N-(2-amino-1-ethyl)-4-hydroxy-2-oxo-2H-chromene-3-carboxamide | 27280-78-0

• 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: N-(2-amino-1-ethyl)-4-hydroxy-2-oxo-2H-chromene-3-carboxamide
• 英文别名: N-(2-aminoethyl)-4-hydroxy-2-oxo-2H-chromene-3-carboxamide；N-(2-aminoethyl)-4-hydroxy-2-oxochromene-3-carboxamide
• CAS: 27280-78-0
• 化学式: C₁₂H₁₂N₂O₄
• 分子量: 248.238
• InChiKey: OXGJLKFODUSQGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-amino-1-ethyl)-4-hydroxy-2-oxo-2H-chromene-3-carboxamide 、 DL-α-硫辛酸-NHS 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到N-(2-(4-(1,2-dithiolan-3-yl)pentanamido)ethyl)-4-hydroxy-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their alpha-lipoic acid adducts

  摘要：

  In the present work a series of novel coumarin-3-carboxamides and their hybrids with the alpha-lipoic acid were designed, synthesized and tested as potent antioxidant and anti-inflammatory agents. The new compounds were evaluated for their antioxidant activity, their activity to inhibit in vitro lipoxygenase and their in vivo anti-inflammatory activity. In general, the derivatives were generally found to present antioxidant and anti-inflammatory activities. Discussion is made based on the results for the structure-activity relationships in order to define the structural features required for activity. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.12.027
• 作为产物：
  描述：

  4-hydroxy-3-methoxycarbonylcoumarin 、 乙二胺 以 甲苯 为溶剂， 生成 N-(2-amino-1-ethyl)-4-hydroxy-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  香豆素和喹啉酮羧酰胺类抗癌药的合成，X射线晶体学研究及其生物学评价

  摘要：

  摘要合成了一系列香豆素和喹啉酮-3-氨基酰胺衍生物，并评估了其抑制癌细胞生长的潜能。的结构ñ - [2-（二甲基氨基）乙基] -4-羟基-2-氧代-1-苯基-1,2-二氢喹啉-3-甲酰胺是明确地通过X射线衍射分析，其显示所确认的顺式构象由两个分子内氢键的存在而产生的酰胺键 图形概要

  DOI：

  10.1007/s00706-013-0986-7

文献信息

• Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their alpha-lipoic acid adducts
  作者：Georgia Melagraki、Antreas Afantitis、Olga Igglessi-Markopoulou、Anastasia Detsi、Maria Koufaki、Christos Kontogiorgis、Dimitra J. Hadjipavlou-Litina

  DOI：10.1016/j.ejmech.2008.12.027

  日期：2009.7

  In the present work a series of novel coumarin-3-carboxamides and their hybrids with the alpha-lipoic acid were designed, synthesized and tested as potent antioxidant and anti-inflammatory agents. The new compounds were evaluated for their antioxidant activity, their activity to inhibit in vitro lipoxygenase and their in vivo anti-inflammatory activity. In general, the derivatives were generally found to present antioxidant and anti-inflammatory activities. Discussion is made based on the results for the structure-activity relationships in order to define the structural features required for activity. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Synthesis, X-ray crystallographic study, and biological evaluation of coumarin and quinolinone carboxamides as anticancer agents
  作者：Dimitris Matiadis、Valentina Stefanou、Giorgos Athanasellis、Stylianos Hamilakis、Vickie McKee、Olga Igglessi-Markopoulou、John Markopoulos

  DOI：10.1007/s00706-013-0986-7

  日期：2013.7

  evaluated for its potency in inhibition of cancer cell growth. The structure of N-[2-(dimethylamino) ethyl]-4-hydroxy-2-oxo-1-phenyl-1,2-dihydroquinoline-3-carboxamide was unambiguously confirmed by X-ray diffraction analysis, which revealed the cis conformation of the amide bond resulting from the presence of two intramolecular hydrogen bonds. Graphical Abstract

  摘要合成了一系列香豆素和喹啉酮-3-氨基酰胺衍生物，并评估了其抑制癌细胞生长的潜能。的结构ñ - [2-（二甲基氨基）乙基] -4-羟基-2-氧代-1-苯基-1,2-二氢喹啉-3-甲酰胺是明确地通过X射线衍射分析，其显示所确认的顺式构象由两个分子内氢键的存在而产生的酰胺键 图形概要