7-(6-bromohexyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one | 188881-57-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-(6-bromohexyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one
• 英文别名: 7-O-(6-bromohexyl)-daidzein；7-(6-Bromo-hexyloxy)-3-(4-hydroxy-phenyl)-chromen-4-one；7-(6-bromohexoxy)-3-(4-hydroxyphenyl)chromen-4-one
• CAS: 188881-57-4
• 化学式: C₂₁H₂₁BrO₄
• 分子量: 417.299
• InChiKey: GSUQEVUSISXFAN-UHFFFAOYSA-N

物化性质

• 熔点：
  140-142 °C
• 沸点：
  581.1±50.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  7-(6-bromohexyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one 在 氨 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 7-O-(6-aminohexyl)-daidzein
  参考文献：
  名称：

  Daidzin derivatives for the treatment of alcohol dependence or alcohol abuse

  摘要：

  揭示了一种利用二氧化和类似于二氧化的化合物治疗酒精滥用的方法。还公开了一种筛选具有抗酒精依赖活性的化合物的方法。

  公开号：

  EP1645272A3
• 作为产物：
  描述：

  4'-O-acetyldaidzein 在 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 7-(6-bromohexyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  类胡萝卜素-黄酮结合物的合成、抗氧化性能及自组装研究

  摘要：

  类黄酮和类胡萝卜素具有有益的生理作用，例如高抗氧化能力、抗癌、免疫调节和抗炎特性，以及对紫外线的保护作用。实现了疏水性类胡萝卜素与亲水性黄酮类化合物（例如大豆黄酮和白杨素）的共价偶联，产生了新的两亲结构。黄豆苷元和白杨素的 7-叠氮己基醚通过五个步骤制备，并且它们的叠氮-炔[4+2]环加成与 8'-apo-β-胡萝卜素、玉米黄质和辣椒红的戊烯酸盐发生类胡萝卜素-类黄酮缀合物。对ABTS•+自由基阳离子的抗氧化能力和最终产品的自组装进行了检测。 1:1 类黄酮-类胡萝卜素杂合体通常表现出比其母体类黄酮更高的抗氧化活性，但低于相应的类胡萝卜素。然而，人们发现玉米黄质和辣椒红的二黄酮混合物在抗氧化能力方面表现出协同增强作用。玉米黄质-类黄酮缀合物的 ECD（电子圆二色性）和 UV-vis 分析表明，根据所用非质子极性溶剂的溶剂比例和类型，它们在丙酮/水和四氢呋喃/水混合物中形成不同的光学活性 J

  DOI：

  10.3390/molecules25030636

文献信息

• The Mitochondrial Monoamine Oxidase−Aldehyde Dehydrogenase Pathway:  A Potential Site of Action of Daidzin
  作者：Nadège Rooke、Dian-Jun Li、Junqing Li、Wing Ming Keung

  DOI：10.1021/jm990614i

  日期：2000.11.1

  Recent studies showed that daidzin suppresses ethanol intake in ethanol-preferring laboratory animals. In vitro, it potently and selectively inhibits the mitochondrial aldehyde dehydrogenase (ALDH-2). Further, it inhibits the conversion of monoamines such as serotonin (5-HT) and dopamine (DA) into their respective acid metabolites, 5-hydroxyindole-3-acetic acid (5-HIAA) and 3,4-dihydroxyphenylacetic acid (DOPAC) in isolated hamster or rat liver mitochondria. Studies on the suppression of ethanol intake and inhibition of 5-HIAA (or DOPAC) formation by six structural analogues of daidzin suggested a potential link between these two activities. This, together with the finding that daidzin does not affect the rates of mitochondria-catalyzed oxidative deamination of these monoamines, raised the possibility that the ethanol intake-suppressive (antidipsotropic) action of daidzin is not mediated by the monoamines but rather by their reactive biogenic aldehyde intermediates such as 5-hydroxyindole-3-acetaldehyde (5-HIAL) and/or 3,4-dihydroxyphenylacetaldehyde (DOPAL) which accumulate in the presence of daidzin. To further evaluate this possibility, we synthesized more structural analogues of daidzin and tested and compared their antidipsotropic activities in Syrian golden hamsters with their effects on monoamine metabolism in isolated hamster liver mitochondria using 5-HT as the substrate. Effects of daidzin and its structural analogues on the activities of monoamine oxidase (MAO) and ALDH-2, the key enzymes involved in 5-HT metabolism in the mitochondria, were also examined. Results from these studies reveal a positive correlation between the antidipsotropic activities of these analogues and their abilities to increase 5-HIAL, accumulation during 5-HT metabolism in isolated hamster liver mitochondria. Daidzin analogues that potently inhibit ALDH-2 but have no or little effect on MAO are most antidipsotropic, whereas those that also potently inhibit MAO exhibit little, if any, antidipsotropic activity. These results, although inconclusive, are consistent with the hypothesis that daidzin may act via the mitochondrial MAO/ALDH pathway and that a biogenic aldehyde such as 5-HIAL may be important in mediating its antidipsotropic action.
• METHODS AND ASSAYS USEFUL IN THE TREATMENT OF ALCOHOL DEPENDENCE OR ALCOHOL ABUSE
  申请人：THE ENDOWMENT FOR RESEARCH IN HUMAN BIOLOGY, INC.

  公开号：EP1077697A1

  公开（公告）日：2001-02-28
• US6121010A
  申请人：——

  公开号：US6121010A

  公开（公告）日：2000-09-19
• [EN] METHODS AND ASSAYS USEFUL IN THE TREATMENT OF ALCOHOL DEPENDENCE OR ALCOHOL ABUSE<br/>[FR] PROCEDES ET METHODES DE CRIBLAGE UTILES POUR TRAITER LA DEPENDANCE A L'ALCOOL OU L'ABUS D'ALCOOL
  申请人：THE ENDOWMENT FOR RESEARCH IN HUMAN BIOLOGY, INC.

  公开号：WO1999058124A1

  公开（公告）日：1999-11-18

  (EN) A method for the treatment of alcohol abuse using diadzin and compounds analogous to diadzin is disclosed. Also disclosed is a method for screening compounds having antidipsotropic activity.(FR) L'invention concerne un procédé servant à traiter l'abus d'alcool au moyen de daidzine et de composés analogues à daidzine. Elle concerne également une méthode de criblage de composés exerçant une activité antidipsotropique.
• Study on the Synthesis, Antioxidant Properties, and Self-Assembly of Carotenoid–Flavonoid Conjugates
  作者：Ildikó Línzembold、Dalma Czett、Katalin Böddi、Tibor Kurtán、Sándor Balázs Király、Gergely Gulyás-Fekete、Anikó Takátsy、Tamás Lóránd、József Deli、Attila Agócs、Veronika Nagy

  DOI：10.3390/molecules25030636

  日期：——

  capsanthin afforded carotenoid–flavonoid conjugates. The trolox-equivalent antioxidant capacity against ABTS•+ radical cation and self-assembly of the final products were examined. The 1:1 flavonoid–carotenoid hybrids generally showed higher antioxidant activity than their parent flavonoids but lower than that of the corresponding carotenoids. The diflavonoid hybrids of zeaxanthin and capsanthin, however

  类黄酮和类胡萝卜素具有有益的生理作用，例如高抗氧化能力、抗癌、免疫调节和抗炎特性，以及对紫外线的保护作用。实现了疏水性类胡萝卜素与亲水性黄酮类化合物（例如大豆黄酮和白杨素）的共价偶联，产生了新的两亲结构。黄豆苷元和白杨素的 7-叠氮己基醚通过五个步骤制备，并且它们的叠氮-炔[4+2]环加成与 8'-apo-β-胡萝卜素、玉米黄质和辣椒红的戊烯酸盐发生类胡萝卜素-类黄酮缀合物。对ABTS•+自由基阳离子的抗氧化能力和最终产品的自组装进行了检测。 1:1 类黄酮-类胡萝卜素杂合体通常表现出比其母体类黄酮更高的抗氧化活性，但低于相应的类胡萝卜素。然而，人们发现玉米黄质和辣椒红的二黄酮混合物在抗氧化能力方面表现出协同增强作用。玉米黄质-类黄酮缀合物的 ECD（电子圆二色性）和 UV-vis 分析表明，根据所用非质子极性溶剂的溶剂比例和类型，它们在丙酮/水和四氢呋喃/水混合物中形成不同的光学活性 J