3-hydroxy-2-(4-nitrophenyl)-4H-chromen-4-one | 83768-62-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-hydroxy-2-(4-nitrophenyl)-4H-chromen-4-one
• 英文别名: 3-hydroxy-2-(4-nitrophenyl)chromen-4-one
• CAS: 83768-62-1
• 化学式: C₁₅H₉NO₅
• 分子量: 283.24
• InChiKey: YECFKQSYRZNFMD-UHFFFAOYSA-N

物化性质

• 熔点：
  293-296 °C
• 沸点：
  472.8±45.0 °C(Predicted)
• 密度：
  1.522±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-(4-nitrophenyl)-4H-chromen-4-one 、 3-溴丙烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以185 mg的产率得到3-(allyloxy)-2-(4'-nitrophenyl)-4H-chromen-4-one
  参考文献：
  名称：

  通过 3-烯丙氧基黄酮的不对称重排对映选择性合成 3,4-氯二酮

  摘要：

  利用不对称钪 (III) 催化的 3-烯丙氧基黄酮重排以高产率和对映选择性制备手性、非外消旋 3,4-色二酮。这些合成中间体已被进一步细化为新型杂环骨架，包括角吡嗪和二氢吡嗪。重排产物的绝对构型最初是通过圆二色性 (CD) 的非经验分析使用时间相关密度泛函理论 (TDDFT) 计算确定的，并通过腙衍生物的 X 射线晶体学验证。该机制的初步研究支持可能通过苯并吡喃中间体进行的分子内重排途径。

  DOI：

  10.1021/jo100889c
• 作为产物：
  描述：

  1-(2-hydroxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one 在 双氧水 、 amylopectin sodium 作用下， 以 乙醇 为溶剂， 生成 3-hydroxy-2-(4-nitrophenyl)-4H-chromen-4-one
  参考文献：
  名称：

  使用碱性支链淀粉新型生物基催化剂催化一锅连续醇醛缩合/Algar-Flynn-Oyamada反应绿色获取黄酮醇

  摘要：

  在此，在化学机械干燥条件下制备碱性支链淀粉（AAp），通过碱容量、FT-IR、FESEM、TEM 和 TGA 分析进行表征，并作为新型生物有机碱催化剂用于一锅合成黄酮醇。基本容量为 7.3 mmolH2O -/g，AAp 催化初始羟醛缩合，并与过氧化氢配合进一步进行 Algar-Flynn-Oyamada 反应，得到高产率的黄酮醇抗氧化剂。因此，原位形成的2'-羟基查耳酮的第一次羟醛缩合或随后的氧化环化/羟基化在锅中成功进行，形成黄酮醇产品，而没有橙酮副产物。发现超分子碱催化剂AAp在重复使用五次后结构得到了很好的保存。该方案的优点是反应物可用、无苯醌副产物、反应时间短、产率高和催化剂可重复使用。 图形概要

  DOI：

  10.1007/s11164-023-05138-9

文献信息

• Flavonoids, 40.+ Synthesis of 3-alkyl- and -arylthioflavanones and their transformations into sulfur-containing flavonoids
  作者：Tamás Patonay、Erzsébet Patonay-Péli、György Litkei

  DOI：10.1016/s0040-4020(01)81494-0

  日期：1987.1

  trans-3-Mesyloxyflavanones 1 were converted into cis- and trans-3-(alkylthio)- and -(phenylthio) flavanones 2-4 by nucleophilic substitution reaction with thiols or thiolates. Flavanones 2-4 were useful intermediates in the synthesis of various sulfur-containing derivatives; flavanones, flavones and dihydrochalcones possessing alkyl- or arylthio, -sulfinyl and -sulfonyl group. Oxidation of cis- and trans- isomers

  通过与硫醇或硫醇盐的亲核取代反应，将反-3-甲氧基氧基黄烷酮1转化为顺式和反-3-（烷硫基）-和-（苯硫基）黄烷酮2-4。黄烷酮2-4是合成各种含硫衍生物的有用中间体。具有烷硫基或芳硫基，-亚磺酰基和-磺酰基的黄烷酮，黄酮和二氢查耳酮。4的顺式和反式异构体的氧化导致生成完全不同的产物。
• Exploring 3-Benzyloxyflavones as new lead cholinesterase inhibitors: synthesis, structure–activity relationship and molecular modelling simulations
  作者：Ehsan Ullah Mughal、Amina Sadiq、Momna Ayub、Nafeesa Naeem、Asif Javid、Sajjad Hussain Sumrra、Muhammad Naveed Zafar、Bilal Ahmad Khan、Fouzia Perveen Malik、Ishtiaq Ahmed

  DOI：10.1080/07391102.2020.1803136

  日期：2021.11.2

  molecular docking studies were carried out. HIGHLIGHTS 3-benzyloxyflavone analogues were designed, synthesized and characterized. The target molecules (1–10) were evaluated for their inhibitory potential against AChE and BChE inhibitory activities. Limited structure-activity relationship was developed based on the different substituent patterns on aryl part. Molecular docking studies were conducted to

  摘要 在该协议中，一系列 3-苄氧基黄酮衍生物已被设计、合成、表征和体外研究作为胆碱酯酶抑制剂。研究结果表明，所有合成的目标化合物 ( 1-10 ) 都是有效的乙酰胆碱酯酶 (AChE) 和丁酰胆碱酯酶 (BChE) 双重抑制剂，具有不同的 IC 50值。相比之下，它们对 AChE 的作用比 BChE 更有效。值得注意的是，除该系列中，化合物2被确定为既乙酰胆碱酯酶的最活跃的抑制剂（IC 50 = 0.05±0.01μM）和的BChE（IC 50 = 0.09±0.02μM）相对于标准多奈哌齐（IC 50= 0.09 ± 0.01（AChE）和 0.13 ± 0.04 μM（BChE）。此外，与标准品相比，衍生物5 (IC 50 = 0.07 ± 0.02 μM) 和10 (0.08 ± 0.02 μM) 对 AChE 表现出最高的选择性抑制。初步建立了构效关系，因此发现这些化合物的胆碱酯酶抑制活性高度依赖于
• An Expeditious Synthesis of Flavonols Promoted by Montmorillonite KSF Clay and Assisted by Microwave Irradiation under Solvent-Free Conditions
  作者：Mariappan Babu、Kasi Pitchumani、Penugonda Ramesh

  DOI：10.1002/hlca.201200336

  日期：2013.7

  A simple, efficient, rapid, and ecofriendly synthesis of flavonols in >90% yield from 2′‐(mesyloxy)epoxychalcones (=2‐(3‐aryl‐2,3‐epoxypropanoyl)phenyl methanesulfonates) promoted by montmorillonite KSF clay and assisted by microwave irradiation has been described.

  蒙脱石KSF粘土促进并辅助合成的2'-（甲氧基）环氧查尔酮（= 2-（3-芳基-2,3-环氧丙酰基）苯基甲磺酸盐）以简单，有效，快速且环保的方式合成黄酮醇，收率> 90％已经描述了通过微波辐射。
• Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies
  作者：Jamshaid Ashraf、Ehsan Ullah Mughal、Amina Sadiq、Maryam Bibi、Nafeesa Naeem、Anser Ali、Anam Massadaq、Nighat Fatima、Asif Javid、Muhammad Naveed Zafar、Bilal Ahmad Khan、Muhammad Faizan Nazar、Amara Mumtaz、Muhammad Nawaz Tahir、Masoud Mirzaei

  DOI：10.1080/07391102.2020.1805364

  日期：2021.12.12

  To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened forin vitroagainst mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis,H-1-,C-13-NMR) and mass spectrometry (EI-MS). The structure of compound15was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibioticsi.e.Cefixime and Clotrimazole. Amongst the series, the compounds2, 4, 5, 6, 7, 10, 11, 14and22exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound2(IC50= 0.280 +/- 0.010 mu g/ml) was found almost sixfold and derivative5(IC50= 0.230 +/- 0.020 mu g/ml) about sevenfold more active as compared to standard Kojic acid (IC50=1.79 +/- 0.6 mu g/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma
• Patonay, Tamas; Hegedues, Laszlo; Patonay-Peli, Erzsebet, Journal of Heterocyclic Chemistry, 1993, vol. 30, # 1, p. 145 - 151
  作者：Patonay, Tamas、Hegedues, Laszlo、Patonay-Peli, Erzsebet

  DOI：——

  日期：——