4-氟-3-(2-呋喃基)丙烯酰苯 | 1565-90-8

• 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: 4-氟-3-(2-呋喃基)丙烯酰苯
• 英文名称: (2E)-1-(4-fluorophenyl)-3-(furan-2-yl)prop-2-en-1-one
• 英文别名: (2E)-3-(2-furanyl)-1-(4-fluorophenyl)propenone；1-(4-Fluorophenyl)-3-(furan-2-yl)prop-2-en-1-one；(E)-1-(4-fluorophenyl)-3-(furan-2-yl)prop-2-en-1-one
• CAS: 1565-90-8
• 化学式: C₁₃H₉FO₂
• mdl: MFCD00020982
• 分子量: 216.212
• InChiKey: BGWADTFLQQUACM-BQYQJAHWSA-N

物化性质

• 熔点：
  68 °C
• 沸点：
  329.8±42.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  4-氟-3-(2-呋喃基)丙烯酰苯 以 乙醇 为溶剂， 反应 10.0h， 生成 2-(3-(4-fluorophenyl)-5-(furan-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-methoxyphenyl)thiazole
  参考文献：
  名称：

  Discovery and modification of sulfur-containing heterocyclic pyrazoline derivatives as potential novel class of β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors

  摘要：

  A series of sulfur-containing heterocyclic pyrazoline derivatives (C1-C18; D1-D9) have been synthesized and purified (all are new except one) to be screened for FabH inhibitory activity. Compound C14 showed the most potent biological activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis (MIC values: 1.56-3.13 mu g/mL), being comparable with the positive control, while D6 performed the best in the thiazolidinone series (MIC values: 3.13-6.25 mu g/mL). They also demonstrated strong broad-spectrum antimicrobial activity. Compounds C14 and D6 exhibited the most potent E. coli FabH inhibitory activity with IC50 of 4.6 and 8.4 mu M, respectively, comparable with the positive control DDCP (IC50 = 2.8 mu M). Docking simulation was performed to position compound C14 and D6 into the E. coli FabH structure active site to determine the probable binding model. The structurally modification of previous compounds and the attempt in innovative target have brought a positive progress. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.05.091
• 作为产物：
  描述：

  1-(4-fluorophenyl)-2-(triphenyl-λ5-arsanylidene)ethanone 以60%的产率得到
  参考文献：
  名称：

  BANSAL R. K.; BHAGCHANDANI G., J. PRAKT. CHEM., 1981, 323, NO 1, 49-54

  摘要：

  DOI：

文献信息

• Synthesis and Anti-Bacterial Activity of Some Heterocyclic Chalcone Derivatives Bearing Thiofuran, Furan, and Quinoline Moieties
  作者：Chang-Ji Zheng、Sheng-Ming Jiang、Zhen-Hua Chen、Bai-Jun Ye、Hu-Ri Piao

  DOI：10.1002/ardp.201100005

  日期：2011.10

  36 Novel heterocyclic chalcone derivatives were synthesized and tested for their anti‐bacterial activity. Some compounds presented good anti‐microbial activities against Gram‐positive bacteria (including the multidrug‐resistant clinical isolates). This class of compounds presented high potency against Streptococcus mutans, among which the derivatives F2 with an MIC of 2 µg/mL was as active as the standard

  合成了 36 种新型杂环查耳酮衍生物并测试了它们的抗菌活性。一些化合物对革兰氏阳性菌（包括耐多药临床分离株）具有良好的抗菌活性。这类化合物对变形链球菌表现出高效能，其中MIC为2 µg/mL的衍生物F2与标准药物（诺氟沙星）活性相同，但活性低于苯唑西林。所有化合物在 64 µg/mL 时均不抑制革兰氏阴性菌（大肠杆菌 CCARM 1924 或大肠杆菌 CCARM 1356）的生长。
• 1,2-Diarylpyrroles as Potent and Selective Inhibitors of Cyclooxygenase-2
  作者：Ish K. Khanna、Richard M. Weier、Yi Yu、Paul W. Collins、Julie M. Miyashiro、Carol M. Koboldt、Amy W. Veenhuizen、Jerry L. Currie、Karen Seibert、Peter C. Isakson

  DOI：10.1021/jm970036a

  日期：1997.5.1

  substituents in the pyrrole ring. Diarylpyrrole 1 is a very potent (COX-2, IC50 = 60 nm) and selective (COX-1/COX-2 = > 1700) inhibitor whereas the isomeric 2 is completely inactive against COX-2. Modifications of the substituents on the fluorophenyl ring in 1 yields very potent inhibitors of COX-2 (IC50 = 40-80 nm) with excellent selectivity (1200 to > 2500) vs COX-1. Analog 20 containing a sulfonamide

  已经合成了一系列的1,2-二芳基吡咯，并发现它们含有非常有效的人环氧化酶-2（COX-2）酶抑制剂。本文介绍了利用Paal-Knorr反应合成靶分子的简短实用方法。1上的亲电子取代以区域选择性方式进行，该方法用于生成许多四取代的吡咯。通过修饰芳基环和吡咯环中的取代基，研究了该系列的详细比吸收率。二芳基吡咯1是非常有效的（COX-2，IC50 = 60 nm）和选择性（COX-1 / COX-2 => 1700）抑制剂，而异构体2对COX-2则完全无活性。对氟苯环上的取代基进行1的修饰可产生非常有效的COX-2抑制剂（IC50 = 40-80 nm），且具有出色的选择性（1200至> 2500）与COX-1。含有磺酰胺基的类似物20是出色的COX-2抑制剂，IC50为14 nm。在吡咯环的3位上含有COCF3，SO2CF3或CH2OAr等基团的四取代吡咯可提供出色的抑制剂（COX-2，IC50
• ANTI-INVASIVE COMPOUNDS
  申请人：Universiteit Gent

  公开号：US20150011620A1

  公开（公告）日：2015-01-08

  The present invention relates to the field of anti-invasive compounds and methods for predicting the anti-invasive activity of said compounds, as well as their use in the prevention and/or treatment of diseases associated with undesired cell invasion; in particular, this invention relates to the field of anti-invasive chalcone-like compounds.

  本发明涉及抗侵袭化合物领域，以及预测该类化合物抗侵袭活性的方法，以及它们在预防和/或治疗与不受欢迎的细胞侵袭相关的疾病中的用途；特别是，本发明涉及抗侵袭的类似香豆素化合物领域。
• Selected furanochalcones as inhibitors of monoamine oxidase
  作者：Sarel J. Robinson、Jacobus P. Petzer、Anél Petzer、Jacobus J. Bergh、Anna C.U. Lourens

  DOI：10.1016/j.bmcl.2013.06.050

  日期：2013.9

  The validity of the chalcone scaffold for the design of inhibitors of monoamine oxidase has previously been illustrated. In a systematic attempt to investigate the effect of heterocyclic substitution on the monoamine oxidase inhibitory properties of this versatile scaffold, a series of furanochalcones were synthesized. The results demonstrate that these furan substituted phenylpropenones exhibited

  查尔酮支架在设计单胺氧化酶抑制剂中的有效性已在前面进行了说明。为了系统地研究杂环取代对这种多功能支架的单胺氧化酶抑制特性的影响，合成了一系列呋喃并呋喃酮。结果表明，这些呋喃取代的苯基丙烯酮对MAO-B表现出中等至良好的抑制活性，但对MAO-A酶的抑制作用弱或没有抑制作用。活性最高的化合物2 E -3-（5-氯呋喃-2-基）-1-（3-氯苯基）丙-2-烯-1-酮的IC 50为抑制MAO-B的值为0.174μM，抑制MAO-A的值为28.6μM。有趣的是，与先前报道的有关查耳酮的数据相反，这些呋喃取代的衍生物起着可逆抑制剂的作用，而动力学分析显示了一种竞争性的结合方式。
• Synthesis, biological activities, and docking study of novel chalcone‐pleuromutilin derivatives
  作者：Chuan Xie、Siyu Zhang、Wei Zhang、Chunxia Wu、Can Yong、Yuhao Sun、Zhengxing Zeng、Qian Zhang、Zixin Huang、Tian Chen、Yuanyuan Zhang

  DOI：10.1111/cbdd.13692

  日期：2020.8

  discover novel antibiotics. The diterpene natural pleuromutilin is a prominent candidate for its special mode of action by inhibiting protein synthesis. In this study, a series of novel pleuromutilin derivatives with chalcone moiety was designed and synthesized, and their antibacterial activities were assessed in vitro. As suggested from the results, most of compounds exhibited potent activities against

  这些天，抗生素抗性问题变得越来越严重，解决该问题的可行解决方案是开发和发现新型抗生素。二萜天然截短侧耳素因其通过抑制蛋白质合成的特殊作用方式而成为重要候选者。在这项研究中，设计和合成了一系列具有查耳酮部分的截短侧耳素新衍生物，并在体外评估了它们的抗菌活性。结果表明，大多数化合物对两种耐甲氧西林的金黄色葡萄球菌均具有有效的活性。（MRSA）ATCC 33591和43300。随后对查尔酮结构，氮杂环衍生物进行了进一步修饰，然后进行了评估，并报道了其对测试菌株的有效活性。进行了初步的对接研究，以探索目标分子与结合位点之间的相互作用。