2,4-dichloro-2'-hydroxychalcone

• 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: 2,4-dichloro-2'-hydroxychalcone
• 英文别名: 3-(2,4-dichlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one；3-(2,4-dichlorophenyl)-1-(2-hydroxyphenyl)-2-propenone；2,4-Dichlor-2'-hydroxy-benzalacetophenon；1-(2-Hydroxy-phenyl)-3-(2,4-dichlor-phenyl)-propen-1-on；3-(2,4-dichloropheny)-1-(2-hydroxyphenyl)-2-propen-1-one；2,4-Dichlor-2'-hydroxy-chalkon
• 化学式: C₁₅H₁₀Cl₂O₂
• 分子量: 293.149
• InChiKey: BPYVYBKYFSXRCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-2'-hydroxychalcone 在 盐酸 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以77.6%的产率得到2',4'-dichloroflavanone
  参考文献：
  名称：

  Glycolytic Inhibition and Antidiabetic Activity on Synthesized Flavanone Scaffolds with Computer Aided Drug Designing Tools

  摘要：

  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。

  DOI：

  10.2174/1570180817999201209204523
• 作为产物：
  描述：

  2,4-二氯苯胺 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2,4-dichloro-2'-hydroxychalcone
  参考文献：
  名称：

  GUDI; HIREMATH; BADIGER, Archiv der Pharmazie, 1962, vol. 295 /67, p. 16 - 19

  摘要：

  DOI：

文献信息

• Water-mediated phosphorylative cyclodehydrogenation: An efficient preparation of flavones and flavanones
  作者：Manorama Vimal、Uma Pathak、Anand Kumar Halve

  DOI：10.1080/00397911.2019.1643484

  日期：——

  for the conversion of 2′-hydroxychalcones to flavanones and flavones has been developed. The reagent efficiently promoted one-pot conversion of 2′-hydroxychalcones to flavones through flavanones involving cyclization and oxidative dehydrogenation. By changing the stoichiometery of the reagents, the reaction can be tuned to generate either flavanone or flavone. The developed protocol was found to be applicable

  摘要 开发了一种利用 POCl3-水将 2'-羟基查耳酮转化为黄烷酮和黄酮的新合成策略。该试剂通过涉及环化和氧化脱氢的黄烷酮有效地促进了 2'-羟基查尔酮向黄酮的一锅法转化。通过改变试剂的化学计量，可以调整反应以生成黄烷酮或黄酮。发现开发的协议适用于各种 2'-羟基查尔酮。图形概要
• Cyclization of 2′-hydroxychalcones to flavones using ammonium iodide as an iodine source: An eco-friendly approach
  作者：Pramod Kulkarni、Dasharath Kondhare、Ravi Varala、Pudukulathan Zubaidha

  DOI：10.2298/jsc120901119k

  日期：——

  Ammonium iodide in open air decomposes to ammonia and iodine. The in situ generated iodine has been used for cyclization of 2?-hydroxychalcones to corresponding flavones under solvent free conditions with good to excellent yields. This method would serve as an attractive alternative to the existing methods for synthesis of flavones and use of toxic molecular iodine is avoided.

  碘化铵在露天会分解成氨和碘。原位生成的碘 生成的碘被用于在无溶剂条件下将 2? 在无溶剂条件下环化成相应的黄酮类化合物，并获得良好甚至极好的产率。 产率。这种方法可以替代现有的 黄酮合成方法的一种有吸引力的替代方法，而且可以避免使用有毒的碘分子。 避免使用有毒的分子碘。
• Nanosilica-supported dual acidic ionic liquid as a heterogeneous and reusable catalyst for the synthesis of flavanones under solvent-free conditions
  作者：Shahnaz Rostamizadeh、Negar Zekri、Leili Tahershamsi

  DOI：10.1007/s10593-015-1728-z

  日期：2015.6

  A nanosilica-supported dual acidic ionic liquid on the basis of 1-methyl-3-(4-sulfobutyl)imidazolium hydrogen sulfate was synthesized and used as an efficient, green, non-corrosive, non-toxic, heterogeneous, and reusable catalyst for the synthesis of some new and known substituted flavanones. The synthesis was done by the condensation of 2'-hydroxyacetophenone with different aldehydes and the subsequent

  以1-甲基-3-（4-磺丁基）咪唑硫酸氢盐为基础，合成了纳米二氧化硅负载的双酸性离子液体，并用作高效，绿色，无腐蚀，无毒，多相且可重复使用的催化剂。一些新的和已知的取代的黄烷酮的合成。合成是通过2'-羟基苯乙酮与不同的醛缩合并随后在催化剂的存在下将所得2'-羟基查耳酮环化来完成的。这种新方法的特点是产品收率高，反应时间短和无溶剂条件。
• <i>In Vitro</i>Enzyme Inhibition Potentials and Antioxidant Activity of Synthetic Flavone Derivatives
  作者：Mohammad Shoaib、Syed Wadood Ali Shah、Niaz Ali、Ismail Shah、Muhammad Naveed Umar、Shafiullah、Muhammad Ayaz、Muhammad Nawaz Tahir、Sohail Akhtar

  DOI：10.1155/2015/516878

  日期：——

  Free radicals are produced by an important chemical process known as oxidation that in turn initiates chain reactions to damage the cells and originate oxidative stress. Flavones have got special position in research field of natural and synthetic organic chemistry due to their biological capabilities as antioxidant. The antioxidants are known to possess extensive biological effects that include antiviral, antibacterial, anti-inflammatory, antithrombotic, and vasodilatory activities. The simple flavone (F1) and substituted flavone derivatives (F2–F5) have been synthesized fromo-hydroxyacetophenone and benzaldehyde derivatives in good yield. The structures have been established by different spectroscopic techniques like¹H NMR,¹³C NMR, IR, and elemental analysis. Antioxidant profile of these compounds was established using DPPH and H₂O₂free radical scavenging assay. The findings showed that halogenated flavones showed more enzyme inhibitions and antioxidant activities than simple flavones and are potential candidates for the treatment of wide range of diseases.

  自由基是通过一种重要的化学过程氧化产生的，这进而引发链式反应来损伤细胞并产生氧化应激。由于它们作为抗氧化剂的生物学能力，黄酮类化合物在天然和合成有机化学研究领域中占据着特殊的地位。抗氧化剂被认为具有广泛的生物效应，包括抗病毒、抗菌、抗炎、抗血栓和扩血管活性。简单的黄酮类化合物（F1）和取代的黄酮类衍生物（F2-F5）已经从邻羟基苯乙酮和苯甲醛衍生物中以良好的产率合成。这些化合物的结构已通过不同的光谱技术（如1H NMR、13C NMR、IR和元素分析）确定。使用DPPH和H2O2自由基清除实验建立了这些化合物的抗氧化剖面。研究结果表明，卤代黄酮类化合物显示出比简单黄酮类化合物更多的酶抑制和抗氧化活性，是治疗各种疾病的潜在候选药物。
• Syntheses of 1,5-Benzothiazepines: Part-50: 8-Substituted 2,3/2,5-dihydro-2,4-diaryl-1,5-benzothiazepines as Potential Antimicrobial Agents
  作者：Seema Pant、Rajkumari Jadon、Anil Kumar Bharti

  DOI：10.14233/ajchem.2018.20960

  日期：——

  The syntheses of two novel series of 8-substituted 2,5-dihydro-2,4-bis(2,4-dichlorophenyl)-1,5-benzothiazepines and 8-substituted 2,3-dihydro-2-(2,4-dichlorophenyl)-4-(2-hydroxyphenyl)-1,5-benzothiazepines being reported herein were achieved by the reactions of 5-substituted 2-aminobenzenethiols, the substituents being fluoro, chloro, bromo, methyl, methoxy, ethoxy, with α,β-unsaturated carbonyl compounds. The enolizable ketone, 1,3-bis(2,4-dichlorophenyl)-2-propenone, or 3-(2,4-dichlorophenyl)-1-(2-hydroxyphenyl)-2-propenone, was reacted with the 5-substituted 2-aminobenzenethiols in dry ethanol containing trifluoroacetic acid, to obtain 12 new compounds, 8-substituted 2,3/2,5-dihydro-2,4-diaryl-1,5-benzothiazepines by Michael type condensation reaction. The products were characterized on the basis of micro analytical data and spectral analysis comprising IR, 1H NMR and mass spectral studies. All the compounds were screened for antimicrobial activity, against the Gram-positive Staphylococcus aureus and Gram-negative bacteria, Enterobacter cloacae and Klebsiella aerogenes with various reference drugs, Vancomycin for Staphylococcus aureus and Enterobacter cloacae, polymyxin B for Klebsiella aerogenes and against the fungus Candida albicans with reference drug fluconazole.

  本文报告了两系列新型8取代的2,5-二氢-2,4-双(2,4-二氯苯)-1,5-苯噻氮烯和8取代的2,3-二氢-2-(2,4-二氯苯)-4-(2-羟基苯)-1,5-苯噻氮烯的合成，这些合成是通过5取代的2-氨基苯硫醇与α,β-不饱和羰基化合物反应实现的。可酮化的酮类化合物1,3-双(2,4-二氯苯)-2-丙烯酮或3-(2,4-二氯苯)-1-(2-羟基苯)-2-丙烯酮与在含有三氟乙酸的干燥乙醇中的5取代2-氨基苯硫醇反应，获得12种新化合物，通过迈克尔型缩合反应生成8取代的2,3/2,5-二氢-2,4-二芳-1,5-苯噻氮烯。产品的表征基于微量分析数据和红外光谱、1H NMR及质谱研究。所有化合物均进行了抗微生物活性筛选，针对革兰氏阳性菌金黄色葡萄球菌和革兰氏阴性菌肠杆菌及克雷伯氏菌，使用不同的参考药物，金黄色葡萄球菌和肠杆菌的参考药物为万古霉素，克雷伯氏菌的参考药物为多粘菌素B，以及针对真菌白色念珠菌的参考药物氟康唑。