phenylacetyl-Arg-Val-Arg-4-amidinobenzylamide | 1206473-15-5

• 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: phenylacetyl-Arg-Val-Arg-4-amidinobenzylamide
• 英文别名: Phac-Arg-Val-Arg-4-Amba；(2S)-N-[(2S)-1-[[(2S)-1-[(4-carbamimidoylphenyl)methylamino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]-5-(diaminomethylideneamino)-2-[(2-phenylacetyl)amino]pentanamide
• CAS: 1206473-15-5
• 化学式: C₃₃H₅₀N₁₂O₄
• 分子量: 678.838
• InChiKey: YGMAIAXBJLVVLI-KLJDGLGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  49
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  295
• 氢给体数：
  10
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 水 、 三氟乙酸 作用下， 反应 3.0h， 生成 phenylacetyl-Arg-Val-Arg-4-amidinobenzylamide
  参考文献：
  名称：

  New substrate analogue furin inhibitors derived from 4-amidinobenzylamide

  摘要：

  A series of new peptidomimetic furin inhibitors was synthesized, which was derived from our previously described lead structure phenylacetyl-Arg-Val-Arg-4-amidinobenzylamide (1). Substitution of Val by other amino acid residues revealed several highly potent furin inhibitors with K(i) values of less than 2 nM, containing guanidinoalanine, Ile, Phe or Tyr in the P3 position. The replacement of the P2 Arg by Lys was also well accepted, whereas the incorporation of D-amino acids at various positions resulted in poor inhibitors. The use of the 4-amidinobenzylamide group provides convenient synthetic access to stable proprotein convertase inhibitors and derivatives as biochemical tools and for further studies in cell culture. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.091

文献信息

• [DE] N-TERMINAL MODIFIZIERTE TETRAPEPTIDDERIVATE MIT C-TERMINALEM ARGININMIMETIKUM<br/>[EN] N-TERMINALLY MODIFIED TETRAPEPTIDE DERIVATIVES HAVING A C-TERMINAL ARGININE MIMETIC<br/>[FR] DÉRIVÉ TÉTRAPEPTIDIQUE MODIFIÉ EN POSITION N-TERMINALE AVEC UN MIMÉTIQUE D'ARGININE EN POSITION C-TERMINALE
  申请人：UNIV MARBURG PHILIPPS

  公开号：WO2010048941A2

  公开（公告）日：2010-05-06

  Die Erfindung betrifft multibasische, N-terminal modifizierte Tetrapeptidmimetika mit einem C-terminalen P1-Argininmimetikum, Verfahren zu deren Herstellung und Verwendung zur Therapie und Prophylaxe von Erkrankungen, hervorgerufen durch bakterielle Erreger oder Viren, sowie zur Therapie und Prophylaxe von Diabetes, Arteriosklerose, Krebs, Alzheimer oder der Ausbildung von Übergewicht, sowie die Verwendung dieser Verbindungen als Hemmstoffe der Proproteinkonvertasen die hinter basischen P1-Resten spalten, speziell zur Hemmung der Protease Furin.
• New substrate analogue furin inhibitors derived from 4-amidinobenzylamide
  作者：Gero L. Becker、Kornelia Hardes、Torsten Steinmetzer

  DOI：10.1016/j.bmcl.2011.06.091

  日期：2011.8

  A series of new peptidomimetic furin inhibitors was synthesized, which was derived from our previously described lead structure phenylacetyl-Arg-Val-Arg-4-amidinobenzylamide (1). Substitution of Val by other amino acid residues revealed several highly potent furin inhibitors with K(i) values of less than 2 nM, containing guanidinoalanine, Ile, Phe or Tyr in the P3 position. The replacement of the P2 Arg by Lys was also well accepted, whereas the incorporation of D-amino acids at various positions resulted in poor inhibitors. The use of the 4-amidinobenzylamide group provides convenient synthetic access to stable proprotein convertase inhibitors and derivatives as biochemical tools and for further studies in cell culture. (C) 2011 Elsevier Ltd. All rights reserved.