Cyclopentanecarboxylic acid (6-amino-1,3-dimethyl-4-oxo-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide | 121543-16-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Cyclopentanecarboxylic acid (6-amino-1,3-dimethyl-4-oxo-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide
• CAS: 121543-16-6
• 化学式: C₁₂H₁₈N₄O₂S
• 分子量: 282.367
• InChiKey: AOKKFQGXBNLTRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  82.05
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Cyclopentanecarboxylic acid (6-amino-1,3-dimethyl-4-oxo-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide 在 sodium hydroxide 、 tetraphosphorus decasulfide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 6.0h， 生成 8-Cyclopentyl-1,3-dimethyl-3,7-dihydro-purine-2,6-dithione
  参考文献：
  名称：

  Sulfur-containing 1,3-dialkylxanthine derivatives as selective antagonists at A1-adenosine receptors

  摘要：

  Sulfur-containing analogues of 8-substituted xanthines were prepared in an effort to increase selectivity or potency as antagonists at adenosine receptors. Either cyclopentyl or various aryl substituents were utilized at the 8-position, because of the association of these groups with high potency at A1-adenosine receptors. Sulfur was incorporated on the purine ring at positions 2 and/or 6, in the 8-position substituent in the form of 2- or 3-thienyl groups, or via thienyl groups separated from an 8-aryl substituent through an amide-containing chain. The feasibility of using the thienyl group as a prosthetic group for selective iodination via its Hg2+ derivative was explored. Receptor selectivity was determined in binding assays using membrane homogenates from rat cortex [( 3H]-N6-(phenylisopropyl)adenosine as radioligand] or striatum [3H]-5'-(N-ethylcarbamoyl)adenosine as radioligand] for A1- and A2-adenosine receptors, respectively. Generally, 2-thio-8-cycloalkylxanthines were at least as A1 selective as the corresponding oxygen analogue. 2-Thio-8-aryl derivatives tended to be more potent at A2 receptors than the oxygen analogue. 8-[4-[(Carboxy-methyl)oxyl] phenyl]-1,3-dipropyl-2-thioxanthine ethyl ester was greater than 740-fold A1 selective.

  DOI：

  10.1021/jm00128a031
• 作为产物：
  描述：

  环戊基甲酰氯 、 1,3-dimethyl-5,6-diamino-2-thiouracil 在 吡啶 作用下， 反应 5.0h， 以71%的产率得到Cyclopentanecarboxylic acid (6-amino-1,3-dimethyl-4-oxo-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide
  参考文献：
  名称：

  Sulfur-containing 1,3-dialkylxanthine derivatives as selective antagonists at A1-adenosine receptors

  摘要：

  Sulfur-containing analogues of 8-substituted xanthines were prepared in an effort to increase selectivity or potency as antagonists at adenosine receptors. Either cyclopentyl or various aryl substituents were utilized at the 8-position, because of the association of these groups with high potency at A1-adenosine receptors. Sulfur was incorporated on the purine ring at positions 2 and/or 6, in the 8-position substituent in the form of 2- or 3-thienyl groups, or via thienyl groups separated from an 8-aryl substituent through an amide-containing chain. The feasibility of using the thienyl group as a prosthetic group for selective iodination via its Hg2+ derivative was explored. Receptor selectivity was determined in binding assays using membrane homogenates from rat cortex [( 3H]-N6-(phenylisopropyl)adenosine as radioligand] or striatum [3H]-5'-(N-ethylcarbamoyl)adenosine as radioligand] for A1- and A2-adenosine receptors, respectively. Generally, 2-thio-8-cycloalkylxanthines were at least as A1 selective as the corresponding oxygen analogue. 2-Thio-8-aryl derivatives tended to be more potent at A2 receptors than the oxygen analogue. 8-[4-[(Carboxy-methyl)oxyl] phenyl]-1,3-dipropyl-2-thioxanthine ethyl ester was greater than 740-fold A1 selective.

  DOI：

  10.1021/jm00128a031