N-(4-amino-1,3-dimethyl-2,6-dioxopyrimidin-5-yl)-4-methoxybenzamide | 166115-69-1

• 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-amino-1,3-dimethyl-2,6-dioxopyrimidin-5-yl)-4-methoxybenzamide
• CAS: 166115-69-1
• 化学式: C₁₄H₁₆N₄O₄
• 分子量: 304.305
• InChiKey: KFMGAQDEJWJLCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-amino-1,3-dimethyl-2,6-dioxopyrimidin-5-yl)-4-methoxybenzamide 在 三氯化铝 、 phosphorus pentoxide 作用下， 以 吡啶 为溶剂， 反应 4.0h， 以30%的产率得到1,3-dimethyl-8-(4-methoxyphenyl)-9(H)-xanthine
  参考文献：
  名称：

  Synthesis and in vitro bronchospasmolytic activity of 8-aryl, heteroaryl or arylalkyl theophyllines

  摘要：

  Twenty-four 8-aryl- or 8-heteroaryl-substituted theophyllines have been synthesized. The substituents are aromatic rings and heterocycles likely to induce an antiallergic effect or a spasmolytic activity. In vitro evaluation of the bronchospasm caused by acetylcholine or histamine shows an interesting activity for half of the compounds. Among them, the furanic IIIs and 2-chlorophenyl IIIi derivatives are, for instance, four times more active than theophylline.

  DOI：

  10.1016/0223-5234(96)88233-x
• 作为产物：
  描述：

  5,6-二氨基-1,3-二甲基脲嘧啶 、 对甲氧基苯甲酰氯 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以10%的产率得到N-(4-amino-1,3-dimethyl-2,6-dioxopyrimidin-5-yl)-4-methoxybenzamide
  参考文献：
  名称：

  Synthesis and in vitro bronchospasmolytic activity of 8-aryl, heteroaryl or arylalkyl theophyllines

  摘要：

  Twenty-four 8-aryl- or 8-heteroaryl-substituted theophyllines have been synthesized. The substituents are aromatic rings and heterocycles likely to induce an antiallergic effect or a spasmolytic activity. In vitro evaluation of the bronchospasm caused by acetylcholine or histamine shows an interesting activity for half of the compounds. Among them, the furanic IIIs and 2-chlorophenyl IIIi derivatives are, for instance, four times more active than theophylline.

  DOI：

  10.1016/0223-5234(96)88233-x

文献信息

• Exploration of polystyrene-supported 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline (PS-IIDQ) as new coupling agent for the synthesis of 8-substituted xanthine derivatives
  作者：Prabal Bandyopadhyay、Manisha Sathe、Pratibha Sharma、M.P. Kaushik

  DOI：10.1016/j.tetlet.2012.04.135

  日期：2012.8

  Polystyrene-supported 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline (PS-IIDQ), a polymer supported covalent coupling reagent, was successfully employed for the first time in the synthesis of 8-substituted xanthine derivatives. PS-IIDQ was observed to be more efficient than IIDQ and polymer-supported carbodiimide (PS-EDC). (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and in vitro bronchospasmolytic activity of 8-aryl, heteroaryl or arylalkyl theophyllines
  作者：G Baziard-Mouysset、A Rached、S Younes、C Tournaire、JL Stigliani、M Payard、JC Yavo、C Advenier

  DOI：10.1016/0223-5234(96)88233-x

  日期：1995.1

  Twenty-four 8-aryl- or 8-heteroaryl-substituted theophyllines have been synthesized. The substituents are aromatic rings and heterocycles likely to induce an antiallergic effect or a spasmolytic activity. In vitro evaluation of the bronchospasm caused by acetylcholine or histamine shows an interesting activity for half of the compounds. Among them, the furanic IIIs and 2-chlorophenyl IIIi derivatives are, for instance, four times more active than theophylline.