6-amino-7-hydroxycoumarin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-amino-7-hydroxycoumarin
• 英文别名: 6-Amino-7-hydroxychromen-2-one
• 化学式: C₉H₇NO₃
• 分子量: 177.159
• InChiKey: KVQWAVVIEKJSLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二(2-氯乙基)胺盐酸盐 、 6-amino-7-hydroxycoumarin 以 N-甲基吡咯烷酮 为溶剂， 反应 60.0h， 以65%的产率得到7-hydroxy-6-piperazin-1-ylchromen-2-one
  参考文献：
  名称：

  Dual 5-HT1A agonists and 5-HT re-uptake inhibitors by combination of indole-butyl-amine and chromenonyl-piperazine structural elements in a single molecular entity

  摘要：

  The dual serotonin (5-HT) re-uptake inhibitor and 5-HT1A receptor agonist vilazodone was found to increase central serotonin levels in rat brain. In the course of structural modifications of vilazodone 3-{4-[4-(2-oxo-2H-1-benzopyran-6-yl)-1-piperazinyl]-butyl}-1H-indole-5-carbonitrile 8i and its fluorine analogue 6-{4-[4-(5-fluor-3-indolyl)-butyl]-1-piperazinyl}-2H-1-benzopyran-2-one have been identified. These unsubstituted chromenones are equally potent at the 5-HT1A receptor and 5-HT transporter. The implementation of nitrogen functionalities in position 3 of the chromenones resulted in compounds acting as agonists at the 5-HT1A receptor and as 5-HT re-uptake inhibitors like vilazodone. Ex vivo 5-HT re-uptake inhibition and in vitro 5-HT agonism were determined in the PCA- and GTRgammaS-assay, respectively. The potential of these chromenones to increase central 5-HT levels was measured in microdialysis studies and especially the derivatives 3-{4-[4-(3-amino-2-oxo-2H-chromen-6-yl)-piperazin-1-yl]-butyl-1H-indole-5-carbonitrile 8f, ethyl (6-{4-[4-(5-cyano-1H-indol-3-yl)-butyl]-piperazin-1-yl}-2-oxo-2H-chromen-3-yl)-carbamate 8h and N-(6-{4-[4-(5-cyano-1H-indol-3-yl)-butyl]-piperazin-1-yl}-2-oxo-2H-chromen-3-yl)-acetamide 8k give rise to rapid development of increased serotonin levels in rat brain cortex, lasting longer than 3h. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.014
• 作为产物：
  描述：

  2H-1-苯并吡喃-2-酮,7-羟基-6-硝基- 在 palladium on activated charcoal 甲酸 、 三乙胺 作用下， 反应 0.33h， 以82%的产率得到6-amino-7-hydroxycoumarin
  参考文献：
  名称：

  Lin, Shaw-Tao; Yang, Fu-May; Yang, Heuy-Ju, Journal of Chemical Research - Part S, 1995, # 9, p. 372 - 373

  摘要：

  DOI：

文献信息

• Lin, Shaw-Tao; Yang, Fu-May; Yang, Heuy-Ju, Journal of Chemical Research - Part S, 1995, # 9, p. 372 - 373
  作者：Lin, Shaw-Tao、Yang, Fu-May、Yang, Heuy-Ju、Huang, Keh-Feng

  DOI：——

  日期：——
• 6-AMINO-1,2-BENZOPYRONES USEFUL FOR TREATMENT OF VIRAL DISEASES
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP0494231A1

  公开（公告）日：1992-07-15
• EP0494231A4
  申请人：——

  公开号：EP0494231A4

  公开（公告）日：1992-09-16
• [EN] 6-AMINO-1,2-BENZOPYRONES USEFUL FOR TREATMENT OF VIRAL DISEASES
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：WO1991004663A1

  公开（公告）日：1991-04-18

  (EN) Unsubstituted or substituted 6-amino-1,2-benzopyrones are potent, selective and non-toxic inhibitors and suppressants of viral infections in a mammalian host. The compounds are particularly useful for treatment of AIDS, herpetic episodes and cytomegaloviral infections. The method of treatment of viral diseases by 6-amino-1,2-benzopyrones is described.(FR) On décrit des 6-amino-1,2-benzopyrones substitués ou non qui sont des inhibiteurs puissants, sélectifs et non toxiques et des suppressants d'infections virales présentes dans un hôte mammifère. Les composés sont particulièrement utiles pour le traitement du SIDA, des épisodes herpétiques, et des infections cytomégalovirales. On décrit également le procédé de traitement des maladies virales utilisant des 6-amino-1,2-benzopyrones.
• Dual 5-HT1A agonists and 5-HT re-uptake inhibitors by combination of indole-butyl-amine and chromenonyl-piperazine structural elements in a single molecular entity
  作者：Timo Heinrich、Henning Böttcher、Kai Schiemann、Günter Hölzemann、Michael Schwarz、Gerd D. Bartoszyk、Christoph van Amsterdam、Hartmut E. Greiner、Christoph A. Seyfried

  DOI：10.1016/j.bmc.2004.07.014

  日期：2004.9

  The dual serotonin (5-HT) re-uptake inhibitor and 5-HT1A receptor agonist vilazodone was found to increase central serotonin levels in rat brain. In the course of structural modifications of vilazodone 3-4-[4-(2-oxo-2H-1-benzopyran-6-yl)-1-piperazinyl]-butyl}-1H-indole-5-carbonitrile 8i and its fluorine analogue 6-4-[4-(5-fluor-3-indolyl)-butyl]-1-piperazinyl}-2H-1-benzopyran-2-one have been identified. These unsubstituted chromenones are equally potent at the 5-HT1A receptor and 5-HT transporter. The implementation of nitrogen functionalities in position 3 of the chromenones resulted in compounds acting as agonists at the 5-HT1A receptor and as 5-HT re-uptake inhibitors like vilazodone. Ex vivo 5-HT re-uptake inhibition and in vitro 5-HT agonism were determined in the PCA- and GTRgammaS-assay, respectively. The potential of these chromenones to increase central 5-HT levels was measured in microdialysis studies and especially the derivatives 3-4-[4-(3-amino-2-oxo-2H-chromen-6-yl)-piperazin-1-yl]-butyl-1H-indole-5-carbonitrile 8f, ethyl (6-4-[4-(5-cyano-1H-indol-3-yl)-butyl]-piperazin-1-yl}-2-oxo-2H-chromen-3-yl)-carbamate 8h and N-(6-4-[4-(5-cyano-1H-indol-3-yl)-butyl]-piperazin-1-yl}-2-oxo-2H-chromen-3-yl)-acetamide 8k give rise to rapid development of increased serotonin levels in rat brain cortex, lasting longer than 3h. (C) 2004 Elsevier Ltd. All rights reserved.