3-fluoro-4-methoxycinnamic acid | 147906-08-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-fluoro-4-methoxycinnamic acid
• 英文别名: (E)-3-(3-fluoro-4-methoxyphenyl)acrylic acid；3-fluoro-4-methoxy-trans-cinnamic acid；3-Fluor-4-methoxy-trans-zimtsaeure；(E)-3-(3-fluoro-4-methoxyphenyl)-2-propenoic acid；trans 3-(3-fluoro-4-methoxyphenyl)-2-propenoic acid；(E)-3-(3-fluoro-4-methoxyphenyl)prop-2-enoic acid
• CAS: 147906-08-9
• 化学式: C₁₀H₉FO₃
• 分子量: 196.178
• InChiKey: VKZYEBQHWQTZKA-HWKANZROSA-N

物化性质

• 沸点：
  346.4±27.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-fluoro-4-methoxycinnamic acid 在 盐酸 、 diethylzinc 、 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 [2-(3-fluoro-4-methoxyphenyl)cyclopropyl]acetaldehyde
  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-氟-4-甲氧基苄基溴 在 乙酸铵 、 乙醇 、 氯仿 、 乌洛托品 作用下， 生成 3-fluoro-4-methoxycinnamic acid
  参考文献：
  名称：

  Mamaew, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 1290,1293; engl. Ausg. S. 1376, 1378

  摘要：

  DOI：

文献信息

• Design, synthesis and biological evaluation of (E)-5-styryl-1,2,4-oxadiazoles as anti-tubercular agents
  作者：Abhay Atmaram Upare、Pradip K. Gadekar、H. Sivaramakrishnan、Nishigandha Naik、Vijay M. Khedkar、Dhiman Sarkar、Amit Choudhari、S. Mohana Roopan

  DOI：10.1016/j.bioorg.2019.01.054

  日期：2019.5

  Cinnamic acid and its derivatives are known for anti-tubercular activity. The present study reports the synthesis of cinnamic acid derivatives via bioisosteric replacement of terminal carboxylic acid with "oxadiazole". A series of cinnamic acid derivatives (styryl oxadiazoles) were designed and synthesized in good yields by reaction of substituted cinnamic acids (2, 15a-15s) with amidoximes. The synthesized

  肉桂酸及其衍生物具有抗结核活性。本研究报道了通过用“恶二唑”对末端羧酸进行生物等位取代来合成肉桂酸衍生物。通过取代肉桂酸（2，15a-15s）与a肟的反应，设计并合成了一系列肉桂酸衍生物（苯乙烯基恶二唑），并以高收率合成。体外评估了合成的苯乙烯基恶二唑类药物对结核分枝杆菌（Mtb）H37Ra菌株的抗结核活性。结构-活性关系（SAR）研究确定了几种具有混合抗结核特性的化合物。化合物32显示出有效的抗结核活性（IC50 = 0.045 µg / mL）。
• Therapeutic agent for Parkinson's disease
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US05484920A1

  公开（公告）日：1996-01-16

  Agents for the treatment of Parkinson's disease contain, as an active ingredient, a xanthine derivative or a pharmaceutically acceptable salt thereof. The xanthine derivative is represented by the formula: ##STR1## in which R.sup.1, R.sup.2 are R.sup.3 are independently hydrogen, lower alkyl, lower alkenyl, or lower alkynyl; and R.sup.4 represents cycloalkyl, --(CH.sub.2).sub.n --R.sup.5 (in which R.sup.5 represents substituted or unsubstituted aryl or a substituted or unsubstituted heterocyclic group; and n is an integer of 0 to 4), or ##STR2## in which Y.sup.1 and Y.sup.2 represent independently hydrogen, halogen, or lower alkyl; and Z represents substituted or unsubstituted aryl, ##STR3## in which R.sup.6 represents hydrogen, hydroxy, lower alkyl, lower alkoxy, halogen, nitro, or amino; and m represents an integer of 1 to 4, or a substituted or unsubstituted heterocyclic group; and X.sup.1 and X.sup.2 represent independently O or S.

  治疗帕金森病的药剂，其活性成分是一种黄嘌呤衍生物或其药物可接受的盐。该黄嘌呤衍生物的化学公式如下：##STR1## 其中，R.sup.1、R.sup.2和R.sup.3独立地代表氢、低级烷基、低级烯基或低级炔基；R.sup.4代表环烷基、--(CH.sub.2).sub.n --R.sup.5（其中R.sup.5代表取代或未取代的芳基或取代或未取代的杂环族；n是0到4之间的整数），或##STR2## 其中，Y.sup.1和Y.sup.2独立地代表氢、卤素或低级烷基；Z代表取代或未取代的芳基，##STR3## 其中，R.sup.6代表氢、羟基、低级烷基、低级烷氧基、卤素、硝基或氨基；m代表1到4之间的整数，或取代或未取代的杂环族；X.sup.1和X.sup.2独立地代表氧或硫。
• [EN] GPR120 RECEPTOR AGONISTS AND USES THEREOF<br/>[FR] AGONISTES DU RÉCEPTEUR GPR120 ET LEURS UTILISATIONS
  申请人：METABOLEX INC

  公开号：WO2011159297A1

  公开（公告）日：2011-12-22

  GPR120 agonists are provided. These compounds are useful for the treatment of metabolic diseases, including Type II diabetes and diseases associated with poor glycemic control.

  GPR120激动剂已提供。这些化合物对于治疗代谢性疾病，包括II型糖尿病和与血糖控制不佳有关的疾病非常有用。
• [EN] GPR120 RECEPTOR AGONISTS AND USES THEREOF<br/>[FR] AGONISTES DE RÉCEPTEURS GPR 120 ET LEURS APPLICATIONS
  申请人：METABOLEX INC

  公开号：WO2010080537A1

  公开（公告）日：2010-07-15

  GPR120 agonists are provided. These compounds are useful for the treatment of metabolic diseases, including Type II diabetes and diseases associated with poor glycemic control.

  GPR120激动剂已提供。这些化合物对于治疗代谢性疾病，包括II型糖尿病和与血糖控制不佳有关的疾病非常有用。
• Compound and use of the same as medicine
  申请人：Tsumura & Co.

  公开号：US05344845A1

  公开（公告）日：1994-09-06

  Disclosed herein is a specific cinnamic acid derivative such as methyl 4-(4-acetoxy-3-methoxycinnamanide)-1-cyclohexanecarboxylate, or a pharmaceutically acceptable salt thereof. These compounds are useful as IV-type allergic reaction-suppressive drugs.

  本文披露了一种特定的肉桂酸衍生物，例如甲基4-(4-乙酰氧基-3-甲氧基肉桂酰胺基)-1-环己烷羧酸酯，或其药用可接受的盐。这些化合物可用作IV型过敏反应抑制药物。