3-(5-nitrofuran-2-yl)-1-phenylprop-2-en-1-one | 4332-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 3-(5-nitrofuran-2-yl)-1-phenylprop-2-en-1-one
• 英文别名: 1-phenyl-3-(5-nitro-2-furyl)-2-propenone；(5-Nitro-2-furfurylidene)acetophenone；3-(5-nitro-furan-2-yl)-1-phenyl-propenone；3-<5-Nitro-<2>furyl>-1-phenyl-prop-2-en-1-on；3-<5-Nitro-<2>furyl>-1-phenyl-propenon；1-Phenyl-3-<5-nitro-furyl-(2)>-propen-(2)-on-(1)；3-(5-Nitro-2-furanyl)-1-phenyl-2-propen-1-one
• CAS: 4332-88-1
• 化学式: C₁₃H₉NO₄
• 分子量: 243.219
• InChiKey: ZLDNVNUDRJJGII-UHFFFAOYSA-N

物化性质

• 熔点：
  137-138 °C
• 沸点：
  393.9±42.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 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：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(5-nitrofuran-2-yl)-1-phenylprop-2-en-1-one 在 溴 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 生成 5-phenyl-1-(2,4-dibromophenyloxyacetyl)-5-hydroxy-3-(5-nitro-2-furyl)pyrazoline
  参考文献：
  名称：

  Holla, B Shivarama; K, Shridhara, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 12, p. 1139 - 1141

  摘要：

  DOI：
• 作为产物：
  描述：

  5-硝基糠醛 、 苯乙酮 在 硫酸 、 溶剂黄146 作用下， 生成 3-(5-nitrofuran-2-yl)-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of 4-(5-nitrofuran-2-yl)prop-2-en-1-one derivatives as potent antitubercular agents

  摘要：

  Based on stereoelectronic feature analysis using density functional theory (DFT) at B3LYP/3-21*G level, a series of 4-(5-nitrofuran-2-yl)prop-2-en-1-one derivatives with low LUMO energies (<-0.10 eV); concentrated over the nitro group, furan moiety and alpha,beta-unsaturated carbonyl bridge were envisaged as potential antitubercular agents. The target compounds were prepared by condensation of 5-nitro-2-furaldehyde with various ketones under acidic condition. The compounds were evaluated for antitubercular activity against Mycobacterium tuberculosis H37Rv and their cytotoxicity in VERO cell line. Several synthesized compounds showed good antitubercular activity of <5 mu M along with low cytotoxicity. In particular, compound ((E)-3-(5-nitrofuran-2-yl)-1-(4-(piperidin-1-yl) phenyl) prop-2-en-1-one) (3v) was found to be very potent (MIC: 0.19 mu M) with good selectivity index (MIC90/CC50: > 1800). Thus, this study shows the potential of stereoelectronic property analysis in developing improved nitroaromatics as antitubercular agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.127

文献信息

• Studies on Heteroaromaticity. LII. Syntheses and Reactions of α-Acetylenic Ketones Containing Nitrofuran Ring
  作者：Tadashi Sasaki、Toshiyuki Yoshioka

  DOI：10.1246/bcsj.44.803

  日期：1971.3

  2-(5-Nitro-2-furyl)-1-phenyl- (IVa), -p-methylphenyl- (IVb) and -(2-furyl)-acetylene (IVc) were prepared by condensation of nitrofurfural with the corresponding aryl methyl ketones, followed by bromination and dehydrobromination. Addition of aniline and cyclohexylamine to IVa afforded simple adducts Va and VIa respectively. Treatment of IVa,b with hydroxylamine, hydrazine hydrate, semicarbazide and

  2-(5-硝基-2-呋喃基)-1-苯基-(IVa)、-p-甲基苯基-(IVb)和-(2-呋喃基)-乙炔(IVc)是通过硝基糠醛与相应的芳基缩合制备的甲基酮，然后进行溴化和脱溴化氢。将苯胺和环己胺加入到 IVa 中分别得到简单的加合物 Va 和 VIa。用羟胺、水合肼、氨基脲和苯甲脒处理 IVa,b 分别得到异恶唑 (VIIIa,b)、吡唑 (VIIIa,b)、1-氨基吡唑 (IXa,b) 和嘧啶 (Xa,b)。在室温下用氧化苄腈处理时，IVa 与呋喃一起提供异恶唑 XIa，但 IVa,b 与 5-硝基-2-呋喃甲腈的热 1,3-偶极反应仅提供异恶唑 XIIa,b。为了比较，在室温下用氧化苄腈处理 5-硝基-2-糠基二苯甲酮 (IIa) 以提供异恶唑啉 XIIIa 和 XIVa 与呋喃的异构混合物。5-硝基-2-糠基丙酮的类似处理...
• Regioselective Synthesis of Nitrofuran Containing Novel Spiropyrrolidine Library through 1,3-Dipolar Cycloaddition Reactions
  作者：Sahana Mallya、Balakrishna Kalluraya、K. S. Girisha

  DOI：10.1002/jhet.2092

  日期：2015.3

  A novel series of nitrofuran containing spiropyrrolidines has been synthesized with high regioselectivity in moderate to excellent yields via 1,3‐dipolar cycloaddition reaction of azomethine ylides with various substituted chalcones.

  通过偶氮甲亚胺与各种取代的查耳酮的1，3-偶极环加成反应，合成了一系列新的含硝基呋喃的螺吡咯烷，具有较高的区域选择性，产率中等至优异。
• Design and synthesis of sulfur cross-linked 1,3,4-oxadiazole-nitro(furan/thiophene)-propenones as dual inhibitors of inflammation and tuberculosis: molecular docking and Hirshfeld surface analysis
  作者：Vishwanath Turukarabettu、Balakrishna Kalluraya、Monika Sharma

  DOI：10.1007/s00706-019-02507-2

  日期：2019.11

  the aim of developing dual inhibitors of multidrug-resistant tuberculosis and inflammation. The in vivo anti-inflammatory activity results showed excellent inhibition of rat paw edema. The methoxybenzene/nitrofuryl derivative of title compounds showed 83% inhibition of inflammation during 2–6 h after carrageenan injection. All compounds showed anti-tuberculosis activity at MIC of 50 µg/cm3. The molecular

  摘要一系列3- [5-硝基（呋喃/噻吩）-2-基] -1-芳基-3-（5-芳基1,3,4-恶二唑-2-基硫基）丙-2-烯-1为了开发耐多药结核病和炎症的双重抑制剂，合成并研究了一种衍生物。体内抗炎活性结果显示对大鼠爪水肿具有极好的抑制作用。角叉菜胶注射后2–6 h，标题化合物的甲氧基苯/硝基呋喃基衍生物显示出83％的炎症抑制作用。所有化合物在MIC为50 µg / cm 3时均显示出抗结核活性。分子对接研究表明，恶二唑和硝基呋喃基团通过与Tyr 385，Ser 530，Tyr 467和Tyr 158氨基形成氢键，在COX1，COX2、5-LOs和InhA酶的抑制位点中起重要作用。酸残基。新化合物是对大肠杆菌具有潜在抑制作用的活性抗菌剂。毒性结果显示人肾细胞系具有良好的存活率，其IC 50值大于100 µg / cm 3浓度。化合物的Hirshfeld表面分析和静电势图显示出良好的分子间接触以及氢键供体和受体的电势。
• Synthetic and theoretical investigation on nano‐Au/TiO₂catalyzed hydrothiolation for construction of C─S bond: Experimental and DFT study
  作者：Vishwanath Turukarabettu、Balakrishna Kalluraya

  DOI：10.1002/poc.4040

  日期：2020.4

  reaction proceeded via regioselective Michael‐type anti‐addition and gave the corresponding sulfur bridged 1,3,4‐oxadiazole‐propenone in excellent yield. The compounds were characterized by analytical and spectral techniques. A gas phase molecular modeling study of nanogold‐catalyzed hydrothiolation of acetylenic ketone with 5‐aryl‐1,3,4‐oxadiazol‐2‐thiol was carried out using density functional theory

  在本文中，我们描述了一种新的合成和理论方法，用于在经历纳米金催化氢硫键化反应的杂环分子中构建C-S键。实验研究表明，该反应是通过区域选择性迈克尔型抗加成反应进行的，并以优异的收率得到了相应的硫桥联的1,3,4-恶二唑-丙烯酮。通过分析和光谱技术对化合物进行表征。使用密度泛函理论（DFT）计算进行了纳米金催化的炔基酮与5-芳基-1,3,4-恶二唑-2-硫醇的氢硫键化的气相分子建模研究。它显示出炔酮在纳米金上的吸附，并在炔基的β碳上具有较好的配位作用。电荷计算表明，在纳米金上吸附时，炔基在性质上变得更具极性。最前沿的最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）分析表明，巯基和炔属β碳之间的分子轨道可能重叠，从而得到Z异构体。进行了键合参数的实验和理论验证。在此基础上，结合理论计算和实验证明，提出了一种可能的加氢硫醇化反应机理。
• Aleksandrova,I.A. et al., Journal of Organic Chemistry USSR (English Translation), 1976, vol. 12, p. 2358 - 2360
  作者：Aleksandrova,I.A. et al.

  DOI：——

  日期：——