3-hydroxy-6-methoxy-2H-chromen-2-one | 3450-77-9

• 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: 3-hydroxy-6-methoxy-2H-chromen-2-one
• 英文别名: 3-Hydroxy-6-methoxy-cumarin；3-hydroxy-6-methoxy-chromen-2-one；Hydroxyl-6-methoxycoumarin；3-hydroxy-6-methoxychromen-2-one
• CAS: 3450-77-9
• 化学式: C₁₀H₈O₄
• 分子量: 192.171
• InChiKey: JCRCMXRVNODTHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  3-hydroxy-6-methoxy-2H-chromen-2-one 在 camphor-10-sulfonic acid 、 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 42.0h， 生成 9-methoxy-1-methylchromeno[3,4-b]pyridin-5-one
  参考文献：
  名称：

  Pavé, Grégoire; Chalard, Pierre; Viaud-Massuard, Marie-Claude, Synlett, 2003, # 7, p. 987 - 990

  摘要：

  DOI：
• 作为产物：
  描述：

  6-methoxy-3-aminocoumarin 在 盐酸 作用下， 生成 3-hydroxy-6-methoxy-2H-chromen-2-one
  参考文献：
  名称：

  Pavé, Grégoire; Chalard, Pierre; Viaud-Massuard, Marie-Claude, Synlett, 2003, # 7, p. 987 - 990

  摘要：

  DOI：

文献信息

• A novel class of human 15-LOX-1 inhibitors based on 3-hydroxycoumarin
  作者：Seyed Jamal Alavi、Hamid Sadeghian、Seyed Mohammad Seyedi、Alireza Salimi、Hossein Eshghi

  DOI：10.1111/cbdd.13174

  日期：2018.6

  Owing to the importance of these enzymes, mechanistic studies, product analysis, and synthesis of inhibitors have expanded. In this study, a series of hydroxycoumarins, methoxy‐3‐hydroxy coumarins, and 7‐alkoxy‐3‐hydroxy coumarins were synthesized and evaluated as potential inhibitors of human 15‐LOX‐1. Among the synthetic coumarins, 7‐methoxy‐3‐hydroxycoumarin derivative demonstrated potent inhibitory

  哺乳动物的炎症，敏感性和某些癌症与脂氧合酶的活性密切相关。由于这些酶的重要性，机理研究，产物分析和抑制剂的合成得到了扩展。在这项研究中，合成了一系列羟基香豆素，甲氧基-3-羟基香豆素和7-烷氧基-3-羟基香豆素，并将其评估为人类15-LOX-1的潜在抑制剂。在合成香豆素中，7-甲氧基-3-羟基香豆素衍生物显示出有效的抑制活性，化合物5f显示出最佳的抑制效果。自由基清除评估，IC 50，HNMR和DPPH漂白结果表明，电子性能是合成香豆素抑制脂加氧酶效能的主要因素。根据理论研究，有人提出苯环第七位取代基的介观效应是氧自由基中间体稳定性的主要因素之一。
• [EN] INHIBITORS OF CATECHOL O-METHYL TRANSFERASE AND THEIR USE IN THE TREATMENT OF PSYCHOTIC DISORDERS<br/>[FR] INHIBITEURS DE CATÉCHOL O-MÉTHYL TRANSFÉRASE ET UTILISATION ASSOCIÉE DANS LE TRAITEMENT DE TROUBLES PSYCHOTIQUES
  申请人：MERCK SHARP & DOHME

  公开号：WO2011109254A1

  公开（公告）日：2011-09-09

  The present invention relates to 4-pyridinone compounds which are inhibitors of catechol O-methyltransferase (COMT), and are useful in the treatment and prevention of neurological and psychiatric disorders and diseases in which COMT enzyme is involved. The present invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which COMT is involved.

  本发明涉及4-吡啶酮化合物，它们是儿茶酚-O-甲基转移酶(COMT)的抑制剂，并且在涉及COMT酶的神经和精神疾病和疾病的治疗和预防中有用。本发明还涉及包含这些化合物的药物组合物以及在涉及COMT的这些疾病的预防或治疗中使用这些化合物和组合物。
• Reaction of aryl-2-hydroxypropenoic derivatives with boron tribromide
  作者：Romain Dupont、Philippe Cotelle

  DOI：10.1016/s0040-4039(00)02011-6

  日期：2001.1

  trimethoxyphenyl-2-hydroxypropenoic acids 1a–d gave mixtures of (E) and (Z) mono, di or trihydroxyphenyl-2-hydroxypropenoic acids 2a–d when treated with boron tribromide. The isomerisation proceeds during the work-up and depends on the duration of the hydrolysis and the number of oxygens on the aromatic ring. When the aromatic ring was substituted with a methoxy group at the ortho position, a cyclisation occurs

  （Ž） -单，二或三甲氧基苯基-2- hydroxypropenoic酸1A-d得到（的混合物ë）和（Ž）单，二或三羟基苯基-2- hydroxypropenoic酸图2a-d时用三溴化硼。异构化在后处理过程中进行，并取决于水解的持续时间和芳环上的氧数。当芳环在邻位被甲氧基取代时，发生环化，并且可以获得3-羟基香豆素3和苯并呋喃-2-羧酸4。3-羟基香豆素3a 3-（2-甲氧基苯基）-2，3-环氧丙酸甲酯与三溴化硼的反应也几乎可以定量获得。
• Design, synthesis and biological evaluation of coumarin alkylamines as potent and selective dual binding site inhibitors of acetylcholinesterase
  作者：Marco Catto、Leonardo Pisani、Francesco Leonetti、Orazio Nicolotti、Paolo Pesce、Angela Stefanachi、Saverio Cellamare、Angelo Carotti

  DOI：10.1016/j.bmc.2012.10.045

  日期：2013.1

  Acetylcholinesterase inhibitors (AChEIs) are currently the drugs of choice, although only symptomatic and palliative, for the treatment of Alzheimer's disease (AD). Donepezil is one of most used AChEIs in AD therapy, acting as a dual binding site, reversible inhibitor of AChE with high selectivity over butyrylcholinesterase (BChE). Through a combined target-and ligand-based approach, a series of coumarin alkylamines matching the structural determinants of donepezil were designed and prepared. 6,7-Dimethoxycoumarin derivatives carrying a protonatable benzylamino group, linked to position 3 by suitable linkers, exhibited fairly good AChE inhibitory activity and a high selectivity over BChE. The inhibitory potency was strongly influenced by the length and shape of the spacer and by the methoxy substituents on the coumarin scaffold. The inhibition mechanism, assessed for the most active compound 13 (IC50 7.6 nM) resulted in a mixed-type, thus confirming its binding at both the catalytic and peripheral binding sites of AChE. (C) 2012 Elsevier Ltd. All rights reserved.
• INHIBITORS OF CATECHOL O-METHYL TRANSFERASE AND THEIR USE IN THE TREATMENT OF PSYCHOTIC DISORDERS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2542076A1

  公开（公告）日：2013-01-09