2-(4-羟苯基)-3-甲基-4H-苯并吡喃-4-酮 | 55456-75-2

• 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-羟苯基)-3-甲基-4H-苯并吡喃-4-酮
• 英文名称: 3-methyl-4'-hydroxyflavone
• 英文别名: 2-(4-Hydroxyphenyl)-3-methyl-4H-chromen-4-one；2-(4-hydroxyphenyl)-3-methylchromen-4-one
• CAS: 55456-75-2
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: PDFKDSVRGSOSQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-羟苯基)-3-甲基-4H-苯并吡喃-4-酮 、 2-[2-[2-[2-[2-(2-羟基乙氧基)乙氧基]乙氧基]乙氧基]乙氧基]乙醇,甲磺酸 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以45%的产率得到1,19-bis[4'-((3-methyl)-4H-chromen-4-on-2-yl)phenyl]-1,4,7,10,13,16,19-heptaoxanonadecane
  参考文献：
  名称：

  Modulation of Multidrug Resistance Protein 1 (MRP1/ABCC1)-Mediated Multidrug Resistance by Bivalent Apigenin Homodimers and Their Derivatives

  摘要：

  Here we showed that bivalency approach is effective in modulating multidrug resistance protein 1 (MRP1/ABCC1)-mediated doxorubicin (DOX) and etoposide (VP16) resistance in human 2008/MRP1 ovarian carcinoma cells. Flavonoid dimers bearing five or six ethylene glycol (EG) units with 6-methyl (4e, 4f) or 7-methyl (5e, 5f) substitution on the ring A of flavonoid dimers have the highest modulating activity for DOX against MRP1 with an EC50 ranging from 73 to 133 nM. At 0.5 mu M, the flavonoid dimer 4e was sufficient to restore DOX accumulation in 2008/MRP1 to parental 2008/P level. Lineweaver-Burk and Dixon plot suggested that it is likely a competitive inhibitor of DOX transport with a K-i = 0.2 mu M. Our data suggest that flavonoid dimers have a high affinity toward binding to DOX recognition site of MRP1. This results in inhibiting DOX transport, increasing intracellular DOX retention, and finally resensitizing 2008/MRP1 to DOX. The present study demonstrates that flavonoid dimers can be employed as an effective modulator of MRP1-mediated drug resistance in cancer cells.

  DOI：

  10.1021/jm900194w
• 作为产物：
  描述：

  1-(2-hydroxyphenyl)-3-(4-hydroxyphenyl)-2-methylprop-2-en-1-one 在 碘 作用下， 以 二甲基亚砜 为溶剂， 以60%的产率得到2-(4-羟苯基)-3-甲基-4H-苯并吡喃-4-酮
  参考文献：
  名称：

  Jayashree; Alam, Afroze; Kumar, D. Vijay, Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 3, p. 237 - 240

  摘要：

  DOI：

文献信息

• 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。
• Flavanoids and Isoflavanoids for the prevention and treatment of cardiovascular diseases
  申请人：RESVERLOGIX CORP.

  公开号：EP2332527A2

  公开（公告）日：2011-06-15

  The present disclosure provides non-naturally occurring polyphenol compounds that upregulate the expression of Apolipoprotein A-l (ApoA-l). 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.

  本公开提供了可上调载脂蛋白 A-l（ApoA-l）表达的非天然多酚化合物。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疾病，如动脉粥样硬化等。
• Makrandi, J K; Kumari, Vandna, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 12, p. 1142 - 1144
  作者：Makrandi, J K、Kumari, Vandna

  DOI：——

  日期：——
• Jayashree; Alam, Afroze; Kumar, D. Vijay, Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 3, p. 237 - 240
  作者：Jayashree、Alam, Afroze、Kumar, D. Vijay、Nayak, Yogendra

  DOI：——

  日期：——