2-(3,4-二甲氧基苯基)-7-羟基苯并吡喃-4-酮 | 33513-36-9

• 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-(3,4-二甲氧基苯基)-7-羟基苯并吡喃-4-酮
• 英文名称: 2-(3,4-dimethoxy-phenyl)-7-hydroxy-chromen-4-one
• 英文别名: 7-Hydroxy-3',4'-dimethoxyflavon；2-(3,4-dimethoxyphenyl)-7-hydroxy-4H-chromen-4-one；7-hydroxy-3',4'-dimethoxyflavone；3',4'-dimethoxy-7-hydroxy-flavone；2-(3,4-dimethoxyphenyl)-7-hydroxychromen-4-one
• CAS: 33513-36-9
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: MEDOAKSPIIOKFU-UHFFFAOYSA-N

物化性质

• 熔点：
  255 °C
• 沸点：
  501.5±50.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  2-(3,4-二甲氧基苯基)-7-羟基苯并吡喃-4-酮 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 44.0h， 生成 2-[2-(3,4-dimethoxyphenyl)-4-oxochromen-7-yl]oxyacetohydrazide
  参考文献：
  名称：

  Ahluwalia, V. K.; Goyal, Madhuri; Jain, Anjula, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 381 - 383

  摘要：

  DOI：
• 作为产物：
  描述：

  原儿茶酸 在 sodium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 9.0h， 生成 2-(3,4-二甲氧基苯基)-7-羟基苯并吡喃-4-酮
  参考文献：
  名称：

  Flavone-Based Novel Antidiabetic and Antidyslipidemic Agents

  摘要：

  The hybrid congeners 62-90 of 6- and 7-hydroxyflavones with aminopropanol have been synthesized and evaluated for their antidiabetic activity in sucrose-challenged low-dosed streptozotocin (STZ)-induced diabetic rats and db/db mice. The optical enantiomers 70a, 706, 90a, and 906 of two congeners 70 and 90 exhibiting consistent antidiabetic and antidyslipidemic activities were also prepared, and their antidiabetic activity results indicate its association mainly with S isomers. These compounds also lower cholesterol and TG profiles while improving high-density lipoprotein cholesterol to CHOL ratio in db/db mice. The bioavailability of compound 70 and its isomer varies between 27 and 29% whereas that of the more polar compound 90a is poor as determined in rat by oral and intraperitoneal administrations.

  DOI：

  10.1021/jm201107g

文献信息

• Exploration of multi-target potential of chromen-4-one based compounds in Alzheimer’s disease: Design, synthesis and biological evaluations
  作者：Manjinder Singh、Maninder Kaur、Nirmal Singh、Om Silakari

  DOI：10.1016/j.bmc.2017.09.012

  日期：2017.12

  A novel series of flavonoid based compounds were designed, synthesized and biologically evaluated for Acetylcholinesterase (AChE) inhibitory activity integrated with advanced glycation end products (AGEs) inhibitory and antioxidant potential. Most of the derivatives inhibited AChE in nanomolar IC50 range along with good AGEs inhibitory and radical scavenging activity. Among them, 7m, strongly inhibited

  设计，合成和生物评估了一系列基于类黄酮的新型化合物，并结合了先进的糖基化终产物（AGEs）抑制和抗氧化潜力，对乙酰胆碱酯酶（AChE）的抑制活性进行了生物学评估。大多数衍生物在纳摩尔IC 50范围内均能抑制AChE，并具有良好的AGEs抑制和自由基清除活性。其中7m强烈抑制AChE（IC 50  = 5.87 nM），并且与参考药物多奈哌齐（IC 50）相比具有较强的抑制作用。 = 12.7 nM）。通过对接分析证明了其有效的抑制活性，该对接分析揭示了其与AChE的CAS（催化活性位点）和PAS（外围阴离子位点）同时具有双重结合特性。此外，该化合物还具有防止晚期糖基化终产物形成的能力（IC 50  = 23.0 µM），并具有额外的自由基清除性能（IC 50  = 37.12 nM）。它（7m）还通过使用莫里斯水迷宫试验改善了东pol碱引起的小鼠记忆力减退。因此，类黄酮作为潜在的多官能抗阿
• Design, synthesis and apoptosis inducing activity of nonsteroidal flavone-methanesulfonate derivatives on MCF-7 cell line as potential sulfatase inhibitor
  作者：Mahdiyeh H. S. Javadi、Aida Iraji、Maliheh Safavi、Hamed Montazeri、Parastoo Tarighi、Samane Eftekhari、Latifeh Navidpour、Seyedeh Sara Mirfazli

  DOI：10.1007/s00044-021-02767-w

  日期：2021.9

  optimization was conducted to design novel flavone-sulfonates pharmacophore as a new steroid sulfatase inhibitor. In the present work, the conventional methods for the synthesis of 4-oxo-2-phenyl-4H-chromen-7-yl methanesulfonate derivatives were reported. Their cytotoxicity was evaluated with MTT assay against a breast cancer cell line (MCF-7). The apoptosis inducing activity of the most cytotoxic compound

  近年来，专注于具有选择性活性的新型强效抗癌药物是癌症治疗的最大挑战之一。乳腺癌是最常见的癌症，也是女性癌症死亡的主要原因。硫酸酯酶在将硫酸化类固醇转化为非硫酸化类固醇激素方面发挥着重要作用，这会增加许多激素依赖性癌症（如乳腺癌）的生长和发展。在这方面，进行了基于结构的优化以设计新的黄酮磺酸盐药效团作为新的类固醇硫酸酯酶抑制剂。在目前的工作中，合成 4-oxo-2-phenyl-4 H的常规方法报道了-chromen-7-yl 甲磺酸酯衍生物。它们的细胞毒性通过 MTT 测定对乳腺癌细胞系 (MCF-7) 进行评估。在雌二醇是癌细胞存活的关键生长因子的情况下，与多西紫杉醇相比，评估了最具细胞毒性的化合物3c的凋亡诱导活性，IC 50值为 0.615 µM。双染色Annexin V-FITC/PI分析结果表明该化合物3c在MCF-7细胞中的细胞毒活性通过细胞凋亡发生。进行了分子对接研究以阐明最有希望的化合物（3c）的抑制模式)
• [EN] OXY SUBSTITUTED FLAVONES AS ANTIHYPERGLYCEMIC AND ANTIDYSLIPIDEMIC AGENTS<br/>[FR] FLAVONES SUBSTITUES PAR HYDROXY UTILISES EN TANT QU'AGENTS ANTI-HYPERGLYCEMIQUES ET ANTI-DYSLIPIDEMIQUES
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2006040621A1

  公开（公告）日：2006-04-20

  The present invention provides novel substituted flavone derivatives which exhibit anti­ hyperglycemic and antidyslipedemic activity. The invention also provides a method for controlling type ii diabetes and associated hyperlipidemic conditions in a mammal by administering compound of the present invention and compositions containing these derivatives.

  本发明提供了新颖的取代黄酮衍生物，表现出抗高血糖和抗血脂异常活性。该发明还提供了一种通过给予本发明化合物和含有这些衍生物的组合物来控制哺乳动物中II型糖尿病和相关高血脂症状的方法。
• Process for the preparation of flavone derivatives
  申请人：——

  公开号：US20040059100A1

  公开（公告）日：2004-03-25

  The invention relates to a process for the preparation of flavone derivatives in which a 2-hydroxyacetophenone compound is metallated using a lithium compound at low temperatures and subsequently reacted with a keto compound, and where the ratio of the molar equivalents of lithium compound to the 2-hydroxyacetophenone compound functional groups to be metallated is from 1 to 1.2. The resultant &bgr;-diketone compound is subsequently cyclised with warming in an acidic medium.

  本发明涉及一种制备黄酮衍生物的方法，其中使用锂化合物在低温下对2-羟基苯乙酮化合物进行金属化，然后与酮化合物反应，所述锂化合物的摩尔当量与要金属化的2-羟基苯乙酮化合物的官能团的比例为1至1.2。随后，在酸性介质中加热使所得的β-二酮化合物环化。
• Oxy substituted flavones as antihyperglycemic and antidyslipidemic agents
  申请人：Pratap Ram

  公开号：US20060178373A1

  公开（公告）日：2006-08-10

  The present invention provides novel substituted flavone derivatives which exhibit anti-hyperglycemic and antidyslipedemic activity. The invention also provides a method for controlling type II diabetes and associated hyperlipidemic conditions in a mammal by administering compound of the present invention and compositions containing these derivatives.

  本发明提供了一种新型的取代黄酮衍生物，该衍生物表现出抗高血糖和抗血脂异常的活性。本发明还提供了一种通过给予本发明化合物和含有这些衍生物的组合物来控制哺乳动物的II型糖尿病和相关高脂血症状的方法。

表征谱图