2-(5-bromo-2-methoxyphenyl)chroman-4-one | 325779-18-8

• 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-(5-bromo-2-methoxyphenyl)chroman-4-one
• 英文别名: 2-(5-bromo-2-methoxyphenyl)-2,3-dihydro-4H-benzopyran-4-one；5'-bromo-2'-methoxyflavanone；2-(5-Bromo-2-methoxy-phenyl)chroman-4-one；2-(5-bromo-2-methoxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 325779-18-8
• 化学式: C₁₆H₁₃BrO₃
• 分子量: 333.181
• InChiKey: RQRDXBBPUVEJOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-溴-2-甲氧基苯甲醛 在 sodium acetate 、 potassium hydroxide 作用下， 以 甲醇 、 正丁醇 为溶剂， 反应 2.0h， 生成 2-(5-bromo-2-methoxyphenyl)chroman-4-one
  参考文献：
  名称：

  Development of Flavonoid-Based Inverse Agonists of the Key Signaling Receptor US28 of Human Cytomegalovirus

  摘要：

  A series of 31 chalcone- and flavonoid-based derivatives were synthesized in good overall yields and screened for their inverse agonist activity on the US28 receptor of human cytomegalovirus (HCMV). With one exception (e.g., 2-(5-bromo-2-methoxyphenyl)-3-hydroxy-4H-chromen-4-one), halogen-substituted flavonoids were, typically more potent inverse agonists than their related hydro derivatives. While toxicity could be used to partially explain the inverse agonist activity of some members of the series, 5-(benzyloxy)-2-(5-bromo-2-methoxyphenyl)-4H-chromen-4-one (11b) acted on the US28 receptor as a nontoxic, inverse agonist. The full inverse agonism (efficacy, -89%) and potency (EC50 = 3.5 mu M) observed with flavonoid lib is especially important as it provides both a new tool to study US28 signaling and a potential platform for the future development of HCMV-targeting drugs.

  DOI：

  10.1021/jm4003457

文献信息

• Synthesis and Investigation of Flavanone Derivatives as Potential New Anti-Inflammatory Agents
  作者：Cynthia Sinyeue、Mariko Matsui、Michael Oelgemöller、Frédérique Bregier、Vincent Chaleix、Vincent Sol、Nicolas Lebouvier

  DOI：10.3390/molecules27061781

  日期：——

  Flavonoids are polyphenols with broad known pharmacological properties. A series of 2,3-dihydroflavanone derivatives were thus synthesized and investigated for their anti-inflammatory activities. The target flavanones were prepared through cyclization of 2′-hydroxychalcone derivatives, the later obtained by Claisen–Schmidt condensation. Since nitric oxide (NO) represents an important inflammatory mediator

  黄酮类化合物是具有广泛已知药理特性的多酚。因此合成了一系列 2,3-二氢黄烷酮衍生物并研究了它们的抗炎活性。目标黄烷酮通过 2'-羟基查耳酮衍生物的环化制备，后者通过 Claisen-Schmidt 缩合获得。由于一氧化氮 (NO) 是一种重要的炎症介质，因此使用 Griess 试验在体外评估了各种黄烷酮对 LPS 诱导的 RAW 264.7 巨噬细胞中 NO 产生的影响。最活跃的化合物是黄烷酮 (4G)、2'-羧基-5,7-二甲氧基黄烷酮 (4F)、4'-溴-5,7-二甲氧基黄烷酮 (4D) 和 2'-羧基黄烷酮 (4J) ，IC50 值分别为 0.603、0.906、1.030 和 1.830 µg/mL。相比之下，松松素的 IC50 值为 203.60 µg/mL。因此，在这项工作中合成的衍生物与松松素相比具有更高的 NO 抑制能力，证明了药物调节对提高天然分子的生物学潜力的重要性。SAR
• FLAVONOID BASED ANTIVIRAL TARGETS
  申请人：PHANSTIEL, IV Otto

  公开号：US20150209323A1

  公开（公告）日：2015-07-30

  The present invention relates to novel compounds for modulating US28 receptor activity and methods for their use in preventing or treating US28 receptor-mediated disorders or conditions.

  本发明涉及一种新型化合物，用于调节US28受体活性以及预防或治疗US28受体介导的疾病或病状的方法。
• US9629822B2
  申请人：——

  公开号：US9629822B2

  公开（公告）日：2017-04-25
• [EN] FLAVONOID BASED ANTIVIRAL TARGETS<br/>[FR] CIBLES ANTIVIRALES À BASE DE FLAVONOÏDES
  申请人：UNIV CT FLORIDA RES FOUNDATION INC

  公开号：WO2014047551A1

  公开（公告）日：2014-03-27

  The present invention relates to novel compounds for modulating US28 receptor activity and methods for their use in preventing or treating US28 receptor-mediated disorders or conditions.
• Development of Flavonoid-Based Inverse Agonists of the Key Signaling Receptor US28 of Human Cytomegalovirus
  作者：Ana Kralj、Mai-Thao Nguyen、Nuska Tschammer、Nicolette Ocampo、Quinto Gesiotto、Markus R. Heinrich、Otto Phanstiel

  DOI：10.1021/jm4003457

  日期：2013.6.27

  A series of 31 chalcone- and flavonoid-based derivatives were synthesized in good overall yields and screened for their inverse agonist activity on the US28 receptor of human cytomegalovirus (HCMV). With one exception (e.g., 2-(5-bromo-2-methoxyphenyl)-3-hydroxy-4H-chromen-4-one), halogen-substituted flavonoids were, typically more potent inverse agonists than their related hydro derivatives. While toxicity could be used to partially explain the inverse agonist activity of some members of the series, 5-(benzyloxy)-2-(5-bromo-2-methoxyphenyl)-4H-chromen-4-one (11b) acted on the US28 receptor as a nontoxic, inverse agonist. The full inverse agonism (efficacy, -89%) and potency (EC50 = 3.5 mu M) observed with flavonoid lib is especially important as it provides both a new tool to study US28 signaling and a potential platform for the future development of HCMV-targeting drugs.