2-羟基乙基(1,3-二甲基-2,6-二氧代-1,2,3,6-四氢-7H-嘌呤-7-基)乙酸酯 | 61379-38-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-羟基乙基(1,3-二甲基-2,6-二氧代-1,2,3,6-四氢-7H-嘌呤-7-基)乙酸酯
• 英文名称: (1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-acetic acid 2-hydroxy-ethyl ester
• 英文别名: 2-Hydroxyethyl 1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purine-7-acetate；2-hydroxyethyl 2-(1,3-dimethyl-2,6-dioxopurin-7-yl)acetate
• CAS: 61379-38-2
• 化学式: C₁₁H₁₄N₄O₅
• 分子量: 282.256
• InChiKey: BSHFGYOWIYPMDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  茶碱乙酸 、 乙二醇 在 4-二甲氨基吡啶 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以63.5%的产率得到2-羟基乙基(1,3-二甲基-2,6-二氧代-1,2,3,6-四氢-7H-嘌呤-7-基)乙酸酯
  参考文献：
  名称：

  Synthesis, Toxicological, Pharmacological Assessment, and in Vitro Bronchodilating Activity of some 7-Theophyllinylacetyloxyglycols

  摘要：

  The synthesis of four ester derivatives of 7-theophylline-acetic acid and glycols by DCC/DMAP-mediated esterification under mild conditions was studied. The structures of the synthesized compounds were proved by microanalyses, UV-, IR-, and H-1-NMR data. Acute toxicity assessment of the compounds in mice showed that compounds 2a-d are less toxic than aminophylline. It was shown by in vivo experiments that 2a-d had depressive action on CNS (increasing of hexobarbital sleeping time and decreasing of spontaneous locomotor activity), and they did not influence to a statistically significant extent the normal 24 hour diuresis of rats (except 2c). The results of cardiovascular screening in rats show that compounds 2a and 2c decreased the heart rate of rats. A pharmacological study of the in vitro broncholytic effect (IC50 and pD(2) values) of the derivatives and aminophylline showed that 2c exhibited good broncholytic effect in vitro especially in acetylcholine and serotonin induced guinea pig tracheal contraction. It was demonstrated that compounds 2b,c exerted a stronger inhibitory effect on the enzymic activity of phosphodiesterase in concentration 2 x 10(-3) M than aminophylline.

  DOI：

  10.1002/(sici)1521-4184(199810)331:10<313::aid-ardp313>3.0.co;2-i

文献信息

• Synthesis, Toxicological, Pharmacological Assessment, and in Vitro Bronchodilating Activity of some 7-Theophyllinylacetyloxyglycols
  作者：Alexander Zlatkov、Plamen Peikov、Nikolai Danchev、Dimiter Ivanov、Boika Tsvetkova

  DOI：10.1002/(sici)1521-4184(199810)331:10<313::aid-ardp313>3.0.co;2-i

  日期：1998.10

  The synthesis of four ester derivatives of 7-theophylline-acetic acid and glycols by DCC/DMAP-mediated esterification under mild conditions was studied. The structures of the synthesized compounds were proved by microanalyses, UV-, IR-, and H-1-NMR data. Acute toxicity assessment of the compounds in mice showed that compounds 2a-d are less toxic than aminophylline. It was shown by in vivo experiments that 2a-d had depressive action on CNS (increasing of hexobarbital sleeping time and decreasing of spontaneous locomotor activity), and they did not influence to a statistically significant extent the normal 24 hour diuresis of rats (except 2c). The results of cardiovascular screening in rats show that compounds 2a and 2c decreased the heart rate of rats. A pharmacological study of the in vitro broncholytic effect (IC50 and pD(2) values) of the derivatives and aminophylline showed that 2c exhibited good broncholytic effect in vitro especially in acetylcholine and serotonin induced guinea pig tracheal contraction. It was demonstrated that compounds 2b,c exerted a stronger inhibitory effect on the enzymic activity of phosphodiesterase in concentration 2 x 10(-3) M than aminophylline.