3-(5-(4-氯苯基)-呋喃-2-基)-丙烯酸 | 62806-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(5-(4-氯苯基)-呋喃-2-基)-丙烯酸
• 英文名称: (E)-3-[5-(4-chlorophenyl)-2-furyl]-2-propenoic acid
• 英文别名: (E)-3-(5-(4-chlorophenyl)furan-2-yl)acrylic acid；3-(5-(4-chlorophenyl)-furan-2-yl)-acrylic acid；3-[5-(4-chloro-phenyl)-furan-2-yl]-acrylic acid；3t-[5-(4-chloro-phenyl)-[2]furyl]-acrylic acid；3t-[5-(4-Chlor-phenyl)-[2]furyl]-acrylsaeure；(2E)-3-[5-(4-chlorophenyl)-2-furyl]acrylic acid；3-[5-(4-Chlorophenyl)furan-2-yl]acrylic acid；(E)-3-[5-(4-chlorophenyl)furan-2-yl]prop-2-enoic acid
• CAS: 62806-34-2
• 化学式: C₁₃H₉ClO₃
• mdl: MFCD00192863
• 分子量: 248.666
• InChiKey: FPSINWFYJYHUBV-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(5-(4-氯苯基)-呋喃-2-基)-丙烯酸 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (E)-3-[5-(4-chlorophenyl)-2-furyl]acrylic acid chloride
  参考文献：
  名称：

  Structure–Activity relationships of novel anti-Malarial agents. Part 4: N-(3-Benzoyl-4-tolylacetylaminophenyl)-3-(5-aryl-2-furyl)acrylic acid amides

  摘要：

  In a previous report, we have described novel anti-malarial compounds based on a 2,5-diaminobenzophenone scaffold. Here, we have invesigated acryloyl derivatives carrying a biaryl structure consisting of a terminal aryl residue and a central 2-furyl ring. Several compounds were obtained in the series of para-substituted phenylfurylacryloyl derivatives that displayed improved anti-malarial activity in comparison to earlier described derivatives. From the structure-activity relationships it can be deduced that there has to be a lipophilic moiety in the para-position of the terminal phenyl residue. Furthermore, there are indications that, alternatively, activity may benefit from the presence of a polar moiety with hydrogen bond acceptor properties. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00555-3
• 作为产物：
  描述：

  rac-2-acetamido-3-[5-(4-chlorophenyl)furan-2-yl]propanoicacid 在 盐酸 、 phenylalanine ammonia-lyase 作用下， 以 1,4-二氧六环 为溶剂， 反应 172.0h， 生成 3-(5-(4-氯苯基)-呋喃-2-基)-丙烯酸
  参考文献：
  名称：

  2-Amino-3-(5-phenylfuran-2-yl)propionic Acids and 5-Phenylfuran-2-ylacrylic Acids are Novel Substrates of Phenylalanine Ammonia-Lyase

  摘要：

  Both racemic 2-amino-3-(5-phenylfuran-2-yl)propionic acids and 5-phenylfuran-2-ylacrylic acids were synthesized and spectroscopically characterized (UV, EI-MS, H-1-NMR and C-13-NMR). The phenyl group of the 5-phenylfuranyl residue carried no (rac-1a) para-Br (rac-1b) or Cl para or ortho (rac-1c, d) substituents. The novel furanylalanines were used as substrates of recombinant phenylalanine ammonia-lyase (PAL). When 50% of the racemic 5-phenylfuranylalanines were converted into the corresponding acrylates, the D-enantiomers of the substrates could be isolated. The L-enantiomers could be prepared from the substituted acrylates when the PAL reaction was reversed in the presence of 6 M ammonia at pH 10.

  DOI：

  10.3987/com-10-s(e)60

文献信息

• Structure–activity relationship of the cinnamamide family of antibiotic potentiators for methicillin-resistant <i>Staphylococcus aureus</i> (MRSA)
  作者：Enrico Speri、Jennifer Fishovitz、Shahriar Mobashery

  DOI：10.1039/c8md00479j

  日期：——

  restored. We describe herein our discovery of one class of such agents, the cinnamamide family of antibiotic potentiators. A hit compound of the class (compound 1) showed modest potentiation of the activity of oxacillin, a penicillin antibiotic, against an MRSA strain. A total of 50 analogues of compound 1 were prepared and screened. Seven of these compounds showed more dramatic potentiation of the antibacterial

  耐甲氧西林金黄色葡萄球菌（MRSA）是全球性的公共卫生威胁。MRSA已进化出一套复杂的生化过程，可动员生物体抵抗β-内酰胺类抗生素的攻击而产生可诱导的抗性。在药理学上干扰这种机制有可能逆转β-内酰胺耐药性表型，从而恢复对过时抗生素的敏感性。我们在本文中描述了我们发现的一类此类药剂，即抗生素增强剂肉桂酰胺家族。此类命中化合物（化合物1）对青霉素类抗生素奥沙西林的抗MRSA菌株活性适度增强。总共50个化合物1的类似物准备和筛选。这些化合物中的七个显示出更显着的抗菌活性增强作用，从而使抗生素的最小抑菌浓度（MIC）降低了64到128倍。
• RETRACTED ARTICLE: Design, synthesis of novel oxazolidino-amides/sulfonamides conjugates and their impact on antibacterial activity
  作者：Yarlagadda Bharath、Gopi Reddy Alugubelli、Reddymasu Sreenivasulu、Mandava. V. Basaveswara Rao

  DOI：10.1007/s11696-017-0298-1

  日期：2018.2

  AbstractIn view of generating new compounds for future drug development, we have synthesized oxazolidinones library of aryl amides and aryl sulfonamide derivatives. These compounds were screened in vitro against panel of susceptible and resistant Gram-positive (Staphylococcus aureus and Bacillus subtilis), Gram-negative bacteria (Pseudomonas aeruginosa), fungi (Candida albicans) strains, and Mycobacterium

  摘要考虑到产生用于未来药物开发的新化合物，我们已经合成了芳基酰胺和芳基磺酰胺衍生物的恶唑烷酮文库。这些化合物在体外针对敏感和耐药的革兰氏阳性菌（金黄色葡萄球菌和枯草芽孢杆菌），革兰氏阴性菌（铜绿假单胞菌），真菌（白色念珠菌）和结核分枝杆菌（Mtb）进行了筛选。其中，对10d和11a化合物已针对12种真菌菌株进行了评估，并显示出显着的抗真菌活性，其效力比氟康唑高约37倍。 图形概要
• Synthesis of 2-Arylfuro[3,2-c]pyridines and Their Derivatives
  作者：Alžbeta Krutošíková、Róbert Sleziak

  DOI：10.1135/cccc19961627

  日期：——

  A series of 2-arylfuro[3,2-c]pyridines was synthesized. 3-(5-Aryl-2-furyl)propenoic acids 1a-1h were converted to the acid azides 2a-2h, which in turn were cyclized to give 2-arylfuro[3,2-c]pyridine-4(5H)-ones 4a-4h by heating in Dowtherm. The pyridones 4a-4f were aromatized with phosphorus oxychloride to the 2-aryl-4-chlorofuro[3,2-c]pyridines 5a-5f, which were reduced with zinc and acetic acid to the title compounds 6a-6f. Reacted with phosphorus(V) sulfide, the pyridones 4a-4f yielded the corresponding thiones 7a-7f.

  合成了一系列2-芳基呋喃[3,2-c]吡啶化合物。3-(5-芳基-2-呋喃基)丙烯酸1a-1h被转化为酸叠氮化物2a-2h，然后经过环化反应在Dowtherm中加热得到2-芳基呋喃[3,2-c]吡啶-4(5H)-酮4a-4h。吡啶酮4a-4f经过磷氯氧化物芳构化为2-芳基-4-氯呋喃[3,2-c]吡啶5a-5f，再用锌和乙酸还原为目标化合物6a-6f。与五氧化二磷反应，吡啶酮4a-4f生成相应的硫醚7a-7f。
• Novel linezolid-based oxazolidinones as potent anticandidiasis and antitubercular agents
  作者：Shaik Faazil、M. Shaheer Malik、Saleh A. Ahmed、Reem I. Alsantali、Poornachandra Yedla、Meshari A. Alsharif、Iqbal N. Shaikh、Ahmed Kamal

  DOI：10.1016/j.bioorg.2022.105869

  日期：2022.9

  Oxazolidinones are well-known antibacterial agents, with few investigations reported to exploit their antifungal properties. Herein, we report the design and synthesis of a series of linezolid-based oxazolidinones as potent anticandidiasis and antitubercular agents. Studies revealed that two of the novel oxazolidinones 2 and 3a exhibited excellent anticandidiasis activity against different Candida fungus

  由于病态的共同发病机制和免疫功能低下患者的增加，对新的抗真菌和抗结核药物的探索是当务之急。前进的方法之一是探索和重新利用已建立的药效团以用于所需的应用。恶唑烷酮是众所周知的抗菌剂，很少有研究报道利用它们的抗真菌特性。在此，我们报告了一系列基于利奈唑胺的恶唑烷酮类药物作为有效的抗念珠菌病和抗结核药物的设计和合成。研究表明，两种新型恶唑烷酮2和3a对不同的念珠菌表现出优异的抗念珠菌病活性真菌菌株，优于标准药物。机理和对接研究表明，恶唑烷酮类是麦角甾醇生物合成途径的更好抑制剂，比所使用的对照组更好。此外，恶唑烷酮2和3a对M. tuberculosis H 37 Rv也表现出显着的抑制活性，MIC 值分别为 1 和 2 μg/ml。计算研究证明了化合物与转录调节阻遏蛋白的结合，分子动力学模拟加强了这一点。药效团建模实验验证了两种靶蛋白的分子对接结果。
• AGENT FOR CONTROLLING FUNCTION OF GPR34 RECEPTOR
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1849465A1

  公开（公告）日：2007-10-31

  The present invention provides a GPR receptor function regulator comprising the compound represented by the formula: [wherein ring A is an optionally substituted isocyclic or heterocyclic ring, P is a bond or spacer, ring D is an optionally substituted monocyclic aromatic ring which may be condensed with a 5-to 7-membered ring, V is a bond or the group represented by the formula -CR14=CR15 - or - N=CR16- (wherein R14, R15 and R16 each represents a hydrogen atom or optionally substituted hydrocarbon group), Q is a bond or spacer, and W is a carboxyl or a group biologically equivalent to a carboxyl] or its salt or a prodrug thereof

  本发明提供了一种 GPR 受体功能调节剂，包括由式表示的化合物： [其中环A是任选取代的异环或杂环，P是键或间隔物，环D是任选取代的单环芳香环，可与5-7元环缩合，V是键或由式-CR14＝CR15-或-N＝CR16-代表的基团（其中R14、R15 和 R16 各代表一个氢原子或任选取代的烃基），Q 是键或间隔物，W 是羧基或生物等价于羧基的基团]或其盐或其原药