D-aspartic acid β-t-butyl ester α-[(R)-α-methylbenzyl]amide | 512785-16-9

• 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-t-butyl ester α-[(R)-α-methylbenzyl]amide
• 英文别名: tert-butyl(R)-3-amino-4-oxo-4-(((R)-1-phenylethyl)amino)butanoate；tert-butyl (3R)-3-amino-4-oxo-4-[[(1R)-1-phenylethyl]amino]butanoate
• CAS: 512785-16-9
• 化学式: C₁₆H₂₄N₂O₃
• 分子量: 292.378
• InChiKey: CJSCOSSNIAKAEL-DGCLKSJQSA-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-t-butyl ester α-[(R)-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
  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：

  2-Methyl-2-propanyl N~2~-[(benzyloxy)carbonyl]-N-[(1R)-1-phenylethyl]-D-alpha-asparaginate 以100的产率得到D-aspartic acid β-t-butyl ester α-[(R)-α-methylbenzyl]amide
  参考文献：
  名称：

  β-Lactamyl vasopressin V1a Antagonists

  摘要：

  本发明涉及2-(氮杂环丙酮-2-酮-1-基)脂肪二酸衍生物和2-(氮杂环丙酮-2-酮-1-基)烷氧基脂肪酸衍生物，用于治疗对抗加压素V1a受体有反应的疾病状态。

  公开号：

  US07119083B2

文献信息

• Synthesis and evaluation of potent and selective human V1a receptor antagonists as potential ligands for PET or SPECT imaging
  作者：Karine Fabio、Christophe Guillon、Carl J. Lacey、Shi-fang Lu、Ned D. Heindel、Craig F. Ferris、Michael Placzek、Graham Jones、Michael J. Brownstein、Neal G. Simon

  DOI：10.1016/j.bmc.2011.12.013

  日期：2012.2

  SRX246 is a potent, highly selective human vasopressin V1a antagonist that crosses the blood-brain barrier in rats. CNS penetration makes SRX246 an ideal candidate for potential radiolabeling and use in visualization and characterization of the role of the V1a receptor in multiple stress-related disorders. Before radiolabeling studies, cold reference analogs of SRX246 were prepared. This study describes the synthesis and in vitro screening for human V1a receptor binding and permeability of fluoro, iodo, and methyl reference compounds for SRX246 and the preparation of a tin precursor. For each compound, the potential utility of corresponding radiolabeled analogs for PET and SPECT imaging is discussed. (C) 2011 Elsevier Ltd. All rights reserved.