(E)-3-(5-bromo-2,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)-prop-2-en-1-one | 1443430-08-7

• 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: (E)-3-(5-bromo-2,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)-prop-2-en-1-one
• 英文别名: (E)-3-(5-bromo-2,4-dimethoxy-phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one；(E)-3-(5-bromo-2,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 1443430-08-7
• 化学式: C₁₇H₁₅BrO₄
• 分子量: 363.208
• InChiKey: KEKDEKFDMKYXED-BQYQJAHWSA-N

物化性质

• 熔点：
  153-157 °C
• 沸点：
  520.8±50.0 °C(predicted)
• 密度：
  1.438±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (E)-3-(5-bromo-2,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)-prop-2-en-1-one 在 双氧水 、 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.5h， 以81%的产率得到2-(5-bromo-2,4-dimethoxyphenyl)-3-hydroxy-4H-chromen-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
• 作为产物：
  描述：

  5-溴-2,4-二甲氧基苯甲醛 、 2'-羟基苯乙酮 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以94%的产率得到(E)-3-(5-bromo-2,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)-prop-2-en-1-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
• 作为试剂：
  描述：

  (E)-3-(5-bromo-2,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)-prop-2-en-1-one 、 双氧水 在 ice 、 (E)-3-(5-bromo-2,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)-prop-2-en-1-one 、 盐酸 、 2-(5-bromo-2,4-dimethoxyphenyl)-3-hydroxy-4H-chromen-4-one 作用下， 以 氢氧化钾 、 乙醇 为溶剂， 反应 19.5h， 生成 2-(5-bromo-2,4-dimethoxyphenyl)-3-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  FLAVONOID BASED ANTIVIRAL TARGETS

  摘要：

  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。

  公开号：

  US20150209323A1

文献信息

• 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.
• 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。