5-(3-chloro-4-fluorophenyl)furan-2-carbaldehyde | 310459-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(3-chloro-4-fluorophenyl)furan-2-carbaldehyde
• CAS: 310459-43-9
• 化学式: C₁₁H₆ClFO₂
• mdl: MFCD00658941
• 分子量: 224.619
• InChiKey: IKGCOVURJWXEST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 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

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  5-(3-chloro-4-fluorophenyl)furan-2-carbaldehyde 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, antimicrobial and antioxidant activities of 2-[1-{3,5-diaryl-4,5-dihydro-1H-pyrazolenyl}]-4-(4-nitrophenyl)-[1,3]-thiazoles

  摘要：

  In this study, various substituted chalcones, prepared by condensing substituted acetophenones with substituted aldehydes/arylfurfurals, were treated with thiosemicarbazide in basic media to produce 1-thiocarbonyl-3,5-disubstituted pyrazolines which on further reaction with substituted phenacyl bromides afforded the title compounds in good yield. Structures of the newly synthesized compounds were assigned on the basis of elemental analyses, IR, H-1 NMR, and mass spectral studies. The newly synthesized compounds were tested for their in vitro antibacterial and antifungal activities against a variety of microorganisms and antioxidant activities by diphenylpicrylhydrazyl radical scavenging assay. Among the derivatives, compounds 3b, 3e, 6a, and 6h were identified as potent antioxidants. Compounds 3d, 3e, and 6a-f have emerged as the most promising antimicrobial agents displaying the maximum activity against all the tested microorganisms.

  DOI：

  10.1007/s00044-012-0154-3
• 作为产物：
  描述：

  3-氯-4-氟苯胺 在 盐酸 、 copper dichloride 、 sodium nitrite 作用下， 以 水 、 丙酮 为溶剂， 反应 13.0h， 生成 5-(3-chloro-4-fluorophenyl)furan-2-carbaldehyde
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of furan derivatives bearing a rhodanine moiety

  摘要：

  Two series of furan derivatives bearing a rhodanine moiety (4a-l and 5a-l) have been synthesized, characterized, and evaluated for their antibacterial activity. The majority of these compounds showed potent levels of inhibitory activity against a variety of different Gram-positive bacteria, including multidrug-resistant clinical isolates, with minimum inhibitory concentration (MIC) values in the range of 2-16 mu g/mL. In particular, compound 4l was found to be the most potent of the synthesized compounds against the multidrug-resistant strains, with a MIC value of 2 or 4 mu g/mL. None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 mu g/mL. An examination of the cytotoxicities of these agents revealed that they displayed low levels of toxicity toward HeLa cells. All of the compounds synthesized in the current paper were characterized by H-1 and C-13 NMR, infrared, and mass spectroscopy.

  DOI：

  10.1007/s00044-013-0648-7

文献信息

• 5-Aryl-furan derivatives bearing a phenylalanine- or isoleucine-derived rhodanine moiety as potential PTP1B inhibitors
  作者：Tianwei Niu、Peipei Wang、Cheng Li、Tong Dou、Huri Piao、Jia Li、Liangpeng Sun

  DOI：10.1016/j.bioorg.2020.104483

  日期：2021.1

  Two series of 5-aryl-furan derivatives bearing a phenylalanine- or isoleucine-derived rhodanine moiety were identified as competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors. Among the compounds studied, 5g was found to have the best PTP1B inhibitory potency (IC50 = 2.66 ± 0.16 µM) and the best cell division cycle 25 homolog B (CDC25B) inhibitory potency (IC50 = 0.25 ± 0.02 µM). Enzymatic

  两个系列带有苯丙氨酸或异亮氨酸衍生的罗丹宁部分的 5-芳基-呋喃衍生物被鉴定为竞争性蛋白酪氨酸磷酸酶 1B (PTP1B) 抑制剂。在研究的化合物中，发现5g具有最佳的 PTP1B 抑制效力（IC 50 = 2.66 ± 0.16 µM）和最佳的细胞分裂周期 25 同源物 B (CDC25B) 抑制效力（IC 50 = 0.25 ± 0.02 µM）。酶学数据和分子建模结果表明，在羧基的 2-位引入仲丁基显着提高了 PTP1B 抑制活性。
• Novel inhibitors of Plasmodium falciparum based on 2,5-disubstituted furans
  作者：Susann H. Krake、Pablo David G. Martinez、Jenna McLaren、Eileen Ryan、Gong Chen、Karen White、Susan A. Charman、Simon Campbell、Paul Willis、Luiz Carlos Dias

  DOI：10.1016/j.ejmech.2016.12.024

  日期：2017.1

  mice, although the compound later showed poor metabolic stability in liver microsomes through ring- and side chain-oxidation and N-dealkylation. We describe here the synthesis of derivatives of 1, exploring the influence of substitution patterns around the aromatic ring, variations on the alkyl chain and modifications in the core heterocycle, in order to probe potency and metabolic stability, where 4k

  具有血液疟疾测定法的表型HTS运动已被用于发现与现有药物相比具有潜在替代作用机制的新型疟疾治疗化学型。N 1-（5-（3-氯-4-氟苯基）呋喃-2-基）-N 3，N 3-二甲基丙烷-1,3-二胺1被确定为恶性疟原虫NF54（IC 50  = 875 nM），高剂量口服给小鼠后，血浆半衰期很长，尽管该化合物后来在肝微粒体中通过环和侧链氧化和N代谢表现出较差的代谢稳定性-脱烷基。我们在这里描述1的衍生物的合成，探索芳香环周围的取代方式，烷基链上的变异以及核心杂环中的修饰的影响，以探究效能和代谢稳定性，其中4k显示长的半衰期在大鼠中。
• Development of Novel Alkene Oxindole Derivatives As Orally Efficacious AMP-Activated Protein Kinase Activators
  作者：Li-Fang Yu、Yuan-Yuan Li、Ming-Bo Su、Mei Zhang、Wei Zhang、Li-Na Zhang、Tao Pang、Run-Tao Zhang、Bing Liu、Jing-Ya Li、Jia Li、Fa-Jun Nan

  DOI：10.1021/ml400028q

  日期：2013.5.9

  autoinhibition in alpha subunits. In order to enhance its potency at AMPK and bioavailability, structure-activity relationship studies have been performed and resulted in a novel series of AMPK activators based on an alkene oxindole scaffold. Following their evaluation in pharmacological AMPK activation assays, lead compound 24 was identified to possess improved potency as well as favorable pharmacokinetic

  腺苷5'-单磷酸激活蛋白激酶（AMPK）由于其在葡萄糖和脂质代谢中的调节功能而成为有希望的药物靶标。化合物PT1（5）最初是通过对抗α亚基中的自抑制作用，从高通量筛选中鉴定为AMPK的小分子激活剂。为了增强其在AMPK上的效力和生物利用度，已经进行了结构-活性关系研究，并产生了一系列基于烯烃氧吲哚支架的新型AMPK活化剂。在药理AMPK激活分析中对其进行评估后，鉴定出铅化合物24具有更高的效价以及良好的药代动力学特征。在饮食诱发的肥胖（DIO）小鼠模型中，发现化合物24改善了葡萄糖耐量并减轻了胰岛素抵抗。这些烯烃氧吲哚的体外和体内数据值得进一步研究其在代谢相关疾病中的潜在治疗药物。
• Synthesis, Characterization and Biological Studies of Some Bioactive Thiazolotriazole Derivatives
  作者：Manjunatha Kumsi、Boja Poojary、Prajwal Lourdes Lobo、Nalilu Suchetha Kumari、Anoop Chullikana

  DOI：10.1515/znb-2010-1215

  日期：2010.12.1

  anhydrous sodium acetate afforded substituted thiazolo[3,2-b][1,2,4]triazole derivatives 4 and 5. The structures of the newly synthesized compounds were elucidated by elemental analyses and spectral data. The compounds were tested for their in-vitro antimicrobial activities. Graphical Abstract Synthesis, Characterization and Biological Studies of Some Bioactive Thiazolotriazole Derivatives

  从布洛芬 (1) 中以良好的收率合成了关键前体 rac-2-(4-异丁基苯基) 乙基-1,2,4-三唑-5-硫酮 (3)。在乙酸酐和无水乙酸钠存在下，3与5-芳基-呋喃-2-甲醛/取代芳香醛和一氯乙酸在乙酸中的一锅三组分反应得到取代的噻唑并[3,2-b][ 1,2,4]三唑衍生物4和5。通过元素分析和光谱数据阐明了新合成化合物的结构。测试了这些化合物的体外抗微生物活性。一些生物活性噻唑并三唑衍生物的图形摘要合成、表征和生物学研究
• Three-Component Reaction: Synthesis, Characterization, and Biological Study of Some Fused Bridgehead Nitrogen Heterocyclic Systems Containing 4-Methylthiophenyl Moiety
  作者：K. Manjunatha、Boja Poojary、Prajwal L. Lobo、N. Suchetha Kumari、C. Anoop

  DOI：10.1080/10426507.2010.506454

  日期：2011.2.28

  thiazolo-[3,2-b]-1,2,4-triazole derivatives 4 were synthesized by a one-pot, three-component reaction of 3-(4-methylthiobenzyl)-1,2,4-triazole-5-thiol 3, substituted 5-aryl-furan-2-carboxaldehydes/substituted aromatic aldehydes, and monochloroacetic acid in acetic acid using acetic anhydride and anhydrous sodium acetate. Compound 3 was obtained from 4-methylthiophenyl acetic acid by esterification followed

  摘要 通过3-(4-甲硫基苄基)-1,2,4-三唑一锅三组分反应合成了几种取代的噻唑并-[3,2-b]-1,2,4-三唑衍生物4。 -5-硫醇 3、取代的 5-芳基-呋喃-2-甲醛/取代的芳香醛和一氯乙酸在乙酸中使用乙酸酐和无水乙酸钠。化合物 3 由 4-甲硫基苯乙酸通过酯化和肼解获得。通过元素分析和光谱数据阐明了新合成化合物的所有结构。还筛选了新合成的化合物的抗菌和抗炎活性。补充材料可用于本文。转至出版商的在线版磷、硫、和硅和相关元素查看免费的补充文件。图形概要