[2-(3-methoxyphenyl)cyclopropyl]acetic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [2-(3-methoxyphenyl)cyclopropyl]acetic acid
• 英文别名: 2-[2-(3-Methoxyphenyl)cyclopropyl]acetic acid
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: RJKPDWZDSDRHTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [2-(3-methoxyphenyl)cyclopropyl]acetic acid 在 盐酸 、 三溴化硼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 ethyl (2-{3-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]phenyl}cyclopropyl)acetate
  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：

  3-Methoxycinnamic acid 在 sodium hydroxide 、 sodium hydride 、 二异丁基氢化铝 、 silver nitrate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 1-羟基苯并三唑一水物 、 三乙胺 作用下， 生成 [2-(3-methoxyphenyl)cyclopropyl]acetic 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

文献信息

• Cycloalkyl alkanoic acids as integrin receptor antagonists derivatives
  申请人：——

  公开号：US20040092538A1

  公开（公告）日：2004-05-13

  The present invention relates to a class of compounds represented by the Formula I 1 or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the &agr; v &bgr; 3 and/or &agr; v &bgr; 5 integrin.

  本发明涉及一类由公式I代表的化合物 1 或其药用可接受的盐，包含公式I化合物的药物组合物，以及选择性地抑制或拮抗α v β 3 和/或α v β 5 整合素的方法。
• STABILIZED BODY CARE PRODUCTS, HOUSEHOLD PRODUCTS, TEXTILES AND FABRICS
  申请人：Ciba Specialty Chemicals Holding Inc.

  公开号：EP1499286A1

  公开（公告）日：2005-01-26
• US6921767B2
  申请人：——

  公开号：US6921767B2

  公开（公告）日：2005-07-26
• [EN] STABILIZED BODY CARE PRODUCTS, HOUSEHOLD PRODUCTS, TEXTILES AND FABRICS<br/>[FR] PRODUITS POUR SOINS CORPORELS STABILISES, PRODUITS MENAGERS, TEXTILES ET TISSUS
  申请人：CIBA SC HOLDING AG

  公开号：WO2003103622A1

  公开（公告）日：2003-12-18

  Disclosed are stabilized body care products, household products, textiles and fabrics which comprise certain hindered nitroxyl, hydroxylamine and hydroxylamine salt compounds. Dyed products and articles are effectively stabilized against color degradation. The products are for example skin-care products, hair-care products, dentifrices, cosmetics, laundry detergents and fabric softeners, non-detergent based fabric care products, household cleaners and textile-care products.
• 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
  作者：Srinivasan R. Nagarajan、Hwang-Fun Lu、Alan F. Gasiecki、Ish K. Khanna、Mihir D. Parikh、Bipinchandra N. Desai、Thomas E. Rogers、Michael Clare、Barbara B. Chen、Mark A. Russell、Jeffery L. Keene、Tiffany Duffin、V. Wayne Engleman、Mary B. Finn、Sandra K. Freeman、Jon A. Klover、G. Alan Nickols、Maureen A. Nickols、Kristen E. Shannon、Christina A. Steininger、William F. Westlin、Marisa M. Westlin、Melanie L. Williams

  DOI：10.1016/j.bmc.2007.03.020

  日期：2007.5

  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.