D-aspartic acid β-tert-butyl ester α-[3-(trifluoromethyl)benzyl]amide | 512783-90-3

• 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: D-aspartic acid β-tert-butyl ester α-[3-(trifluoromethyl)benzyl]amide
• 英文别名: D-aspartic acid β-tert-butyl ester α-(3-trifluoromethyl)benzylamide；D-aspartic acid β-t-butyl ester α-(3-trifluoromethyl)benzylamide；D-aspartic acid β-t-butyl ester α-(3-trifluoromethylbenzyl)amide；D-aspartic acid γ-tert-butyl ester α-(3-trifluoromethyl-benzylamide)
• CAS: 512783-90-3
• 化学式: C₁₆H₂₁F₃N₂O₃
• 分子量: 346.35
• InChiKey: PZFCEQKCUZQGLN-GFCCVEGCSA-N

物化性质

• 沸点：
  473.0±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  24.0
• 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-[3-(trifluoromethyl)benzyl]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 (R)-N-(3-(trifluoromethyl)benzyl)-4-oxo-2-((3S,4R)-2-oxo-3-((S)-2-oxo-4-phenyloxazolidin-3-yl)-4-((E)-styryl)azetidin-1-yl)-4-(4-(2-(piperidin-1-yl)ethyl)piperidin-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：

  Cbz-D-天冬氨酸 4-叔丁酯一水物 在 palladium on activated charcoal N-羟基-7-氮杂苯并三氮唑 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 D-aspartic acid β-tert-butyl ester α-[3-(trifluoromethyl)benzyl]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

文献信息

• [EN] 3-SUBSTITUTED beta-LACTAMYL VASOPRESSIN V1A ANTAGONISTS<br/>[FR] ANTAGONISTES DE LA VASOPRESSINE V1A 20050421OJIMA ET AL.: "Asymmetric alkylations of a phenylalanylglycinate equivalent. Novel route to dipeptides bearing .alpha.-alkyl.alpha.-amino acid residues", J. AMERICAN CHEMICAL SOCIETY, vol. 112, no. 2, 1990, pages 770 - 774, XP002985507OJIMA ET AL.Asymmetric alkylations of a phenylalanylglycinate equivalent. Novel route to dipeptides bearing .alpha.-alkyl.alpha.-amino acid residuesJ. AMERICAN CHEMICAL SOCIETY19901122770774AAWO03031407A2SERENIX PHARMACEUTICALS LLC [US], et al20030417YYWO9730707A1LILLY CO ELI [US], et al19970828YY
  申请人：SERENIX PHARMACEUTICALS LLC

  公开号：WO2005035492A1

  公开（公告）日：2005-04-21

  Novel 2-(azetidin-2-on-1-yl)alkanedioic acids and derivatives thereof are described. Methods for using 2-(azetidin-2-on-l-yl)alkanedioic acids and derivatives thereof in the treatment of disease states responsive to antagonism of the vasopressin V1a receptor are also described.

  描述了小说2-(氮杂环丁烷-2-酮-1-基)烷二酸及其衍生物。还描述了在治疗对抗利尿素V1a受体有反应的疾病状态中使用2-(氮杂环丁烷-2-酮-1-基)烷二酸及其衍生物的方法。
• WO2007/109098
  申请人：——

  公开号：——

  公开（公告）日：——