5-amino-6-methyl-chromen-2-one

• 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: 5-amino-6-methyl-chromen-2-one
• 英文别名: 5-Amino-6-methylchromen-2-one
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: QVCIYAWCVGXSDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-6-methyl-chromen-2-one 在 Grubbs catalyst first generation 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 365.0h， 生成 6-methyl-5-(1H-pyrrol-1-yl)-2H-chromen-2-one 、 5-(2,5-dihydro-1H-pyrrol-1-yl)-6-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of (2,5-dihydro-1H-pyrrol-1-yl)-2H-chromen-2-ones as free radical scavengers

  摘要：

  The allylation of aminocoumarins in the presence of excess of anhydrous K2CO3 and allyl bromide to diallylaminocoumarins is described. The Ring Closing Metathesis reaction of the later with the Grubbs' 1rst generation catalyst under reflux or MW irradiation has resulted mainly to (2,5-dihydro-1H-pyrrol-1-yl)coumarins and (1H-pyrrol-1-yl)coumarins. The new compounds were tested in vitro for their ability: (i) to interact with 1,1-diphenyl-2-picryl-hydrazyl (DPPH) stable free radical, (ii) to inhibit lipid peroxidation, (iii) to scavenge the superoxide anion, (iv) to inhibit the activity of soybean lipoxygenase LO and (v) to scavenge hydroxyl radicals. Most of them were found to be potent lipid peroxidation inhibitors in vitro. The majority of the compounds showed significant hydroxyl radical scavenging activity. Compounds 11a and 12c presenting higher LO inhibitory activity as well as compound 17 were found to present a promising antioxidant and LO inhibitory profile. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.053
• 作为产物：
  描述：

  6-甲基香豆素 在 palladium on activated charcoal sodium nitrate 、 甲酸 、 硫酸 、 三乙胺 、 sodium nitrite 作用下， 反应 3.33h， 生成 5-amino-6-methyl-chromen-2-one
  参考文献：
  名称：

  Lin, Shaw-Tao; Yang, Fu-May; Yang, Heuy-Ju, Journal of Chemical Research - Part S, 1995, # 9, p. 372 - 373

  摘要：

  DOI：

文献信息

• Development of Fluorogenic Substrates For Monoamine Oxidases (Mao-A and Mao-B)
  申请人：Chen Gong

  公开号：US20080194522A1

  公开（公告）日：2008-08-14

  The present invention relates to compounds useful for detecting the activity of monoamine oxidases, compounds useful for competitively inhibiting monoamine oxidases, for determining inhibitors of monoamine oxidases and compounds useful for treating monoamine oxidase-related nervous system pathologies, as well as pharmaceutical compositions and methods of manufacture thereof.

  本发明涉及用于检测单胺氧化酶活性的化合物，用于竞争性抑制单胺氧化酶的化合物，用于确定单胺氧化酶抑制剂和用于治疗与单胺氧化酶相关的神经系统病理的化合物，以及制药组合物和制造方法。
• Lin, Shaw-Tao; Yang, Fu-May; Yang, Heuy-Ju, Journal of Chemical Research - Part S, 1995, # 9, p. 372 - 373
  作者：Lin, Shaw-Tao、Yang, Fu-May、Yang, Heuy-Ju、Huang, Keh-Feng

  DOI：——

  日期：——
• Synthesis and biological evaluation of (2,5-dihydro-1H-pyrrol-1-yl)-2H-chromen-2-ones as free radical scavengers
  作者：Anna Balabani、Dimitra J. Hadjipavlou-Litina、Konstantinos E. Litinas、Maria Mainou、Crystal-Catherine Tsironi、Anastasia Vronteli

  DOI：10.1016/j.ejmech.2011.09.053

  日期：2011.12

  The allylation of aminocoumarins in the presence of excess of anhydrous K2CO3 and allyl bromide to diallylaminocoumarins is described. The Ring Closing Metathesis reaction of the later with the Grubbs' 1rst generation catalyst under reflux or MW irradiation has resulted mainly to (2,5-dihydro-1H-pyrrol-1-yl)coumarins and (1H-pyrrol-1-yl)coumarins. The new compounds were tested in vitro for their ability: (i) to interact with 1,1-diphenyl-2-picryl-hydrazyl (DPPH) stable free radical, (ii) to inhibit lipid peroxidation, (iii) to scavenge the superoxide anion, (iv) to inhibit the activity of soybean lipoxygenase LO and (v) to scavenge hydroxyl radicals. Most of them were found to be potent lipid peroxidation inhibitors in vitro. The majority of the compounds showed significant hydroxyl radical scavenging activity. Compounds 11a and 12c presenting higher LO inhibitory activity as well as compound 17 were found to present a promising antioxidant and LO inhibitory profile. (C) 2011 Elsevier Masson SAS. All rights reserved.