ethyl 2-[[(3S)-3-amino-2-hydroxy-4-phenylbutanoyl]amino]acetate | 209174-43-6

• 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: ethyl 2-[[(3S)-3-amino-2-hydroxy-4-phenylbutanoyl]amino]acetate
• CAS: 209174-43-6
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: WEYHDGPGHQGNPT-AMGKYWFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  101.65
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-[[(3S)-3-amino-2-hydroxy-4-phenylbutanoyl]amino]acetate 在 palladium on activated charcoal 二氯乙酸 、 碳酸二异丙酯 、 氢气 、 1-羟基苯并三唑 、 二甲基亚砜 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 乙醇 、 水 、 溶剂黄146 、 甲苯 、 乙腈 为溶剂， 反应 2.0h， 生成 ((S)-3-{2-[((R)-5-Guanidino-2-phenylmethanesulfonylamino-pentanoyl)-methyl-amino]-acetylamino}-2-oxo-4-phenyl-butyrylamino)-acetic acid ethyl ester
  参考文献：
  名称：

  Novel, potent and selective chimeric FXa inhibitors featuring hydrophobic p1-ketoamide moieties

  摘要：

  Judicious combination of P-region sequences of highly potent anticoagulant proteins including NAPS, NAP6, Ecotin, and Antistasin with SAR from small molecule FXa inhibitors led to a series of chimeric inhibitors of formula 1a-j. We report herein the design, synthesis, and biological activity of this novel family of FXa inhibitors that express both high in vitro potency and superb selectivity against related serine proteases. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00458-3
• 作为产物：
  描述：

  Fmoc-Phe-H 在 吡啶 、 二乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl 2-[[(3S)-3-amino-2-hydroxy-4-phenylbutanoyl]amino]acetate
  参考文献：
  名称：

  Novel, potent and selective chimeric FXa inhibitors featuring hydrophobic p1-ketoamide moieties

  摘要：

  Judicious combination of P-region sequences of highly potent anticoagulant proteins including NAPS, NAP6, Ecotin, and Antistasin with SAR from small molecule FXa inhibitors led to a series of chimeric inhibitors of formula 1a-j. We report herein the design, synthesis, and biological activity of this novel family of FXa inhibitors that express both high in vitro potency and superb selectivity against related serine proteases. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00458-3

文献信息

• Analogues of substance P containing an α-hydroxy, β-amino acid: synthesis and biological activity
  作者：A Ewenson、R Laufer、M Chorev、Z Selinger、C Gilon

  DOI：10.1016/0223-5234(91)90104-u

  日期：1991.6

  Several bestatin-like analogues of pGlu6-Phe7-Phe8-Gly9-Leu10-Met11-NH2, a C-terminal hexapeptide derived from substance P (SP), an endogenous mammalian neuropeptide, were prepared. In this sequence [pGlu6]SP(6-11), Phe7 or Phe8 were substituted by the amino acid. (R,S)-alpha-hydroxy, (S)-beta-amino, 4-phenylbutyfic acid (AHPA). Several key diastereomeric products were resolved by selective precipitation from the reaction mixture and the resolved components were characterized by chromatography. FAB-mass spectrometry and amino acid analysis. The inhibitory potency of these peptides on SP degradation in rat diencephalon preparations was assayed. It was found that one of the resolved diastereomeric analogues, [pGlu6, AHPA8]SP(6-11) (9a) was a potent inhibitor of SP degradation with an IC50 of 20-mu-M. The analogues prepared in this study were devoid of spasmogenic activity on the guinea-pig ileum assay.