2-[[(2E)-3-[(4-aminophenyl)methylamino]-2-ethylidene-4-methylpentanoyl]amino]acetic acid | 1449280-97-0

• 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: 2-[[(2E)-3-[(4-aminophenyl)methylamino]-2-ethylidene-4-methylpentanoyl]amino]acetic acid
• CAS: 1449280-97-0
• 化学式: C₁₇H₂₅N₃O₃
• 分子量: 319.404
• InChiKey: OPZIEWUCAYKXKA-LNKIKWGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl 2-[[3-[(4-aminophenyl)methylamino]-2-ethylidene-4-methylpentanoyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetate 在 磷酸 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 2-[[(2Z)-3-[(4-aminophenyl)methylamino]-2-ethylidene-4-methylpentanoyl]amino]acetic acid 、 2-[[(2E)-3-[(4-aminophenyl)methylamino]-2-ethylidene-4-methylpentanoyl]amino]acetic acid
  参考文献：
  名称：

  Modulation of αvβ3- and α5β1-integrin-mediated adhesion by dehydro-β-amino acids containing peptidomimetics

  摘要：

  A novel class of low molecular weight ligands of alpha(v)beta(3) and alpha(5)beta(1) integrins, that possess a dehydro-beta-amino acid as conformationally constrained core, linked to the pharmacophoric moieties mimicking the RGD recognition sequence, have been synthesized through a very simple protocol. Cell adhesion assays and integrin-mediated signaling activation experiments suggested a good affinity of these compounds toward both integrin receptors. Moreover, further elongation with two glycine units allowed to obtain an excellent dual inhibitor. Structural models for alpha(v)beta(3) integrin-ligand binding confirmed that the dehydro-beta-amino derivatives are able to act as an electrostatic clamp by establishing several stabilizing interactions with the receptor. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.050

文献信息

• Modulation of αvβ3- and α5β1-integrin-mediated adhesion by dehydro-β-amino acids containing peptidomimetics
  作者：Alessandra Tolomelli、Monica Baiula、Laura Belvisi、Angelo Viola、Luca Gentilucci、Stefano Troisi、Samantha Deianira Dattoli、Santi Spampinato、Monica Civera、Eusebio Juaristi、Margarita Escudero

  DOI：10.1016/j.ejmech.2013.05.050

  日期：2013.8

  A novel class of low molecular weight ligands of alpha(v)beta(3) and alpha(5)beta(1) integrins, that possess a dehydro-beta-amino acid as conformationally constrained core, linked to the pharmacophoric moieties mimicking the RGD recognition sequence, have been synthesized through a very simple protocol. Cell adhesion assays and integrin-mediated signaling activation experiments suggested a good affinity of these compounds toward both integrin receptors. Moreover, further elongation with two glycine units allowed to obtain an excellent dual inhibitor. Structural models for alpha(v)beta(3) integrin-ligand binding confirmed that the dehydro-beta-amino derivatives are able to act as an electrostatic clamp by establishing several stabilizing interactions with the receptor. (C) 2013 Elsevier Masson SAS. All rights reserved.