1-(3-pyridyl)-2-(p-hydroxyphenyl)ethan-1-one | 940288-59-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-pyridyl)-2-(p-hydroxyphenyl)ethan-1-one
• 英文别名: 2-(4-hydroxy-phenyl)-1-pyridin-3-yl-ethanone；2-(4-Hydroxyphenyl)-1-(pyridin-3-YL)ethanone；2-(4-hydroxyphenyl)-1-pyridin-3-ylethanone
• CAS: 940288-59-5
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: JQDQROIMSMFJRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-pyridyl)-2-(p-hydroxyphenyl)ethan-1-one 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 氢气 、 三苯基膦 、 环己烯 、 偶氮二甲酸二乙酯 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 113.0h， 生成
  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：

  对甲氧基苯乙腈 在 氢溴酸 、 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 20.5h， 生成 1-(3-pyridyl)-2-(p-hydroxyphenyl)ethan-1-one
  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

文献信息

• WO2008/115141
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] 4, 5-DIHYDRO-1,3-THIAZOL-2-AMINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF RESPIRATORY, CARDIOVASCULAR, NEUROLOGICAL OR GASTROINTESTINAL DISORDERS<br/>[FR] DÉRIVÉS DE 4,5-DIHYDRO-1,3-THIAZOL-2-AMINE ET LEUR UTILISATION POUR LE TRAITEMENT DE TROUBLES RESPIRATOIRES, CARDIOVASCULAIRES, NEUROLOGIQUES OU GASTROINTESTINAUX
  申请人：ALBIREO AB

  公开号：WO2008115141A1

  公开（公告）日：2008-09-25

  [EN] The present invention relates to compounds of formula (I), (XI) or (CI), to pharmaceutical compositions containing said compounds and to the use of said compounds in therapy. The present invention further relates to processes for the preparation of compounds of formula (I), (XI) or (CI) and to new intermediates used in the preparation thereof.
  [FR] La présente invention concerne des composés de formule (I), (XI) ou (CI), des compositions pharmaceutiques qui contiennent lesdits composés et l'utilisation desdits composés en thérapie. La présente invention concerne également des procédés de préparation de composés de formule (I), (XI) ou (CI) et de nouveaux intermédiaires utilisés dans la préparation de ces composés.