benzyl N-[(2-phenyl)ethyl]-glycinate | 65940-18-3

• 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: benzyl N-[(2-phenyl)ethyl]-glycinate
• 英文别名: N-phenethylglycine benzyl ester；benzyl 2-(2-phenylethylamino)acetate
• CAS: 65940-18-3
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: VNAKTYKWSBTUSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2-phenyl)ethyl]-glycinate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 25.0 ℃ 、296.47 kPa 条件下， 反应 39.0h， 生成 N-(tert-butoxycarbonyl)-N-phenethylglycine
  参考文献：
  名称：

  Bradykinin Receptor Antagonists Containing N-Substituted Amino Acids:  In Vitro and in Vivo B₂ and B₁ Receptor Antagonist Activity

  摘要：

  We report a systematic probing of the structural requirements of the bradykinin (BK) type 2 (B-2) receptor for antagonist activity by incorporating N-Alkyl-amino acid residues at positions 7 and 8 of a potent antagonist sequence. Compound 1 (D-Arg(0)-Arg(1)-Pro(2)-Hyp(3)-Gly(4)-Thi(5)-Ser(6)- D-Tic(7)-N-Chg(8)-Arg(9), CP-0597)(1,2) is a potent (pA(2) = 9.3, rat uterus; pK(i) = 9.62, binding, human receptor clone) Bz receptor antagonist devoid of in vitro B-1 antagonist activity (rabbit aorta). Compound 1 exhibits high potency (ED(50) = 29.2 pmol/kg/min, iv, rabbit) and duration of action when tested in models for in vivo B-2 antagonist activity. Although devoid of activity in a classic B-1 isolated tissue assay, B-1 antagonist activity for 1 was demonstrated in vivo, in a LPS-treated, inducible BK1 receptor rabbit blood pressure model (ED(50) = 1.7 nmol/kg/min). D-Arg(0) of 1 can be formally replaced by an achiral arginine surrogate, without significant loss in antagonist potency on rat uterus (compound 11, B-2 pA(2) = 9.1). Antagonist 13 (Hyp(2), NChg(8)), pK(i) = 10.2, and agonist 4 (N-methylcyclohexyl-Gly(8)), pK(i) = 10.1, also exhibited substantial binding to guinea pig ileum membrane receptors as well as a human Bz receptor clone. Very minor structural changes in the N-alkyl amino acid residues in positions 7 and 8 can modify the activity of this class of compounds from being extremely potent antagonists to tight binding partial or full agonists. These studies have resulted in a series of compounds containing inexpensive amino acid residues but which produce broad spectrum BK receptor blocking potency and exceptional in vivo duration of action.

  DOI：

  10.1021/jm950716i
• 作为产物：
  描述：

  甘氨酸苄酯盐酸盐 、 乙基溴苯 在 碳酸氢钠 作用下， 以 正己烷 、 乙酸乙酯 、 乙腈 为溶剂， 以38%的产率得到benzyl N-[(2-phenyl)ethyl]-glycinate
  参考文献：
  名称：

  US6060462

  摘要：

  公开号：

文献信息

• Bradykinin antagonist peptides incorporating N-substituted glycines
  申请人：Cortech, Inc.

  公开号：US05700779A1

  公开（公告）日：1997-12-23

  The present invention provides bradykinin type peptides containing N-substituted glycines, particularly bradykinin antagonist peptides useful for the treatment of conditions mediated by bradykinin including pain and inflammation.

  本发明提供了含有N-取代甘氨酸的激肽类肽段，特别是用于治疗由激肽介导的疾病，包括疼痛和炎症的激肽拮抗肽段。
• DE2801478
  申请人：——

  公开号：——

  公开（公告）日：——
• US06060462
  申请人：——

  公开号：——

  公开（公告）日：——
• ELECTROPHILIC PEPTIDE ANALOGS AS INHIBITORS OF TRYPSIN-LIKE ENZYMES
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0724446A1

  公开（公告）日：1996-08-07
• EP0724446A4
  申请人：——

  公开号：EP0724446A4

  公开（公告）日：1998-01-07