3-[[[3-(Diaminomethylideneamino)benzoyl]amino]carbamoylamino]-3-(4-methoxycarbonylphenyl)propanoic acid;hydrochloride | 1401717-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[[[3-(Diaminomethylideneamino)benzoyl]amino]carbamoylamino]-3-(4-methoxycarbonylphenyl)propanoic acid;hydrochloride
• 英文别名: 3-[[[3-(diaminomethylideneamino)benzoyl]amino]carbamoylamino]-3-(4-methoxycarbonylphenyl)propanoic acid;hydrochloride
• CAS: 1401717-35-8
• 化学式: C₂₀H₂₂N₆O₆*ClH
• 分子量: 478.892
• InChiKey: AINKMSVEEKXFJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  198
• 氢给体数：
  7
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-甲酰基苯甲酸苄酯 在 2,4,6-三甲基吡啶 、 三异丙基硅烷 、 palladium on activated charcoal 、 ammonium acetate 、 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， -10.0~60.0 ℃ 、100.0 kPa 条件下， 反应 29.25h， 生成 3-[[[3-(Diaminomethylideneamino)benzoyl]amino]carbamoylamino]-3-(4-methoxycarbonylphenyl)propanoic acid;hydrochloride
  参考文献：
  名称：

  Scalable synthesis of an integrin-binding peptide mimetic for biomedical applications

  摘要：

  A scalable, solution-phase synthesis of the selectively protected non-peptide RGD (arginine-glycine-aspartic acid) mimetic 6 is described. This synthesis serves as an alternative to the previously described solid-phase synthesis of this compound, thereby making this important integrin-binding mimetic readily accessible. The free carboxylic acid of 6 was conjugated to a protected diamine, followed by global deprotection to give a derivative 27, suitable for immobilization onto amine-reactive surfaces. The RGD mimetic 28 demonstrated superior biological activity in comparison to a native linear RGD peptide and the semi-synthetic cyclic cRGDfK peptide in a cell attachment inhibition assay. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.002

文献信息

• Scalable synthesis of an integrin-binding peptide mimetic for biomedical applications
  作者：Andrew G. Riches、Teresa Cablewski、Veronica Glattauer、Helmut Thissen、Laurence Meagher

  DOI：10.1016/j.tet.2012.09.002

  日期：2012.11

  A scalable, solution-phase synthesis of the selectively protected non-peptide RGD (arginine-glycine-aspartic acid) mimetic 6 is described. This synthesis serves as an alternative to the previously described solid-phase synthesis of this compound, thereby making this important integrin-binding mimetic readily accessible. The free carboxylic acid of 6 was conjugated to a protected diamine, followed by global deprotection to give a derivative 27, suitable for immobilization onto amine-reactive surfaces. The RGD mimetic 28 demonstrated superior biological activity in comparison to a native linear RGD peptide and the semi-synthetic cyclic cRGDfK peptide in a cell attachment inhibition assay. (C) 2012 Elsevier Ltd. All rights reserved.