6,7-dimethoxy-3-methyl-2H-chromen-2-one | 86818-97-5

• 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: 6,7-dimethoxy-3-methyl-2H-chromen-2-one
• 英文别名: 6,7-dimethoxy-3-methylchromen-2-one
• CAS: 86818-97-5
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: OCJKIFTZIZNILV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-3-methyl-2H-chromen-2-one 在 N-溴代丁二酰亚胺(NBS) 、 sodium methylate 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 7.5h， 生成 6,7-Dimethoxy-3-[(2-nitroimidazol-1-yl)methyl]chromen-2-one
  参考文献：
  名称：

  Fluorescent markers for hypoxic cells: a study of nitroaromatic compounds, with fluorescent heterocyclic side chains, that undergo bioreductive binding

  摘要：

  Several novel compounds having both a 2-nitroimidazole nucleus and a fluorescent ring system in their molecular structure were prepared and evaluated as potential fluorescent probes for hypoxia. Bioreduction of nitroimidazoles, which is inhibited by oxygen, is known to lead to binding of bioreductive metabolites to cellular macromolecules and this provides a mechanism for binding the fluorescent moiety to hypoxic cells. These compounds can incorporate a wide range of fluorophors and can therefore be designed to suit the laser-line wavelengths available for excitation of fluorescence in the flow cytometer. Several nitroimidazoles with naphthalimide side chains were rapidly taken up into cells and became concentrated in the cells, thus reducing their concentration in the extracellular medium. This suggests a potential microscopic bioavailability problem with probes of this type when used in vivo as they would become progressively depleted in the extracellular fluid as they diffused from blood vessels, through layers of packed cells in tumors, to the hypoxic cells where they could undergo hypoxia-specific metabolism. Synthesis of nitroimidazoles with coumarin fluorophors led to several potentially useful probes for hypoxia; substituents on the coumarin fluorophor had a marked effect on the cellular fluorescence of these compounds.

  DOI：

  10.1021/jm00111a049
• 作为产物：
  描述：

  3,4-二甲氧基苯酚 在 三乙胺 、 magnesium chloride 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 40.0h， 生成 6,7-dimethoxy-3-methyl-2H-chromen-2-one
  参考文献：
  名称：

  7-叠氮基-3-甲酰基香豆素的合成-生物正交适用的荧光染料合成中的关键前体

  摘要：

  香豆素代表着重要的天然产物，是各种药物和荧光染料的共同组成部分。在本文中，我们介绍了香豆素的合成，该香豆素可以用作生物正交适用的荧光染料的设计和合成中的关键起始材料。7-叠氮基-3-甲酰基香豆素的合成从7-二烯丙基氨基香豆素开始。该烯丙基保护的氨基香豆素原本很难通过常规方法获得，但可以通过连续的Wittig反应-UV异构化工艺以高收率方便地获得。对该顺序方法进行了更详细的研究，并将其应用于即使在一个锅中也可以合成一系列取代的香豆素。

  DOI：

  10.1002/jhet.3151

文献信息

• Searching for Multi-Targeting Neurotherapeutics against Alzheimer’s: Discovery of Potent AChE-MAO B Inhibitors through the Decoration of the 2H-Chromen-2-one Structural Motif
  作者：Leonardo Pisani、Roberta Farina、Ramon Soto-Otero、Nunzio Denora、Giuseppe Mangiatordi、Orazio Nicolotti、Estefania Mendez-Alvarez、Cosimo Altomare、Marco Catto、Angelo Carotti

  DOI：10.3390/molecules21030362

  日期：——

  vitro inhibitory activities against MAO-B. Within this series, derivative 3h emerged as the most interesting hit compound, being a moderate AChE inhibitor (IC50 = 8.99 µM) and a potent and selective MAO-B inhibitor (IC50 = 2.8 nM). Preliminary studies in human neuroblastoma SH-SY5Y cell lines demonstrated its low cytotoxicity and disclosed a promising neuroprotective effect at low doses (0.1 µM) under oxidative

  对开发针对神经退行性综合症，尤其是阿尔茨海默氏病（AD）的真正的疾病缓解药物的需求，使研究转向可靠的药物发现策略，以揭示具有比单靶标药物更高的治疗功效的临床候选药物。通过遵循多目标方法，我们设计和合成了新型的双乙酰胆碱酯酶（AChE）-单胺氧化酶B（MAO-B）抑制剂，通过装饰2H-chromen-2-one骨架。在位置3带有炔丙基胺部分的化合物在体外对MAO-B表现出最高的抑制活性。在该系列中，衍生物3h成为最有趣的命中化合物，是中度AChE抑制剂（IC50 = 8.99 µM）和有效且选择性的MAO-B抑制剂（IC50 = 2.8 nM）。对人类神经母细胞瘤SH-SY5Y细胞系的初步研究表明，它具有较低的细胞毒性，并揭示了在两种线粒体毒素（寡霉素-A和鱼藤酮）促进的氧化应激条件下，低剂量（0.1 µM）下有希望的神经保护作用。在基于Madin-Darby犬肾（MDCK）II-MDR1细
• Cingolani et al., Gazzetta Chimica Italiana, 1953, vol. 83, p. 647,651
  作者：Cingolani et al.

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• Mali, R. S.; Yeola, Suresh N.; Kulkarni, B. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 4, p. 352 - 354
  作者：Mali, R. S.、Yeola, Suresh N.、Kulkarni, B. K.

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• HODGKISS, RICHARD J.;JONES, GARETH W.;LONG, ANTHONY;MIDDLETON, RICHARD W.+, J. MED. CHEM., 34,(1991) N, C. 2268-2274
  作者：HODGKISS, RICHARD J.、JONES, GARETH W.、LONG, ANTHONY、MIDDLETON, RICHARD W.+

  DOI：——

  日期：——
• MALI, R. S.;YEOLA, SURESH, N.;KULKARNI, B. K., INDIAN J. CHEM., 1983, 22, N 4, 352-354
  作者：MALI, R. S.、YEOLA, SURESH, N.、KULKARNI, B. K.

  DOI：——

  日期：——