N-((5-methoxypyridin-2-yl)methyl)-4-(1-methyl-2,4-dioxo-3-propyl-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)benzenesulfonamide | 905306-63-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-((5-methoxypyridin-2-yl)methyl)-4-(1-methyl-2,4-dioxo-3-propyl-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)benzenesulfonamide
• 英文别名: N-[(5-methoxypyridin-2-yl)methyl]-4-(1-methyl-2,4-dioxo-3-propyl-5H-pyrrolo[3,2-d]pyrimidin-6-yl)benzenesulfonamide
• CAS: 905306-63-0
• 化学式: C₂₃H₂₅N₅O₅S
• 分子量: 483.548
• InChiKey: QQQVIQPNCAWTAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-(1-methyl-2,4-dioxo-3-propyl-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl) benzenesulphonyl chloride 、 5-甲氧基-2-吡啶甲胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-((5-methoxypyridin-2-yl)methyl)-4-(1-methyl-2,4-dioxo-3-propyl-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)benzenesulfonamide
  参考文献：
  名称：

  New pyrrolopyrimidin-6-yl benzenesulfonamides: Potent A2B adenosine receptor antagonists

  摘要：

  A new series of 4-(1,3-dialkyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)benzenesulfonamides has been identified as potent AZB adenosine receptor antagonists. The products have been evaluated for their binding affinities for the human A(2B), A(1) and A(3) adenosine receptors. 6-(4-{[4-(4-Bromobenzyl)piperazin-1-yl]sulfonyl}phenyl)-1,3-dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (16) showed a high affinity for the AZB adenosine receptor (IC50 = 1 nM) and selectivity (A(1): 183x; A(30): 12660x). Synthesis and SAR of this novel class of compounds showing improved absorption properties is presented herein. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.074

文献信息

• New pyrrolopyrimidin-6-yl benzenesulfonamides: Potent A2B adenosine receptor antagonists
  作者：Cristina Esteve、Arsenio Nueda、José Luis Díaz、Jorge Beleta、Alvaro Cárdenas、Estrella Lozoya、Maria Isabel Cadavid、Maria Isabel Loza、Hamish Ryder、Bernat Vidal

  DOI：10.1016/j.bmcl.2006.04.074

  日期：2006.7

  A new series of 4-(1,3-dialkyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)benzenesulfonamides has been identified as potent AZB adenosine receptor antagonists. The products have been evaluated for their binding affinities for the human A(2B), A(1) and A(3) adenosine receptors. 6-(4-[4-(4-Bromobenzyl)piperazin-1-yl]sulfonyl}phenyl)-1,3-dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (16) showed a high affinity for the AZB adenosine receptor (IC50 = 1 nM) and selectivity (A(1): 183x; A(30): 12660x). Synthesis and SAR of this novel class of compounds showing improved absorption properties is presented herein. (c) 2006 Elsevier Ltd. All rights reserved.