4-<3-(2-Hydroxy-phenyl)-3-oxo-propen-(1)-yl>-benzonitril | 3033-94-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-<3-(2-Hydroxy-phenyl)-3-oxo-propen-(1)-yl>-benzonitril
• 英文别名: 4-Cyan-2'-hydroxy-chalkon；4-[3-(2-Hydroxy-phenyl)-3-oxo-propen-(1)-yl]-benzonitril；4-[3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]benzonitrile
• CAS: 3033-94-1
• 化学式: C₁₆H₁₁NO₂
• 分子量: 249.269
• InChiKey: NLXKPBYOVGGPRF-UHFFFAOYSA-N

物化性质

• 熔点：
  143-145 °C
• 沸点：
  474.0±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 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：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-<3-(2-Hydroxy-phenyl)-3-oxo-propen-(1)-yl>-benzonitril 在 吡啶 、 mercury(II) diacetate 作用下， 反应 1.0h， 以75%的产率得到4-((3-oxobenzofuran-2(3H)-ylidene)methyl)benzonitrile
  参考文献：
  名称：

  Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives

  摘要：

  A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives (aurones, 1-20) were synthesized and screened for their inhibitory activity against hMAO. Seventeen compounds (1-5, 7-17, 19) were found to be selective towards hMAO-B, while two were non -selective (6 and 20) and one (18) selective towards hMAO-A. Compound 17 (Ki = 0.10 +/- 0.01 mu mol/L) was found to be equally potent and selective towards hMAO-B, when compared with the standard drug Selegiline (Ki = 0.12 0.01 p.mol/L). Nature and position of substitution in aryl ring at 2nd position of benzofuranone influences hMAO-B inhibitory potency, while their structural bulkiness influences selectivity between hMAO-A and hMAO-B. Molecular docking simulation was also carried out to understand the interaction of inhibitor with the enzyme at molecular level, and we found the docking results were in good agreement with the experimental values. Comparison of the activity profile of the aurones with their corresponding flavones reported earlier by our group revealed that there exists no difference in potency as well as selectivity. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2017.02.009
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 4-氰基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 4-<3-(2-Hydroxy-phenyl)-3-oxo-propen-(1)-yl>-benzonitril
  参考文献：
  名称：

  通过串联Oxa-Michael加成和氧化二氟甲基硫醇化合成3-HCF2S-色氨酸。

  摘要：

  描述了一种使用元素硫和ClCF2CO2Na作为二氟甲基硫醇化试剂合成二氟甲基硫醇化chromen-4-ones的简单方案。在碱性条件下，使用TEMPO作为氧化剂，在2'-羟基查耳酮，ClCF2CO2Na和硫的三组分反应下，可得到含HCF2S的4H-色烯-4-酮和9H-硫代[3,2-b]铬-9-酮衍生物产量高。该方案是实用且有效的，并且起始材料便宜且容易获得。

  DOI：

  10.1021/acs.orglett.9b03396

文献信息

• Synthesis and Antiviral Activity of 2-aryl-4H-chromen-4-one Derivatives Against Chikungunya Virus
  作者：Vishnu N. Badavath、Surender S. Jadav、Boris Pastorino、Xavier de Lamballerie、Barij N. Sinha、Venkatesan Jayaprakash

  DOI：10.2174/1570180813666160711163349

  日期：2016.10.31

  A series of nineteen 2-aryl-4H-chromen-4-one derivatives 2a-2s were synthesized and evaluated for their antiviral activity against Chikungunya virus (LR2006_OPY1) in Vero cell culture by CPE reduction assay. Three compounds 2a, 2b and 2g, were found to be active at concentration of (IC50) 0.44 M, 0.45 M and 2.02 M, respectively. Compounds having heterocyclic ring 2a and 2b at the 2nd position of the chromenone were found to be potent inhibitor of ChikV. Cytotoxicity studies were performed using Vero cell culture, compounds 2a and 2b exhibited SI of 100. Molecular docking simulation has been carried out to understand the possible mechanism of action.

  合成并评价了一系列十九种2-芳基-4H-色烯-4-酮衍生物2a-2s对Vero细胞培养中基孔肯雅病毒（LR2006_OPY1）的抗病毒活性，通过CPE减少试验。发现三种化合物2a、2b和2g在浓度（IC50）分别为0.44 M、0.45 M和2.02 M时具有活性。在色烯酮的2位具有杂环环的化合物2a和2b被发现是ChikV的强效抑制剂。通过Vero细胞培养进行了细胞毒性研究，化合物2a和2b显示出SI为100。进行了分子对接模拟以理解可能的作用机制。
• Graphite oxide: a metal free highly efficient carbocatalyst for the synthesis of 1,5-benzodiazepines under room temperature and solvent free heating conditions
  作者：Ramen Jamatia、Ajay Gupta、Binoyargha Dam、Mithu Saha、Amarta Kumar Pal

  DOI：10.1039/c6gc03110b

  日期：——

  We report a sustainable and metal free carbocatalyst, graphite oxide, for the synthesis of 1,5-benzodiazepines under room temperature and solvent free heating conditions.

  我们报告了一种在室温和无溶剂加热条件下合成1,5-苯并二氮杂pine的可持续且无金属的碳催化剂，氧化石墨。
• 一种二氟甲基硫化黄酮类化合物及其制备方法
  申请人：浙江大学

  公开号：CN110294730B

  公开（公告）日：2022-04-29

  本发明公开了一种二氟甲基硫化黄酮类化合物，其结构如式(I)所示；本发明还提供了所述二氟甲基硫化黄酮类化合物的制备方法，包括：在惰性气体保护，碱、氧化剂作用下，结构如式(II)所示的化合物、二氟氯乙酸钠和硫磺于有机溶剂中反应，反应结束经后处理得到所述二氟甲基硫化黄酮类化合物。本发明提供的制备方法，其原料廉价易得，合成方法简单，可大大降低成本。本发明提供的二氟甲基硫化黄酮类化合物可应用于生物活性分子以及药物合成等领域，具有广泛的用途。
• Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones
  作者：Vishnu Nayak Badavath、S. Ciftci-Yabanoglu、Soumendranath Bhakat、Ajay Kumar Timiri、Barij N. Sinha、G. Ucar、Mahmoud E.S. Soliman、Venkatesan Jayaprakash

  DOI：10.1016/j.bioorg.2014.11.008

  日期：2015.2

  A series of twenty 2-aryl-4H-chromen-4-one (flavones) derivatives (3a-3s) were synthesized and tested for hMAO inhibitory activity. Fifteen compounds (3a, 3c, 3e-3h, 3j-3p, 3r, 3s) were found to be selective towards MAO-B, while 3d was selective towards MAO-A, and 3b, 3i and 3q were non-selective. Experimental Selectivity Index for MAO-B ranges from 2.0 (3g, 3p) to 30.0 (3j). Compound 3j, which is carrying 3,4-di-OMeC6H3 groups at R position on the molecule, was found to be potent MAO-B inhibitor amongst the fifteen with K-i value for MAO-B of 0.16 +/- 0.01 mu M comparable to that of standard drug, Selegiline (Ki for MAO-B is 0.16 +/- 0.01 mu M). Compound 3j also appeared as the most selective MAO-B inhibitor according to its best selectivity index (30.0), which is comparable to that of Selegiline (SIMAO-B = 35.0). Molecular docking and molecular dynamics simulation studies were carried out using Autodock-4.0 and Amber12 to understand the molecular level interaction and energy relation of MAO isoforms with selective inhibitors (3d and 3j). Simulation results are in good agreement with the experimental results. Leads identified may further be explored to develop potent isoform specific inhibitors of MAO. (C) 2014 Elsevier Inc. All rights reserved.
• Discovery and Optimization of Chromenotriazolopyrimidines as Potent Inhibitors of the Mouse Double Minute 2−Tumor Protein 53 Protein−Protein Interaction
  作者：John G. Allen、Matthew P. Bourbeau、G. Erich Wohlhieter、Michael D. Bartberger、Klaus Michelsen、Randall Hungate、Robert C. Gadwood、Rick D. Gaston、Bruce Evans、Larry W. Mann、Michael E. Matison、Stephen Schneider、Xin Huang、Dongyin Yu、Paul S. Andrews、Andreas Reichelt、Alexander M. Long、Peter Yakowec、Evelyn Y. Yang、Tani Ann Lee、Jonathan D. Oliner

  DOI：10.1021/jm900681h

  日期：2009.11.26

  Tumor protein 53 (p53) is a critical regulator of cell cycle and apoptosis that is frequently disabled in human tumors. In many tumor types, p53 is deleted or mutated, but in others p53 is inactivated by overexpression or amplification of its negative regulator mouse double minute 2 (MDM2). A high-throughput screening effort identified 6,7-bis(4-bromophenyl)-7,12-dihydro-6H-chromeno[4,3-d]-[1,2,4]triazolo[1,5-a]pyrimidine as a potent inhibitor of the MDM2-p53 protein-protein interaction. This screening hit was found to be chemically unstable and difficult to handle due to poor DMSO solubility. Co-crystallization with the target protein helped to direct further optimization and provided a tractable lead series of novel MDM2-p53 inhibitors. In cellular assays, these compounds were shown to upregulate p53 protein levels and p53 signaling and to cause p53-dependent inhibition of proliferation and apoptosis.