(+/-)-8-n-Propylnaringenin

• 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: (+/-)-8-n-Propylnaringenin
• 英文别名: 8-n-propyl-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one；5,7-dihydroxy-2-(4-hydroxyphenyl)-8-propyl-3,4-dihydro-2H-1-benzopyran-4-one；5,7-dihydroxy-2-(4-hydroxyphenyl)-8-propyl-2,3-dihydrochromen-4-one
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: PFCDDRUHZAMKHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  (+/-)-8-n-Propylnaringenin 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以75%的产率得到6-chloro-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-propylchromen-4-one
  参考文献：
  名称：

  6,8-SUBSTITUTED NARINGENIN DERIVATIVE AND USE THEREOF

  摘要：

  本发明公开了一种6,8-取代的柚皮素衍生物，如式（I）所示：其中，式（I）中的A6和A8分别选自H、卤素、羟基、含1-3个碳原子的烷基、直链烯基、醇基、醛基或含2-3个碳原子的羧酸基，通过对柚皮素进行改性而得到，或其药学上可接受的盐，其制备方法以及用于制备改善呼吸系统功能和缓解咳嗽药物的用途。

  公开号：

  US20160130245A1
• 作为产物：
  描述：

  2-n-propyl-1,3,5-trimethoxybenzene 在 盐酸 、 氢氧化钾 、 sodium acetate 、 三溴化硼 、 四氯化锡 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 44.0h， 生成 (+/-)-8-n-Propylnaringenin
  参考文献：
  名称：

  Subtle Side-Chain Modifications of the Hop Phytoestrogen 8-Prenylnaringenin Result in Distinct Agonist/Antagonist Activity Profiles for Estrogen Receptors α and β

  摘要：

  In search of therapeutic agents for estrogen-related pathologies, phytoestrogens are being extensively explored. In contrast to naringenin, 8-prenylnaringenin is a potent hop-derived estrogenic compound, highlighting the importance of the prenyl group for hormonal activity. We investigated the effects of substituting the prenyl group at C(8) with alkyl chains of varying lengths and branching patterns on estrogen receptor (ER) subtype ER alpha- and ER beta-binding affinities and transcriptional activities. In addition, features of the ligand-induced receptor conformations were explored using a set of specific ER-binding peptides. The new 8-alkylnaringenins were found to span an activity spectrum ranging from full agonism to partial agonism to antagonism. Most strikingly, 8-(2,2-dimethylpropyl) naringenin exhibited full agonist character on ERR, but pronounced antagonist character on ER beta. Knowledge on how ER-subtype-selective activities can be designed provides valuable information for future drug or tool compound discovery.

  DOI：

  10.1021/jm060692n

文献信息

• Subtle Side-Chain Modifications of the Hop Phytoestrogen 8-Prenylnaringenin Result in Distinct Agonist/Antagonist Activity Profiles for Estrogen Receptors α and β
  作者：Frederik Roelens、Nina Heldring、Willem Dhooge、Martin Bengtsson、Frank Comhaire、Jan-Åke Gustafsson、Eckardt Treuter、Denis De Keukeleire

  DOI：10.1021/jm060692n

  日期：2006.12.1

  In search of therapeutic agents for estrogen-related pathologies, phytoestrogens are being extensively explored. In contrast to naringenin, 8-prenylnaringenin is a potent hop-derived estrogenic compound, highlighting the importance of the prenyl group for hormonal activity. We investigated the effects of substituting the prenyl group at C(8) with alkyl chains of varying lengths and branching patterns on estrogen receptor (ER) subtype ER alpha- and ER beta-binding affinities and transcriptional activities. In addition, features of the ligand-induced receptor conformations were explored using a set of specific ER-binding peptides. The new 8-alkylnaringenins were found to span an activity spectrum ranging from full agonism to partial agonism to antagonism. Most strikingly, 8-(2,2-dimethylpropyl) naringenin exhibited full agonist character on ERR, but pronounced antagonist character on ER beta. Knowledge on how ER-subtype-selective activities can be designed provides valuable information for future drug or tool compound discovery.
• 6,8-SUBSTITUTED NARINGENIN DERIVATIVE AND USE THEREOF
  申请人：SU Weiwei

  公开号：US20160130245A1

  公开（公告）日：2016-05-12

  Disclosed in the present invention are a 6,8-substituted naringenin derivative as shown in formula (I): in which A 6 and A 8 in formula (I) are respectively selected from H, halogen, hydroxyl, an alkyl group with 1-3 carbon atoms, and a straight-chain alkenyl, alcohol group, aldehyde group, or carboxylic acid group containing 2-3 carbon atoms, obtained by modifying naringenin as lead compound, or a pharmaceutically acceptable salt thereof, a preparation method therefor and use thereof in preparation of drugs for improving the function of the respiratory system and relieving cough.

  本发明公开了一种6,8-取代的柚皮素衍生物，如式（I）所示：其中，式（I）中的A6和A8分别选自H、卤素、羟基、含1-3个碳原子的烷基、直链烯基、醇基、醛基或含2-3个碳原子的羧酸基，通过对柚皮素进行改性而得到，或其药学上可接受的盐，其制备方法以及用于制备改善呼吸系统功能和缓解咳嗽药物的用途。