2-(2-硝基苯基)-2,3-二氢色烯-4-酮 | 107918-07-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 2-(2-硝基苯基)-2,3-二氢色烯-4-酮
• 英文名称: 2,3-dihydro-2-(2-nitrophenyl)-4H-1-benzopyran-4-one
• 英文别名: 2-(2-nitrophenyl)-2,3-dihydro-4H-chromen-4-one；2-(2-nitrophenyl)chroman-4-one；2‐(2‐nitrophenyl)‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐one；2-(2-Nitro-phenyl)-chroman-4-on；4H-1-Benzopyran-4-one, 2,3-dihydro-2-(2-nitrophenyl)-；2-(2-nitrophenyl)-2,3-dihydrochromen-4-one
• CAS: 107918-07-0
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: BEVZSBGPERALMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  124-125 °C
• 沸点：
  444.6±45.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-硝基苯基)-2,3-二氢色烯-4-酮 在 甲醇 、 sodium tetrahydroborate 作用下， 生成
  参考文献：
  名称：

  Phenotypic profiling enables the targeted design of a novel pseudo-natural product class

  摘要：

  DOI：

  10.1016/j.tet.2023.133553
• 作为产物：
  描述：

  (E)-2'-hydroxy-2-nitrochalcone 在 四溴化碳 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以84%的产率得到2-(2-硝基苯基)-2,3-二氢色烯-4-酮
  参考文献：
  名称：

  CBr4催化活化α,β-不饱和酮

  摘要：

  我们在这里表明，弱相互作用，如卤素键 (XB) 可用于激活 α,β-不饱和酮的羰基。四溴化碳 (CBr 4 ) 已被用作在无金属和无添加剂条件下从相应的 2'-羟基和 2'-氨基查耳酮选择性合成黄烷酮和氮杂黄烷酮的唯一试剂。DFT 计算支持 XB 在这些反应中查耳酮的氧和 CBr 4之间的催化作用。

  DOI：

  10.1039/d2ob01223e

文献信息

• Iodine catalyzed one-pot synthesis of flavanone and tetrahydropyrimidine derivatives via Mannich type reaction
  作者：Veerababurao Kavala、Chunchi Lin、Chun-Wei Kuo、Hulin Fang、Ching-Fa Yao

  DOI：10.1016/j.tet.2011.11.022

  日期：2012.1

  A variety of functionalized flavanone derivatives and tetrahydropyrimidine derivatives were achieved under remarkably mild conditions. The combination of good to excellent yields, a simple work-up, and the high compatibility of functional groups makes this an attractive synthetic approach to access flavanone and tetrahydropyrimidine derivatives.

  在非常温和的条件下获得了多种官能化的黄烷酮衍生物和四氢嘧啶衍生物。优良的产率与优异的产率，简单的后处理以及官能团的高度相容性的结合，使之成为获得黄烷酮和四氢嘧啶衍生物的一种有吸引力的合成方法。
• An efficient synthesis of flavanones and their docking studies with aldose reductase
  作者：D. D. Kondhare、G. Gyananath、Yasinalli Tamboli、Santosh S. Kumbhar、Prafulla B. Choudhari、Manish S. Bhatia、P. K. Zubaidha

  DOI：10.1007/s00044-017-1813-1

  日期：2017.5

  supported by the docking studies. Among the tested derivatives, 2, 3, 4-methoxy derivative 19 (IC50 5.88 ± 0.03 µM) exhibited the highest inhibitory activity whereas 2-methoxy derivative 12 showed the lowest, and the remaining compounds exhibited moderate activity with IC50 in the range of 6.09–7.89 µM. The spatial configuration of the most active derivative 19 was compared with pharmacophore requirements

  使用熔融氯化钙从2-羟基苯乙酮和苯甲醛合成了一系列黄烷酮衍生物，产率中等至中等，并且已对牛晶状体的醛糖还原酶纯化酶进行了体外醛糖还原酶抑制活性的测试。大多数合成的化合物都表现出有效的醛糖还原酶抑制活性，对接研究支持了所获得的结果。在测试的衍生物中，2，3，4-甲氧基衍生物19（IC 50 5.88±0.03 µM）表现出最高的抑制活性，而2-甲氧基衍生物12表现出最低的抑制活性，其余化合物对IC 50表现出中等的活性。范围为6.09–7.89 µM。使用分子建模系统，将活性最高的衍生物19的空间构型与醛糖还原酶抑制剂位点的药效基团要求进行了比较。
• Glycolytic Inhibition and Antidiabetic Activity on Synthesized Flavanone Scaffolds with Computer Aided Drug Designing Tools
  作者：Natarajan Kiruthiga、Govindaraj Saravanan、Chellappa Selvinthanuja、Kulandaivel Srinivasan、Thangavel Sivakumar

  DOI：10.2174/1570180817999201209204523

  日期：2021.8.10

  Diabetes mellitus is a challengeable metabolic disorder that leads to a group of complications when the HbA1c level is not maintained. Most of the existing drugs available in the market in long-term use may lead to serious adverse effects. Hence, current research focuses on drug development for the management of diabetes by synthesizing natural mimicking flavonoid analogues.

  This study focused on the synthesis of flavanone derivatives imitating natural flavonoid core and investigated for their antidiabetic and antioxidant activity, which can help in the development of drug discovery targeting diabetic management.

  The novel 2-phenyl-2,3-dihydro-chromen-4-ones were synthesized from 1,3-diphenyl-prop-2-en-1-one derivatives and characterized using UV, IR, ¹HNMR, ¹³CNMR and mass spectroscopic techniques. Drug target site was determined using graph theoretical analysis and screened the characterized title compounds for their in-silico studies by analyzing their physiochemical properties, ADMET studies, and molecular docking analysis. Antidiabetic and free radical scavenging effects were investigated both by in-vitro (alpha-amylase inhibitory assay) and in-vivo models. Streptozotocin (STZ) induced rats were used as in-vivo models.

  The α-amylase inhibitory assay showed flavanones with hydroxyl substitution HFA1- HFA7 had significant IC50 values. The test compounds (HFA3-HFA7) were investigated for their antidiabetic activity on STZ induced rats at 40 mg/kg. The blood glucose level and antioxidant enzymes were significantly restored by title compounds (HFA5, HFA4, and HFA6) with an electron-donating group such as hydroxyl, methoxy and thiophenyl group on ring B compared to glibenclamide.

  These results suggest that naturally mimicking synthesized flavanone have antidiabetic and antioxidant properties, which can aid in the development of drugs towards diabetes management.

  背景：糖尿病是一种具有挑战性的代谢紊乱，当HbA1c水平未得到控制时会导致一系列并发症。市场上现有的大部分长期使用的药物可能会导致严重的不良反应。因此，当前的研究重点在于通过合成天然模拟类黄酮类似物来开发治疗糖尿病的药物。 目标：本研究侧重于合成模拟天然类黄酮核心的黄酮衍生物，并对其抗糖尿病和抗氧化活性进行研究，这有助于开发针对糖尿病管理的药物发现。 材料和方法：从1,3-二苯基-丙-2-烯-1-酮衍生物合成了新型的2-苯基-2,3-二氢-香豆素，并利用紫外线、红外线、核磁共振、质谱等技术对其进行表征。通过图论分析确定了药物靶点位点，并通过对其物理化学性质、ADMET研究和分子对接分析进行了体外研究。通过体外（α-淀粉酶抑制实验）和体内模型研究了抗糖尿病和自由基清除效果。利用链脲霉素（STZ）诱导的大鼠作为体内模型。 结果：α-淀粉酶抑制实验显示，具有羟基取代的黄酮类物质HFA1-HFA7具有显著的IC50值。将试验化合物（HFA3-HFA7）以40 mg/kg剂量用于STZ诱导的大鼠，发现HFA5、HFA4和HFA6等具有电子给予基团（如羟基、甲氧基和硫苯基）的化合物明显恢复了血糖水平和抗氧化酶活性，与格列本脲相比。 结论：这些结果表明，天然模拟合成的黄酮类物质具有抗糖尿病和抗氧化性能，有助于开发针对糖尿病管理的药物。
• An efficient and facile synthesis of functionalized flavones from flavanones
  作者：Dasharath Kondhare、Anjaneyulu Kasa、Balaji Totawar、Venkat Bhadke、Harshad Lade

  DOI：10.1007/s13738-019-01801-4

  日期：2020.3

  scheme for the synthesis of 3-substituted functionalized flavones was developed. The reaction of flavanone and glyoxylic acid in ethanol in the presence of the catalytic amount of sulphuric acid at reflux temperature for 2–3 h yielded good to excellent functionalized flavones. As per present scenario for the synthesis of different substituted flavones, this method represents mild reaction conditions, low-cost

  开发了一种温和而有效的合成3-取代的功能性黄酮的方案。黄烷酮和乙醛酸在乙醇中的反应，在催化量的硫酸存在下，在回流温度下反应2–3 h，可以得到很好的官能化黄酮。按照目前用于合成不同取代的黄酮的方案，该方法代表了温和的反应条件，低成本的催化剂，广泛的底物范围以及高收率，这使其成为更加可靠和便捷的合成策略。
• Synthesis of flavanones using nanocrystalline MgO
  作者：B.M. Choudary、K.V.S. Ranganath、Jagajit Yadav、M. Lakshmi Kantam

  DOI：10.1016/j.tetlet.2004.12.078

  日期：2005.2

  The design and development of a truly nano heterogeneous catalyst for the Claisen-Schmidt condensation (CSC) of benz-aldehydes with 2-hydroxyacetophenone to yield substituted chalcones followed by isomerization to afford flavanones with excellent yields and selectivity is described. (C) 2005 Elsevier Ltd. All rights reserved.