2-[(5Z)-3-[[4-[(2-aminoacetyl)amino]phenyl]methyl]-5-ethylidene-2,6-dioxo-4-propan-2-yl-1,3-diazinan-1-yl]acetic acid | 1449280-82-3

• 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: 2-[(5Z)-3-[[4-[(2-aminoacetyl)amino]phenyl]methyl]-5-ethylidene-2,6-dioxo-4-propan-2-yl-1,3-diazinan-1-yl]acetic acid
• CAS: 1449280-82-3
• 化学式: C₂₀H₂₆N₄O₅
• 分子量: 402.45
• InChiKey: PHAATYRRJDAOHG-TVPGTPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  tert-butyl 2-[(5Z)-5-ethylidene-3-[[4-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]phenyl]methyl]-2,6-dioxo-4-propan-2-yl-1,3-diazinan-1-yl]acetate 在 磷酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 2-[(5Z)-3-[[4-[(2-aminoacetyl)amino]phenyl]methyl]-5-ethylidene-2,6-dioxo-4-propan-2-yl-1,3-diazinan-1-yl]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.