tert-butyl 2-[[(2Z)-2-ethylidene-3-[[4-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]amino]phenyl]methylamino]-4-methylpentanoyl]amino]acetate | 1449280-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: tert-butyl 2-[[(2Z)-2-ethylidene-3-[[4-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]amino]phenyl]methylamino]-4-methylpentanoyl]amino]acetate
• CAS: 1449280-84-5
• 化学式: C₃₈H₄₆N₄O₆
• 分子量: 654.806
• InChiKey: GRGIYHCEMWJSCT-FEDGQQDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[[(2Z)-2-ethylidene-3-[[4-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]amino]phenyl]methylamino]-4-methylpentanoyl]amino]acetate 在 磷酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成
  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
• 作为产物：
  描述：

  在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 tert-butyl 2-[[(2Z)-2-ethylidene-3-[[4-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]amino]phenyl]methylamino]-4-methylpentanoyl]amino]acetate
  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.