2-(1H-1,2,4-triazol-1-yl)-4H-1-benzopyran-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(1H-1,2,4-triazol-1-yl)-4H-1-benzopyran-4-one
• 英文别名: 2-(1,2,4-Triazol-1-yl)chromen-4-one
• 化学式: C₁₁H₇N₃O₂
• 分子量: 213.195
• InChiKey: DKTARSLICHAGFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吗啉 、 2-(1H-1,2,4-triazol-1-yl)-4H-1-benzopyran-4-one 以 N,N-二甲基甲酰胺 为溶剂， 以71%的产率得到2-(4-morpholinyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Oxidative regioselective amination of chromones exposes potent inhibitors of the hedgehog signaling pathway

  摘要：

  一种新型的选择性偶联方法，用于合成具有生物活性的化合物，将环酮与唑类化合物结合。

  DOI：

  10.1039/c4cc08376h
• 作为产物：
  描述：

  1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone 在 吡啶 、 碘 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-(1H-1,2,4-triazol-1-yl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  2-Azolylchromone Derivatives as Potent and Selective Inhibitors of Monoamine Oxidases A and B

  摘要：

  合成了一系列2-氮杂环色酮衍生物，并评估了它们对单胺氧化酶（MAO）A和B的抑制活性。在合成的化合物中，化合物1b、2b、4a-c、5b和7b对MAO-A显示出强效抑制活性（IC50值：1b: 0.32 µM；2b: 0.14 µM；4a: 0.11 µM；4b: 0.023 µM；4c: 0.15 µM；5b: 0.59 µM；7b: 0.19 µM），而4a、4c、5a、5c、6c和8c对MAO-B则显示出抑制活性（IC50值：4a: 0.028 µM；4c: 0.019 µM；5a: 0.73 µM；5c: 0.28 µM；6c: 0.28 µM；8c: 0.27 µM）。这些数据表明，6-甲氧基取代基有利于MAO-A的抑制，而7-甲氧基取代基则有利于MAO-B的抑制。此外，化合物4b是MAO-A的最强抑制剂，而化合物4c是MAO-B的最强抑制剂。这是首次报道2-氮杂环色酮衍生物作为强效单胺氧化酶抑制剂的研究结果。这些结果表明，2-三氮唑基色酮结构可能是设计和开发新型单胺氧化酶抑制剂的有用框架，正如4a-c和5a-c的活性所证明的那样。

  DOI：

  10.1248/cpb.c16-00527

文献信息

• Oxidative regioselective amination of chromones exposes potent inhibitors of the hedgehog signaling pathway
  作者：Rajarshi Samanta、Rishikesh Narayan、Jonathan O. Bauer、Carsten Strohmann、Sonja Sievers、Andrey P. Antonchick

  DOI：10.1039/c4cc08376h

  日期：——

  A novel selective coupling of chromones with azoles for the synthesis of biologically active compounds was developed.

  一种新型的选择性偶联方法，用于合成具有生物活性的化合物，将环酮与唑类化合物结合。
• Chromone compounds, pharmaceutical compositions containing the same, and
  申请人：Kureha Chemical Industry Co., Ltd.

  公开号：US05698575A1

  公开（公告）日：1997-12-16

  A chromone derivative of the formula (I): ##STR1## wherein R.sup.11 is a pyrazolyl, pyrrolyl, triazolyl, benzotriazolyl, benzimidazolyl, indazolyl, or indolyl group, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 is independently a hydrogen or halogen atom, or a hydroxy or alkoxy group, or an alkoxy group substituted with one or more alkoxy groups, and X is an oxygen or sulfur atom, or a salt thereof is disclosed. The chromone derivative inhibits the activity of matrix metalloproteinase.

  公开了一种具有以下结构的咖啡酮衍生物（I）：其中R.sup.11是吡唑基、吡咯基、三唑基、苯并三唑基、苯并咪唑基、吲哚基或吲哚基，R.sup.2、R.sup.3、R.sup.4和R.sup.5分别是氢或卤素原子，或羟基或烷氧基，或一个或多个烷氧基取代的烷氧基，X是氧或硫原子，或其盐。这种咖啡酮衍生物可以抑制基质金属蛋白酶的活性。
• Reaction of 3-Iodochromone with Nucleophile 1. Reaction of 3-Iodochromone with Azoles
  作者：Ichiro Yokoe、Yoshiaki Sugita

  DOI：10.3987/com-96-7615

  日期：——
• 2-Azolylchromone Derivatives as Potent and Selective Inhibitors of Monoamine Oxidases A and B
  作者：Koichi Takao、Takayuki Saito、Daisuke Chikuda、Yoshiaki Sugita

  DOI：10.1248/cpb.c16-00527

  日期：——

  A series of 2-azolylchromone derivatives were synthesized and their monoamine oxidase (MAO) A and B inhibitory activities were evaluated. Of the synthesized compounds, compounds 1b, 2b, 4a–c, 5b and 7b showed potent inhibitory activities against MAO-A (IC50 values, 1b: 0.32 µM; 2b: 0.14 µM; 4a: 0.11 µM; 4b: 0.023 µM; 4c: 0.15 µM; 5b: 0.59 µM; 7b: 0.19 µM) and 4a, c, 5a, c, 6c and 8c for MAO-B (IC50 values, 4a: 0.028 µM; 4c: 0.019 µM; 5a: 0.73 µM; 5c: 0.28 µM; 6c: 0.28 µM; 8c: 0.27 µM). These data suggest that 6-methoxy substitution favors MAO-A inhibition and 7-methoxy substitution favors MAO-B inhibition. In addition, compound 4b was the most potent inhibitor for MAO-A, and compound 4c for MAO-B. This is the first report identifying 2-azolylchromone derivatives as potent monoamine oxidase inhibitors. These results suggest that the 2-triazolylchromone structure may be a useful scaffold for the design and development of novel monoamine oxidase inhibitors, as evidenced by the activities of 4a–c and 5a–c.

  合成了一系列2-氮杂环色酮衍生物，并评估了它们对单胺氧化酶（MAO）A和B的抑制活性。在合成的化合物中，化合物1b、2b、4a-c、5b和7b对MAO-A显示出强效抑制活性（IC50值：1b: 0.32 µM；2b: 0.14 µM；4a: 0.11 µM；4b: 0.023 µM；4c: 0.15 µM；5b: 0.59 µM；7b: 0.19 µM），而4a、4c、5a、5c、6c和8c对MAO-B则显示出抑制活性（IC50值：4a: 0.028 µM；4c: 0.019 µM；5a: 0.73 µM；5c: 0.28 µM；6c: 0.28 µM；8c: 0.27 µM）。这些数据表明，6-甲氧基取代基有利于MAO-A的抑制，而7-甲氧基取代基则有利于MAO-B的抑制。此外，化合物4b是MAO-A的最强抑制剂，而化合物4c是MAO-B的最强抑制剂。这是首次报道2-氮杂环色酮衍生物作为强效单胺氧化酶抑制剂的研究结果。这些结果表明，2-三氮唑基色酮结构可能是设计和开发新型单胺氧化酶抑制剂的有用框架，正如4a-c和5a-c的活性所证明的那样。
• Syntheses and Evaluation of 2- or 3-(<i>N</i>-Cyclicamino)chromone Derivatives as Monoamine Oxidase Inhibitors
  作者：Koichi Takao、Tsukasa Sakatsume、Hitoshi Kamauchi、Yoshiaki Sugita

  DOI：10.1248/cpb.c20-00579

  日期：2020.11.1

  A series of 2-(N-cyclicamino)chromone derivatives (1a-4c) and 3-(N-cyclicamino)chromone derivatives (5a-8c) were synthesized, and their monoamine oxidase (MAO) A and B inhibitory activities were studied as part of a structure-activity relationship investigation. Compounds 1a-4c showed no remarkable inhibition for MAO-A or MAO-B, whereas compounds 5a-8c (with a few exceptions) showed significant and selective inhibition of MAO-B. Of these compounds, 7c,7-methoxy-3-(4-phenyl-1-piperazinyl)-4H-1-benzopyran-4-one inhibited MAO-B the most potently and selectively, having IC50 of 15 nM and an MAO-B selectivity index of more than 6700; c.f, 50 nM and 2000, respectively, for safinamide. The mode of inhibition of 7c to MAO-B was competitive and reversible. Considering the IC50 values and selectivity indices of the other synthetic compounds, the presence of the methoxy group on the chromone ring (R-2) of 7c seemed to increase MAO-B inhibition. Molecular docking analysis also supports this hypothesis. Our results suggest that 3-(N-cyclicamino)chromones are useful lead compounds for the development of MAO-B inhibitors.