1-phenylethyl]-4-(4-piperidin-1-ylpiperidin-1-yl)butanamide
  参考文献：
  名称：

  Azetidinones as vasopressin V1a antagonists

  摘要：

  The azetidinone LY307174 (1) was identified as a screening lead for the vasopressin V1a receptor (IC50 45 nM at the human V1a receptor) based on molecular similarity to ketoconazole (2), a known antagonist of the luteinizing hormone releasing hormone receptor. Structure-activity relationships for the series were explored to optimize receptor affinity and pharmacokinetic properties, resulting in compounds with K-i values < 1 nM and brain levels after oral dosing similar to 100-fold higher than receptor affinities.[GRAPHICS](c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.031
• 作为产物：
  描述：

  N-[(benzyloxy)carbonyl]-D-aspartic acid β-tert-butyl ester α-[(S)-α-methylbenzyl]amide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以90%的产率得到D-aspartic acid β-tert-butyl ester α-[(S)-α-methylbenzyl]amide
  参考文献：
  名称：

  Azetidinones as vasopressin V1a antagonists

  摘要：

  The azetidinone LY307174 (1) was identified as a screening lead for the vasopressin V1a receptor (IC50 45 nM at the human V1a receptor) based on molecular similarity to ketoconazole (2), a known antagonist of the luteinizing hormone releasing hormone receptor. Structure-activity relationships for the series were explored to optimize receptor affinity and pharmacokinetic properties, resulting in compounds with K-i values < 1 nM and brain levels after oral dosing similar to 100-fold higher than receptor affinities.[GRAPHICS](c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.031