2',4'-dihydroxy-4-chlorochalcone | 36745-24-1

• 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: 2',4'-dihydroxy-4-chlorochalcone
• 英文别名: 4-Chlor-2',4'-dihydroxy-chalkon；2',4'-Dihydroxy-4-chloro chalcone；3-(4-chlorophenyl)-1-(2,4-dihydroxyphenyl)prop-2-en-1-one
• CAS: 36745-24-1
• 化学式: C₁₅H₁₁ClO₃
• 分子量: 274.704
• InChiKey: AQASVHPTJNWRJB-UHFFFAOYSA-N

物化性质

• 熔点：
  253-255 °C(Solv: ethanol (64-17-5))
• 沸点：
  485.9±37.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2',4'-dihydroxy-4-chlorochalcone 在 mercury(II) diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以54%的产率得到4′-chloro-6-hydroxyaurone
  参考文献：
  名称：

  Synthesis, docking studies and antioxidant activity of some chalcone and aurone derivatives

  摘要：

  Chalcones and aurones are found to possess high antioxidant activity. They are known to inhibit tyrosinase enzyme involved in synthesis of melanin. A series of substituted chalcones and aurones have been synthesized and tested for their antioxidant activity. Postulated structures of the newly synthesized compounds are in agreement with their IR, H-1 NMR and MS. The docking study of this series of compounds was performed on crystal structure of tyrosinase from Bacillus megaterium using VlifeMDS 3.0 software. Antioxidant activity data obtained from four methods, i.e., DPPH free radical scavenging assay, iron chelating assay, reducing power assay and hydrogen peroxide scavenging assay, indicate that the activity increased with dimethylamino group on position 4/4' of ring B as evident from the significant activities of SB7 and SB8 in case of chalcones and aurones, respectively. The poor activities of SB4 and SB5 in DPPH scavenging ability and reducing power assays could be because of presence of chloro group on B-ring. Furthermore, the activity is facilitated with the presence of hydroxyl group on A-ring (preferably on position 5/5') in both chalcones and aurones.

  DOI：

  10.1007/s00044-012-0413-3
• 作为产物：
  描述：

  2-羟基-4-(四氢吡喃-2-基氧基)苯乙酮 在 盐酸 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 28.0h， 生成 2',4'-dihydroxy-4-chlorochalcone
  参考文献：
  名称：

  查尔酮衍生物作为潜在的抗念珠菌制剂的设计，合成，生物学活性和构效关系研究。

  摘要：

  外阴念珠菌病（VVC）每年都会影响全球数百万妇女。白色念珠菌是女性中最常见的病原体，其对一线和二线疗法产生抗药性的快速能力促进了对新的有效抗真菌剂的寻找。在这项研究中，我们显示了十五种合成查尔酮类似物的体外抗念珠菌活性及其在VVC体内模型中的抗真菌潜力。查耳酮12具有较强的抗真菌作用，能够抑制假丝酵母菌的生长。浓度为15.6 µg mL -1。另外，作用机理研究表明麦角固醇真菌膜是该化合物的靶标。尽管具有相当大的抗真菌活性，查耳酮12在肾细胞谱系中显示出高细胞毒性。此外，该化合物能够减少念珠菌相关的毒力，损害白色念珠菌中的酵母-菌丝过渡。VVC的体内模型显示查尔酮12大大降低了真菌的负荷。综上所述，这些发现表明查耳酮12是体外有效的抗念珠菌剂，除了在CVV模型中有助于改善真菌感染外。然而，它显示出低选择性和高毒性，表明分子修饰以最小化这些特性。

  DOI：

  10.1038/s41429-018-0048-9

文献信息

• Design, synthesis, and in vitro hMAO-B inhibitory evaluation of some 1-methyl-3,5-diphenyl-4,5-dihydro-1H-pyrazoles
  作者：Rossella Fioravanti、Nicoletta Desideri、Mariangela Biava、Luca Proietti Monaco、Laura Grammatica、Matilde Yáñez

  DOI：10.1016/j.bmcl.2013.07.035

  日期：2013.9

  A series of 1-methyl-3,5-diphenyl-4,5-dihydro-1H-pyrazoles (3a–k and 4a–u) were designed, synthesized, and evaluated for their inhibitory efficacy towards the two hMAO isoforms. Most of the derivatives were found to be potent and selective hMAO-B inhibitors. In particular, derivative 3g showed greater hMAO-B affinity than selective inhibitor selegiline coupled with high selectivity index (SI = 145)

  设计，合成了一系列1-甲基-3,5-二苯基-4,5-二氢-1 H-吡唑类化合物（3a - k和4a - u），并评估了它们对两种hMAO同工型的抑制作用。发现大多数衍生物是有效的和选择性的hMAO-B抑制剂。尤其是，衍生物3g与选择性抑制剂司来吉兰相比具有更高的hMAO-B亲和力，并具有高选择性指数（SI = 145）。最具选择性的hMAO-B抑制剂是3-甲基类似物3f，SI高于909。
• 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。
• Venkataraman, Setaraman; Jain, Saras; Shah, Kamal, Acta poloniae pharmaceutica, 2010, vol. 67, # 4, p. 361 - 366
  作者：Venkataraman, Setaraman、Jain, Saras、Shah, Kamal、Upmanyu, Neeraj

  DOI：——

  日期：——
• Chromone derivatives bearing pyridinium moiety as multi-target-directed ligands against Alzheimer’s disease
  作者：Shahin Abdpour、Leili Jalili-Baleh、Hamid Nadri、Hamid Forootanfar、Syed Nasir Abbas Bukhari、Ali Ramazani、Seyed Esmaeil Sadat Ebrahimi、Alireza Foroumadi、Mehdi Khoobi

  DOI：10.1016/j.bioorg.2021.104750

  日期：2021.5