(S)-E-tert-butyl 3-(N-allyl-3-methoxy-3-oxopropanamido)-2-ethylidene-4-methylpentanoate | 1334125-67-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (S)-E-tert-butyl 3-(N-allyl-3-methoxy-3-oxopropanamido)-2-ethylidene-4-methylpentanoate
• CAS: 1334125-67-5
• 化学式: C₁₉H₃₁NO₅
• 分子量: 353.459
• InChiKey: NPEZGMUKDNPIIH-SHRNQRGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  丙二酸甲酯酰氯 、 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (S)-E-tert-butyl 3-(N-allyl-3-methoxy-3-oxopropanamido)-2-ethylidene-4-methylpentanoate 、 (S)-Z-tert-butyl 3-(N-allyl-3-methoxy-3-oxopropanamido)-2-ethylidene-4-methylpentanoate
  参考文献：
  名称：

  Dehydro-β-proline Containing α₄β₁ Integrin Antagonists: Stereochemical Recognition in Ligand–Receptor Interplay

  摘要：

  A novel class of dehydro-beta-proline-containing peptidomimetics, designed to be effective as alpha(4)beta(1) integrin ligands, has been developed on the basis of the fundamental requirements for the interactions of these transmembrane receptors with bioactive ligands. Dehydro-beta-proline ring has been synthesized through an original pathway, involving ring closing metathesis of a diallylamino derivative. The synthesized products showed to be effective and selective as alpha(4)beta(1) integrin antagonists and displayed IC50 values in the nanomolar range in cell adhesion inhibition assays and in VCAM-1-induced phosphorylation of extracellular-signal-regulated kinases. Significant activity was observed also toward the homologous integrin alpha(4)beta(7), while they did not display any activity toward selected members of beta 1, beta 2 and beta(3) families. A strong dependence on the stereochemistry of the heterocyclic central core could be observed. The great importance of alpha(4)beta(1), integrin in chronic inflammatory and autoimmune diseases suggests a possible exploitation of these ligands as lead compounds for therapeutic tools development.

  DOI：

  10.1021/acsmedchemlett.5b00125