ethyl (+/-)-3-methyl-4-[4-[3-(1-oxopyridin-2-yl)amino-1-propyloxy]phenyl]butanoate | 243641-88-5

• 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: ethyl (+/-)-3-methyl-4-[4-[3-(1-oxopyridin-2-yl)amino-1-propyloxy]phenyl]butanoate
• CAS: 243641-88-5
• 化学式: C₂₁H₂₈N₂O₄
• 分子量: 372.464
• InChiKey: CCRSJHPWWYISIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  27.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  74.5
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl (+/-)-3-methyl-4-[4-[3-(1-oxopyridin-2-yl)amino-1-propyloxy]phenyl]butanoate 在 palladium on activated charcoal sodium hydroxide 、 乙醇 、 环己烯 作用下， 以 乙醇 为溶剂， 生成 (+/-)3-methyl-4-[4-[3-(pyridin-2-yl)amino-1-propyloxy]phenyl]butanoic acid
  参考文献：
  名称：

  Discovery of +(2-{4-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]phenyl}-cyclopropyl)acetic acid as potent and selective αvβ3 inhibitor: Design, synthesis, and optimization

  摘要：

  The integrin alpha(v)beta(3) is expressed in a number of cell types and is thought to play a major role in several pathological conditions. Various small molecules that inhibit the integrin have been shown to suppress tumor growth and retinal angiogenesis. The tripeptide Arg-Gly-Asp (RGD), a common binding motif in several ligands that bind to alpha(v)beta(3), has been depeptidized and optimized in our efforts toward discovering a small molecule inhibitor. We recently disclosed the synthesis and biological activity of several small molecules that did not contain any peptide bond and mimic the tripeptide RGD. The phenethyl group in one of the lead compounds was successfully replaced with a cyclopropyl moiety. The new lead compound was optimized for potency, selectivity, and for its ADME properties. We describe herein the discovery, synthesis, and optimization of cyclopropyl containing analogs that are potent and selective inhibitors of alpha(v)beta(3). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.020
• 作为产物：
  描述：

  ethyl (+/-)-4-(4-hydroxyphenyl)-3-methylbutanoate 、 2-[(3-hydroxy-1-propyl)amino]pyridine-N-oxide 在 diisopropyl (E)-azodicarboxylate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以54%的产率得到ethyl (+/-)-3-methyl-4-[4-[3-(1-oxopyridin-2-yl)amino-1-propyloxy]phenyl]butanoate
  参考文献：
  名称：

  Vitronectin Receptor Antagonists

  摘要：

  公式（1）的化合物被披露为抗血浆粘附素受体的拮抗剂，并且在骨质疏松症的治疗中有用：1

  公开号：

  US20020147334A1