N-(4-methoxyphenyl)-4-oxo-4H-chromen-3-carboxamide | 1268279-37-3

• 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: N-(4-methoxyphenyl)-4-oxo-4H-chromen-3-carboxamide
• 英文别名: N-(4-methoxyphenyl)-4-oxo-4H-1-benzopyran-3-carboxamide；N-(4-methoxyphenyl)-4-oxo-4H-chromene-3-carboxamide；N-(4-methoxyphenyl)-4-oxochromene-3-carboxamide
• CAS: 1268279-37-3
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: XPWNDBXEISTXEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-丙烯-1-酮,3-(二甲氨基)-1-(2-羟基苯基)- 、 对甲氧基苯异氰酸酯 以 甲苯 为溶剂， 以50%的产率得到N-(4-methoxyphenyl)-4-oxo-4H-chromen-3-carboxamide
  参考文献：
  名称：

  从 2-羟基芳基氨基烯酮和异氰酸酯合成 3-(N-芳基氨基甲酰基)色酮

  摘要：

  通过 3-二甲氨基-1-(2-羟基芳基)prop-2-en-1-ones 与芳基异氰酸酯反应合成 2-未取代和 2-取代的 3-(N-芳基氨基甲酰基)-色酮的新方法具有被提议。

  DOI：

  10.1007/s11172-019-2423-5

文献信息

• Discovery of novel A3 adenosine receptor ligands based on chromone scaffold
  作者：Alexandra Gaspar、Joana Reis、Sonja Kachler、Silvia Paoletta、Eugenio Uriarte、Karl-Norbert Klotz、Stefano Moro、Fernanda Borges

  DOI：10.1016/j.bcp.2012.03.007

  日期：2012.7

  has been developed. Accordingly, two series of novel chromone carboxamides placed at positions C2 (compounds 2-13) and C3 (compounds 15-26) of the gamma-pyrone ring were synthesized using chromone carboxylic acids (compounds 1 or 14) as starting materials. From this study and on the basis of the obtained structure-activity relationships it was concluded that the chromone carboxamide scaffold represent

  已经开发了一个致力于发现新化学实体（NCE）作为AR配体的项目，该配体包含苯并-γ-吡喃酮[（4H）-1-苯并吡喃-4-酮]子结构。因此，使用色酮羧酸（化合物1或14）作为起始原料，合成了位于γ-吡喃酮环的位置C2（化合物2-13）和C3（化合物15-26）的两个新的色酮羧酰胺系列。从这项研究中，并在获得的结构-活性关系的基础上，得出的结论是，色酮羧酰胺支架代表了一类新型的AR配体。最显着的色酮是对A3AR表现出更好亲和力的化合物21和26（分别为Ki = 3680 nM和Ki = 3750 nM）。受体驱动的分子建模研究提供了有关色酮的结合/选择性数据的信息。
• Chromone 3-phenylcarboxamides as potent and selective MAO-B inhibitors
  作者：Alexandra Gaspar、Joana Reis、André Fonseca、Nuno Milhazes、Dolores Viña、Eugenio Uriarte、Fernanda Borges

  DOI：10.1016/j.bmcl.2010.11.128

  日期：2011.1

  Monoamine oxidase (MAO) is an enzyme, present in mammals in two isoforms MAO-A and MAO-B. These isoforms have a crucial role in neurotransmitters metabolism, representing an attractive drug target in the therapy of neurodegenerative diseases (MAO-B) and depression (MAO-A). In this context, our work has been focused on the discovery of new chemical entities (NCEs) for MAO inhibition, based on the development of chromone carboxamides. Chromone derivatives with a carboxamide function located in position 2- and 3- of the benzo-gamma-pyrone core, (compounds 2-6 and 8-12) were synthesized, with moderate/good yields, by a one-pot condensation reaction using phosphonium salts as coupling reagents. The synthetic compounds were screened towards human MAO isoforms (hMAO) to evaluate their potency and selectivity. The chromone-3-carboxamides show high selectivity to hMAO-B, with compounds 9 and 12 displaying IC50 values at nanomolar range. (C) 2010 Published by Elsevier Ltd.
• Synthesis of 3-(N-arylcarbamoyl)chromones from 2-hydroxyarylaminoenones and isocyanates
  作者：K. A. Myannik、I. S. Semenova、V. N. Yarovenko、M. M. Krayushkin

  DOI：10.1007/s11172-019-2423-5

  日期：2019.1

  A new method for the synthesis of 2-unsubstituted and 2-substituted 3-(N-arylcarbamoyl)-chromones by the reaction of 3-dimethylamino-1-(2-hydroxyaryl)prop-2-en-1-ones with arylisocyanates has been proposed.

  通过 3-二甲氨基-1-(2-羟基芳基)prop-2-en-1-ones 与芳基异氰酸酯反应合成 2-未取代和 2-取代的 3-(N-芳基氨基甲酰基)-色酮的新方法具有被提议。