2-(4-羟基-3-甲氧基苯基)-4H-色烯-4-酮 | 4143-73-1

• 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-(4-羟基-3-甲氧基苯基)-4H-色烯-4-酮
• 英文名称: 4'-hydroxy-3'-methoxyflavone
• 英文别名: 4’-Hydroxy-3’-methoxyflavone；2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
• CAS: 4143-73-1
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: KTFLFGFPJQSPNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-羟基-3-甲氧基苯基)-4H-色烯-4-酮 、 tert-butyl bis(2-(2-(tosyloxy)ethoxy)ethyl)carbamate 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1,13-bis[4-(3-methoxy-4H-chromen-4-on-2-yl)phenyl]-1,4,10,13-tetraoxa-7-azatridecane
  参考文献：
  名称：

  Amine Linked Flavonoid Dimers as Modulators for P-Glycoprotein-Based Multidrug Resistance: Structure–Activity Relationship and Mechanism of Modulation

  摘要：

  Here we report a great improvement in reversal potency of cancer drug resistance when flavonoid dimers possess a functionally substituted aminopolyethylene glycol linker. The most potent compound, 18, contains a N-benzyl group at the linker. It has many advantages including (1) high potencies in reversing P-glycoprotein (P-gp) mediated resistance in LCC6MDR cells to various anticancer drugs with EC50 in the nanomolar range, (2) low toxicity and high therapeutic index, and (3) preferential inhibition of P-gp over multidrug resistance protein 1 and breast cancer resistance protein. Compound 18 stimulates P-gp-ATPase activity by 2.7-fold and mediates a dose-dependent inhibition of doxorubicin (DOX) transport activity. Lineweaver-Burk and Dixon plots suggest that 18 is a competitive inhibitor to DOX in binding to P-gp with a K-i of 0.28-0.34 mu M and a Hill coefficient of 1.17. Moreover, the LCC6MDR cell displays about 2.1-fold lower intracellular accumulation of 18 compared to the wild type, suggesting that 18 is a P-gp substrate as well.

  DOI：

  10.1021/jm201121b
• 作为产物：
  描述：

  在 吡啶 、 potassium hydroxide 、 溶剂黄146 、 盐酸 作用下， 以 水 、 甲醇 为溶剂， 反应 0.83h， 生成 2-(4-羟基-3-甲氧基苯基)-4H-色烯-4-酮
  参考文献：
  名称：

  Discovery of lesser known flavones as inhibitors of NF-κB signaling in MDA-MB-231 breast cancer cells—A SAR study

  摘要：

  Seventeen flavonoids with different substitutions were evaluated for inhibition of nuclear factor-kappa B (NF-kappa B) signaling in the invasive breast cancer cell line MDA-MB-231. They were screened using an engineered MDA-MB-231 cell line reporting NF-kappa B activation. The modulation of expression of two NF-kappa B regulated genes involved in tumorigenesis, matrix metalloproteinase-9 (MMP-9), and cyclooxygenase-2 (COX-2) were also analyzed in these cells. Among the compounds tested, all except gossypetin and quercetagetin inhibited the activation of NF-kappa B, and the expression of MMP-9 and COX-2 to different degree. Methylated flavone, chrysoeriol (luteolin-3'-methylether), was found to be the most potent inhibitor of MMP-9 and COX-2 expressions. The effect of chrysoeriol on cell proliferation, cell cycle, apoptosis and metastasis was analyzed by established methods. Chrysoeriol caused cell cycle arrest at G2/M and inhibited migration and invasion of MDA-MB-231 cells. The structure-activity relations amongst the flavonoids as NF-kappa B signaling inhibitors was studied. The study indicates differences between the actions of various flavonoids on NF-kappa B activation and on the biological activities of breast cancer cells. Flavones in general, were more active than the corresponding flavonols. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.07.093

文献信息

• TREATMENT OF DISEASES BY EPIGENETIC REGULATION
  申请人：McLure Kevin G.

  公开号：US20130281396A1

  公开（公告）日：2013-10-24

  The present disclosure provides non-naturally occurring polyphenol compounds that inhibit the bromodomain and extra terminal domain (BET) proteins. The disclosed compositions and methods can be used for treatment and prevention of cancer as well as sepsis, including NUT midline carcinoma, Burkitt's Lymphoma, Acute Myelogenous Leukemia, and Multiple Myeloma.

  本公开提供了抑制溴结构域和额外末端结构域（BET）蛋白的非天然存在的多酚化合物。所公开的组合物和方法可用于治疗和预防癌症以及败血症，包括NUT中线癌、Burkitt淋巴瘤、急性髓样白血病和多发性骨髓瘤。
• Flavanoids and isoflavanoids for the prevention and treatment of cardiovascular diseases
  申请人：Wong C.W. Norman

  公开号：US20060205767A1

  公开（公告）日：2006-09-14

  The present disclosure provides non-naturally occurring polyphenol compounds that upregulate the expression of Apolipoprotein A-I (ApoA-I). The disclosed compositions and methods can be used for treatment and prevention of cardiovascular disease and related disease states, including cholesterol or lipid related disorders, such as, e.g., atherosclerosis.

  本公开提供了非自然产生的多酚化合物，其可上调载脂蛋白A-I（ApoA-I）的表达。所公开的组合物和方法可用于治疗和预防心血管疾病及相关疾病状态，包括胆固醇或脂质相关障碍，例如动脉粥样硬化等。
• FLAVANOIDS AND ISOFLAVANOIDS FOR THE PREVENTION AND TREATMENT OF CARDIOVASCULAR DISEASES
  申请人：Wong Norman C.W.

  公开号：US20090259048A1

  公开（公告）日：2009-10-15

  The present disclosure provides non-naturally occurring polyphenol compounds that upregulate the expression of Apolipoprotein A-I (ApoA-I). The disclosed compositions and methods can be used for treatment and prevention of cardiovascular disease and related disease states, including cholesterol or lipid related disorders, such as, e.g., atherosclerosis.

  本公开提供了一些非自然生成的多酚化合物，它们可以上调载脂蛋白A-I（ApoA-I）的表达。所公开的组合物和方法可用于治疗和预防心血管疾病及相关疾病状态，包括胆固醇或脂质相关的疾病，如动脉粥样硬化等。
• Dual-Metal Single Atoms with Dual Coordination for the Domino Synthesis of Natural Flavones
  作者：Xin Zhao、Ruiqi Fang、Fengliang Wang、Xiangpeng Kong、Yingwei Li

  DOI：10.1021/jacsau.2c00582

  日期：2023.1.23

  The regulation of coordination configurations of single-atom sites is highly desirable to boost the catalytic performances of SA catalysts. Here, we demonstrate a versatile complexation-deposition strategy for the synthesis of 13 kinds of dual-metal SA site pairs with uniform and exclusive coordination configurations. The preparation is specifically exemplified by the fabrication of Cu and Co single-atom

  非常需要调节单原子位点的配位构型以提高SA催化剂的催化性能。在这里，我们展示了一种通用的络合沉积策略，用于合成 13 种具有统一和排他配位配置的双金属 SA 位点对。通过蚀刻和热解预合成的金属-有机框架模板，制备 Cu 和 Co 单原子对以及 N 和 P 杂原子共存，具体说明了该制备方法。系统表征揭示了 CuN 4 / CoN 3 P 1和 CuN 4 / CoN 2 P 2中 Cu 和 Co SA 位点的均匀且排他性配位构型，电子在其上不对称分布。令人印象深刻的是，与 CuN 4 / CoN 3 P 1和 CuN 4 / CoN 4对应物相比，CuN 4 / CoN 2 P 2位点对在多种天然类黄酮的合成中表现出显着增强的催化活性和选择性。理论计算结果表明，CuN 4 / CoN 2 P 2上的不对称电子分布位点可以通过降低关键中间体生成的能垒来促进氧分子的吸附和解离，从而在动力学上加速氧化偶联反应过程。
• Tire with rubber containing flavone
  申请人：THE GOODYEAR TIRE & RUBBER COMPANY

  公开号：EP1391327A1

  公开（公告）日：2004-02-25

  The invention relates to a rubber composition and a pneumatic tire having a component comprising a rubber containing the reaction product of a flavone and a methylene donor.

  本发明涉及一种橡胶组合物和充气轮胎，其成分包括含有黄酮和亚甲基供体反应产物的橡胶。