8-allylnaringenin | 1134396-63-6

• 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-allylnaringenin
• 英文别名: (+/-)-4',5,7-trihydroxy-8-allyl-flavanone；5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-prop-2-enyl-2,3-dihydrochromen-4-one
• CAS: 1134396-63-6
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: CNFQLHJIXXOQPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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-allylnaringenin 在 sodium chlorite 、 氨基磺酸 、 臭氧 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 2.75h， 生成 6-chloro-naringenin-8-acetic acid
  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：

  (+/-)-4',5,7-trimethoxymethoxy-8-allyl-flavanone 在 盐酸 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.75h， 以68%的产率得到8-allylnaringenin
  参考文献：
  名称：

  Synthesis, biological evaluation and quantitative structure-activities relationship of flavonoids as vasorelaxant agents

  摘要：

  A series of flavonoid derivatives were designed, synthesized. Their vasorelaxant activities were evaluated experimentally against rat aorta rings pretreated with phenylephrine (PE). Among them, 6-hydroxy-8-allyl- 4'-chloro-flavanone 8q exhibited the highest vasodilatory activity (EC50 = 4.6 mu M, E-max = 95.1%). The 3D-QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method, and a statistically reliable model with good predictive power (r(2) = 0.872 and q(cv)(2) = 0.496) was established. The contour plots of CoMFA model provide a good insight into the structure-activity relationships of these compounds and may be used to design more potent flavonoids derivatives as vasorelaxant agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.052

文献信息

• ISOGENIC HUMAN CELL LINES COMPRISING MUTATED CANCER ALLELES AND PROCESS USING THE CELL LINES
  申请人：Bardelli Alberto

  公开号：US20120115896A1

  公开（公告）日：2012-05-10

  Isogenic human cell lines comprising at least one mutated cancer allele under the control of the cell line endogenous promoter, which corresponds to the wild-type cancer allele promoter are disclosed, as well as an in vitro process for determining sensitivity/resistance of a patient suffering from a tumor to a pharmacological agent comprising the following steps: a) identifying at least one mutated cancer allele in a tissue affected by a tumor of said patient; b) providing an isogenic human cell line representative of the tissue, wherein the cell line comprises at least the identified mutated cancer allele, which is under the control of the cell line endogenous promoter corresponding to the wild-type cancer allele promoter; c) putting in contact said cell line with the pharmacological agent; d) determining a variation of proliferation, apoptosis or cytotoxicity of the cell line in presence of the pharmacological agent; wherein the variation of proliferation, apoptosis car cytotoxicity indicative of the sensitivity/resistance of the patient tumor to the pharmacological agent.
• [EN] NARINGENIN DERIVATIVES WITH SELECTIVITY ON ERS<br/>[FR] DERIVES DE NARINGENINE PRESENTANT UNE SELECTIVITE SUR DES ERS
  申请人：UNIV GENT

  公开号：WO2007053915A2

  公开（公告）日：2007-05-18

  [EN] The present invention relates to naringenin derivatives with selective anti¬ estrogenic activity and their use in the treatment of diseases or disorders estrogen- deficiency dependent disorders, diseases with excessive estrogen production or conditions benefiting from modulated estrogen production.
  [FR] L'invention concerne des dérivés de naringénine à activité anti-oestrogène sélective, et leur utilisation dans le traitement de maladies ou de troubles liés à des déficiences en oestrogène, de maladies à production excessive en oestrogène, ou d'états résultant d'une production d'oestrogène modulée.
• Synthesis, biological evaluation and quantitative structure-activities relationship of flavonoids as vasorelaxant agents
  作者：Xiaowu Dong、Tao Liu、Jingying Yan、Peng Wu、Jing Chen、Yongzhou Hu

  DOI：10.1016/j.bmc.2008.11.052

  日期：2009.1

  A series of flavonoid derivatives were designed, synthesized. Their vasorelaxant activities were evaluated experimentally against rat aorta rings pretreated with phenylephrine (PE). Among them, 6-hydroxy-8-allyl- 4'-chloro-flavanone 8q exhibited the highest vasodilatory activity (EC50 = 4.6 mu M, E-max = 95.1%). The 3D-QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method, and a statistically reliable model with good predictive power (r(2) = 0.872 and q(cv)(2) = 0.496) was established. The contour plots of CoMFA model provide a good insight into the structure-activity relationships of these compounds and may be used to design more potent flavonoids derivatives as vasorelaxant agents. (C) 2008 Elsevier Ltd. All rights reserved.
• 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。