ethyl 3-(3-pyridyl)-4-(p-hydroxyphenyl)butyrate | 329978-35-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-(3-pyridyl)-4-(p-hydroxyphenyl)butyrate
• 英文别名: ethyl ()-4-(4-hydroxyphenyl)-3-(pyridin-3-yl)butanoate；Ethyl (+/-)-4-(4-hydroxyphenyl)-3-(pyridin-3-yl)butanoate；ethyl 4-(4-hydroxyphenyl)-3-pyridin-3-ylbutanoate
• CAS: 329978-35-0
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: XEEOFIWOHPOVNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-(3-pyridyl)-4-(p-hydroxyphenyl)butyrate 在 palladium on activated charcoal sodium hydroxide 、 乙醇 、 三苯基膦 、 环己烯 、 偶氮二甲酸二乙酯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 4-[3-(2-N-pyridyl)amino]-1-propyloxyphenyl-3-(3-pyridyl)butyric 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：

  烟酸甲酯 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 氢溴酸 、 氢气 、 sodium methylate 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 85.5h， 生成 ethyl 3-(3-pyridyl)-4-(p-hydroxyphenyl)butyrate
  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

• Vitronectin receptor antagonists
  申请人：Manley Peter J.

  公开号：US06881736B1

  公开（公告）日：2005-04-19

  Compounds of the formula (I) are disclosed which are vitronectin receptor antagonists and are useful in the treatment of osteoporosis: wherein R 1 is Het or Ar R 2 is or a pharmaceutically acceptable salt thereof.

  公开了化合物（I）的公式，它们是纤维连接蛋白受体拮抗剂，可用于治疗骨质疏松症：其中R1为Het或Ar，R2为其药学上可接受的盐。
• VITRONECTIN RECEPTOR ANTAGONISTS
  申请人：SmithKline Beecham Corporation

  公开号：EP1218005B1

  公开（公告）日：2004-12-15
• EP1218005A4
  申请人：——

  公开号：EP1218005A4

  公开（公告）日：2002-10-09
• US6881736B1
  申请人：——

  公开号：US6881736B1

  公开（公告）日：2005-04-19
• [EN] VITRONECTIN RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR DE LA VITRONECTINE
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2001017959A2

  公开（公告）日：2001-03-15

  Compounds of formula (I) are disclosed which are vitronectin receptor antagonists and are useful in the treatment of osteoporosis wherein R1 is Het- or Ar; R2 is formula (a) or formula (b); or a pharmaceutically acceptable salt thereof.