2-(3,4-dihydroxyphenyl)-6-hydroxy-4H-chromen-4-one | 263407-43-8

• 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: 2-(3,4-dihydroxyphenyl)-6-hydroxy-4H-chromen-4-one
• 英文别名: 6,3',4'-trihydroxyflavone；2-(3,4-dihydroxy-phenyl)-6-hydroxy-chromen-4-one；2-(3,4-Dihydroxy-phenyl)-6-hydroxy-chromen-4-on；2-(3,4-dihydroxyphenyl)-6-hydroxychromen-4-one
• CAS: 263407-43-8
• 化学式: C₁₅H₁₀O₅
• 分子量: 270.241
• InChiKey: BYVNWEGWXASECK-UHFFFAOYSA-N

物化性质

• 沸点：
  572.8±50.0 °C(Predicted)
• 密度：
  1.548±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3,4-dihydroxyphenyl)-6-hydroxy-4H-chromen-4-one 、 UDP-glucuronic acid 在 human UDP-glucuronosyltransferase 1A₉ 、 magnesium chloride 、 alamethicin 、 糖质酸-1,4-内酯 作用下， 生成
  参考文献：
  名称：

  Accurate Prediction of Glucuronidation of Structurally Diverse Phenolics by Human UGT1A9 Using Combined Experimental and In Silico Approaches

  摘要：

  通过实验使用145种酚类化合物，并通过3D-QSAR方法分析，确定了人UGT1A9的催化选择性。UGT1A9是一种重要的膜结合酶，催化外源性物质的葡糖醛酸化反应。通过动力学分析确定了UGT1A9的催化效率。使用CoMFA和CoMSIA技术分析了定量结构活性关系。通过将葡糖醛酸化位点及其相邻的芳香环重叠，实现了底物结构的最大立体重叠。对于具有多个活性葡糖醛酸化位点的底物，每个位点被视为单独的底物。3D-QSAR分析产生了统计上可靠的模型，具有良好的预测能力（CoMFA：q2=0.548，r2=0.949，r pred 2=0.775；CoMSIA：q2=0.579，r2=0.876，r pred 2=0.700）。通过轮廓系数图阐明了底物中负责选择性差异的结构特征。将轮廓系数图叠加在UGT1A9的同源模型的催化口袋中，能够高度自信地识别UGT1A9的催化口袋。CoMFA/CoMSIA模型可以预测底物的选择性和UGT1A9的体外清除率。我们的发现还提供了理解UGT1A9功能和底物选择性的可能分子基础。

  DOI：

  10.1007/s11095-012-0666-z
• 作为产物：
  描述：

  2-(3,4-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one 在 氢溴酸 作用下， 以 水 为溶剂， 反应 4.0h， 以37%的产率得到2-(3,4-dihydroxyphenyl)-6-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Inhibition of cytochrome P450 monooxygenase-catalyzed oxylipin formation by flavonoids: Evaluation of structure-activity relationship towards CYP4F2-selective inhibitors

  摘要：

  DOI：

  10.1016/j.ejmech.2022.114332

文献信息

• Design, synthesis and experimental validation of novel potential chemopreventive agents using random forest and support vector machine binary classifiers
  作者：Brienne Sprague、Qian Shi、Marlene T. Kim、Liying Zhang、Alexander Sedykh、Eiichiro Ichiishi、Harukuni Tokuda、Kuo-Hsiung Lee、Hao Zhu

  DOI：10.1007/s10822-014-9748-9

  日期：2014.6

  Compared to the current knowledge on cancer chemotherapeutic agents, only limited information is available on the ability of organic compounds, such as drugs and/or natural products, to prevent or delay the onset of cancer. In order to evaluate chemical chemopreventive potentials and design novel chemopreventive agents with low to no toxicity, we developed predictive computational models for chemopreventive agents in this study. First, we curated a database containing over 400 organic compounds with known chemoprevention activities. Based on this database, various random forest and support vector machine binary classifiers were developed. All of the resulting models were validated by cross validation procedures. Then, the validated models were applied to virtually screen a chemical library containing around 23,000 natural products and derivatives. We selected a list of 148 novel chemopreventive compounds based on the consensus prediction of all validated models. We further analyzed the predicted active compounds by their ease of organic synthesis. Finally, 18 compounds were synthesized and experimentally validated for their chemopreventive activity. The experimental validation results paralleled the cross validation results, demonstrating the utility of the developed models. The predictive models developed in this study can be applied to virtually screen other chemical libraries to identify novel lead compounds for the chemoprevention of cancers.

  与当前关于抗癌化疗药物的知识相比，关于有机化合物（如药物和/或天然产品）预防或延缓癌症发生的能力的信息非常有限。为了评估化学预防潜力并设计低毒至无毒的新型预防药物，本研究中我们开发了用于预防药物的预测计算模型。首先，我们构建了一个包含超过400种已知具有化学预防活性的有机化合物的数据库。基于该数据库，开发了多种随机森林和支持向量机二元分类器。所有得到的模型都通过交叉验证程序进行了验证。接着，将这些经过验证的模型应用于包含约23,000种天然产品及其衍生物的化学库进行虚拟筛选。根据所有经过验证模型的共识预测，我们筛选出了148种新型化学预防化合物。我们对这些预测具有活性的化合物进行了有机合成难易程度的进一步分析。最后，合成了18种化合物并实验验证了它们的化学预防活性。实验验证结果与交叉验证结果相符，证明了所开发模型的实用性。本研究中开发的预测模型可用于虚拟筛选其他化学库，以识别用于癌症化学预防的新型先导化合物。
• Preparation having antioxidant properties
  申请人：Merck Patent GmbH

  公开号：US20040067894A1

  公开（公告）日：2004-04-08

  The invention relates to a preparation having antioxidant properties, comprising at least one compound of the formula I 1 where R 1 to R 10 may be identical or different and are selected from H, OR 11 , straight-chain or branched C 1 - to C 20 -alkyl groups, straight-chain or branched C 3 - to C 20 -alkenyl groups, straight-chain or branched C 1 - to C 20 -hydroxyalkyl groups, where the hydroxyl group may be bonded to a primary or secondary carbon atom of the chain and furthermore the alkyl chain may also be interrupted by oxygen, and/or C 3 - to C 10 -cycloalkyl groups and/or C 3 - to C 12 -cycloalkenyl groups, where the rings may each also be bridged by —(CH 2 ) n — groups, where n=1 to 3, where all OR 11 are, independently of one another, OH, C 1 - to C 20 -alkoxy groups, C 3 - to C 20 -alkenyloxy groups, straight-chain or branched C 1 - to C 20 -hydroxyalkoxy groups and/or C 3 - to C 10 -cycloalkoxy groups and/or C 3 - to C 12 -cycloalkenyloxy groups, where the rings may each also be bridged by —(CH 2 ) n — groups, where n=1 to 3, and/or mono- and/or oligoglycosyl radicals, with the proviso that at least 3 radicals from R 1 to R 7 are OH and that at least 2 pairs of adjacent —OH groups are present in the molecule, or R 2 , R 5 and R 6 are OH and the radicals R 1 , R 3 , R 4 and R 7-10 are H.

  该发明涉及一种具有抗氧化性能的制剂，包括至少一种具有以下式I1的化合物，其中R1到R10可能相同也可能不同，选择自H、OR11、直链或支链的C1到C20烷基基团、直链或支链的C3到C20烯基基团、直链或支链的C1到C20羟基烷基基团，其中羟基可能连接到链的一级或二级碳原子上，此外，烷基链也可能被氧原子中断，和/或C3到C10环烷基基团和/或C3到C12环烯基基团，其中环可能也通过—(CH2)n—基团相互连接，其中n=1到3，其中所有的OR11都是独立的，OH、C1到C20烷氧基团、C3到C20烯氧基团、直链或支链的C1到C20羟基烷氧基团和/或C3到C10环烷氧基团和/或C3到C12环烯氧基团，其中环可能也通过—(CH2)n—基团相互连接，其中n=1到3，和/或单糖和/或寡糖基团，但至少3个从R1到R7的基团是OH，并且分子中至少有2对相邻的—OH基团，或者R2、R5和R6是OH，基团R1、R3、R4和R7-10是H。
• ANTIOXIDANTS
  申请人：Rudolph Thomas

  公开号：US20090246158A1

  公开（公告）日：2009-10-01

  The present invention relates to the use of compounds of the formula (I) where R stands for [lacuna] with radicals defined in the description, as antioxidants, to corresponding novel compounds and compositions, and to corresponding processes for the preparation of compounds and compositions.

  本发明涉及使用式(I)中R代表[空白]的化合物作为抗氧化剂，涉及相应的新化合物和组合物，以及制备化合物和组合物的相应过程。
• Anti-glycation agents for preventing age- diabetes- and smoking-related complications
  申请人：Yeboah Faustinus

  公开号：US20050043408A1

  公开（公告）日：2005-02-24

  The invention provides new inhibitors of protein glycation, identified from compound libraries by a high throughput screening assay. The anti-glycation agents so identified are characterized by a variety of chemical structures and are useful for the prevention or treatment of age-, diabetes-, and smoking-related complications, including neuropathy, nephropathy, ocular pathologies, or the loss of mechanical properties of collagenous tissues. Among compounds identified as having the anti-glycation activity, of special interest are epinephrine and its analogs, in particular D-epinephrine and its analogs, which are particularly useful for the prevention or treatment of age-, diabetes-, and smoking-related ocular pathologies.

  这项发明提供了新的蛋白质糖基化抑制剂，通过高通量筛选检测从化合物库中鉴定出来。所鉴定的抗糖基化剂具有多种化学结构，可用于预防或治疗与年龄、糖尿病和吸烟有关的并发症，包括神经病变、肾病、眼部病理或胶原组织的机械性能丧失。在被鉴定为具有抗糖基化活性的化合物中，特别感兴趣的是肾上腺素及其类似物，特别是D-肾上腺素及其类似物，可用于预防或治疗与年龄、糖尿病和吸烟有关的眼部病理。
• Flavonoid Complexes
  申请人：Carola Christophe

  公开号：US20080044364A1

  公开（公告）日：2008-02-21

  The invention relates to compounds of the formula I where R 1 to R 10 may be identical or different and are selected from H, OR 11 , straight-chain or branched C 1 - to C 20 -alkyl groups or hydroxyalkyl groups, straight-chain or branched C 3 - to C 20 -alkenyl groups and/or C 3 - to C 12 -cycloalkenyl groups, where the rings may each also be bridged by —(CH 2 ) n — groups, where n=1 to 3, where all OR 11 , independently of one another, stand for OH, C 1 - to C 20 -alkoxy groups, C 3 - to C 20 -alkenyloxy groups, straight-chain or branched C 1 - to C 20 -hydroxyalkoxy groups and/or C 3 - to C 10 -cycloalkoxy groups and/or C 3 - to C 12 -cycloalkenyloxy groups, where the rings may each also be bridged by —(CH 2 ) n — groups, where n=1 to 3, and/or mono- and/or oligoglycosyl radicals, CD stands for a cyclodextrin molecule, o stands for the number 1 and p stands for a number from the range 0.5 to 50, with the proviso that at least 2 radicals from R 1 to R 7 stand for OH and that at least 1 pair of adjacent —OH groups is present in the molecule.

  本发明涉及公式I的化合物，其中R1至R10可以相同或不同，选择自H、OR11、直链或支链C1至C20烷基或羟基烷基、直链或支链C3至C20烯基和/或C3至C12环烯基，其中环也可以由—（CH2）n—基桥接，其中n=1至3，其中所有的OR11独立地代表OH、C1至C20烷氧基、C3至C20烯氧基、直链或支链C1至C20羟基烷氧基和/或C3至C10环烷氧基和/或C3至C12环烯氧基，其中环也可以由—（CH2）n—基桥接，其中n=1至3，并/或单糖和/或寡糖基团，CD代表环糊精分子，o代表数字1，p代表范围0.5至50的数字，但至少有2个来自R1至R7的基团代表OH，并且分子中至少存在1对相邻的—OH基团。