6-methylcoumarin-3-N-p-tolylcarbamide | 38485-84-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-methylcoumarin-3-N-p-tolylcarbamide
• 英文别名: N-(4-tolyl)-6-methyl-2-oxo-2H-1-benzopyran-3-carboxamide；6-methyl-N-(4-methylphenyl)-2-oxo-2H-chromene-3-carboxamide；6-methyl-N-(4-methylphenyl)-2-oxochromene-3-carboxamide
• CAS: 38485-84-6
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: MFUWDBLYKLNULI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 6-methyl-2-oxo-2H-chromene-3-carboxylate 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 6-methylcoumarin-3-N-p-tolylcarbamide
  参考文献：
  名称：

  Exploring coumarin potentialities: development of new enzymatic inhibitors based on the 6-methyl-3-carboxamidocoumarin scaffold

  摘要：

  新型6-甲基-3-羧胺基香豆素经过有效的三步合成策略合成，并对MAO、AChE和BuChE酶进行了筛选。

  DOI：

  10.1039/c6ra05262b

文献信息

• Coumarins and adenosine receptors: New perceptions in structure-affinity relationships
  作者：André Fonseca、Maria João Matos、Santiago Vilar、Sonja Kachler、Karl-Norbert Klotz、Eugenio Uriarte、Fernanda Borges

  DOI：10.1111/cbdd.13075

  日期：2018.1

  Adenosine receptor (AR) subtypes are involved in several physiological and pharmacological processes. Ligands that are able to selectively modulate one receptor subtype can delay or slow down the progression of diverse diseases. In this context, our research group focused its investigation into the discovery and development of novel, potent and selective AR ligands based on coumarin scaffold. Therefore

  腺苷受体（AR）亚型涉及几种生理和药理过程。能够选择性调节一种受体亚型的配体可以延缓或减缓多种疾病的发展。在这种情况下，我们的研究小组将研究重点放在了基于香豆素骨架的新型，有效和选择性AR配体的发现和开发上。因此，一系列的3-phenylcarboxamidocoumarins合成以及它们在人AR亚型的亲和性是通过放射性配体结合测定法用于筛选阿1，A 2A和A 3个受体和对于A 2B由腺苷酸环化酶测定。发现化合物26最显着，其h A1 / ħ甲3和ħ甲2A / ħ甲3选择性的42，为A 3 AR（ķ我 = 2.4μ米）。受体驱动的分子建模研究为化合物26的结合/选择性数据以及随后的优化过程提供了有价值的信息。此外，化合物26根据与该概念有关的一般指导原则表现出药物样性质。
• Novel 3-Carboxamide-coumarins as Potent and Selective FXIIa Inhibitors
  作者：Séverine Robert、Carine Bertolla、Bernard Masereel、Jean-Michel Dogné、Lionel Pochet

  DOI：10.1021/jm8002697

  日期：2008.6.1

  Recently, FXIIa was highlighted as an original attractive target for the development of new anticoagulant drugs with low rates of therapy-related hemorrhages. In this work, we describe the development of a new series of 3-carboxamide-coumarins that are the first potent and selective nonpeptidic inhibitors of FXIIa.
• Coumarin versus Chromone Monoamine Oxidase B Inhibitors: Quo Vadis?
  作者：André Fonseca、Joana Reis、Tiago Silva、Maria João Matos、Donatella Bagetta、Francesco Ortuso、Stefano Alcaro、Eugenio Uriarte、Fernanda Borges

  DOI：10.1021/acs.jmedchem.7b00918

  日期：2017.8.24

  Because of the lack of significant disease-modifying drugs for neurodegenerative disorders, a pressing need for new chemical entities endowed with IMAO-B still exists. Within this framework, and for the first time, a study was performed to compare coumarin- and chomone-3-phenylcarboxamide scaffolds. Compounds 10a and 10b were the most potent, selective, and reversible noncompetitive IMAO-B. The benzopyrone sp(2) oxygen atom was found to be position independent and a productive contributor for the ligand-enzyme complex stability.
• Elkasaby, M. A.; Noureldin, N. A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 12, p. 1080 - 1081
  作者：Elkasaby, M. A.、Noureldin, N. A.

  DOI：——

  日期：——