PSB-0777 | 1341190-47-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: PSB-0777
• 英文别名: 4-(2-(6-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-2-ylthio)ethyl)benzene sulfonic acid；4-[2-[6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]sulfanylethyl]benzenesulfonic acid
• CAS: 1341190-47-3
• 化学式: C₁₈H₂₁N₅O₇S₂
• 分子量: 483.526
• InChiKey: MSSJGFVZLYCDOA-LSCFUAHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  228
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  PSB-0777 在 间氯过氧苯甲酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 4-(2-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-2-ylsulfonyl)ethyl)benzenesulfonic acid
  参考文献：
  名称：

  Development of Polar Adenosine A_2A Receptor Agonists for Inflammatory Bowel Disease: Synergism with A_2B Antagonists

  摘要：

  Adenosine A(2A) receptor agonists for the local treatment of inflammatory bowel disease (IBS) were designed and synthesized. Polar groups were introduced to prevent peroral absorption and subsequent systemic, e.g., hypotensive, side effects. 4-(2-{6-Amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-9H-purin-2-ylthio}ethyl)-benzenesulfonic acid (7, PSB-0777) was selected for further evaluation in rat ileum/jejunum preparations in ex vivo experiments. Compound 7 significantly improved impaired acetylcholine-induced contractions induced by 2,4,6-trinitrobenzenesulfonic acid and showed synergism with an A(2B)-selective antagonist. Thus, nonabsorbable, locally active A(2A) agonists, as a monotherapy or in combination with an A(2B) antagonist, may be an efficient novel treatment for IBS, preventing the severe systemic side effects of known A(2A) agonists.

  DOI：

  10.1021/ml200189u
• 作为产物：
  描述：

  腺苷 在 双氧水 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 生成 PSB-0777
  参考文献：
  名称：

  Development of Polar Adenosine A_2A Receptor Agonists for Inflammatory Bowel Disease: Synergism with A_2B Antagonists

  摘要：

  Adenosine A(2A) receptor agonists for the local treatment of inflammatory bowel disease (IBS) were designed and synthesized. Polar groups were introduced to prevent peroral absorption and subsequent systemic, e.g., hypotensive, side effects. 4-(2-{6-Amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-9H-purin-2-ylthio}ethyl)-benzenesulfonic acid (7, PSB-0777) was selected for further evaluation in rat ileum/jejunum preparations in ex vivo experiments. Compound 7 significantly improved impaired acetylcholine-induced contractions induced by 2,4,6-trinitrobenzenesulfonic acid and showed synergism with an A(2B)-selective antagonist. Thus, nonabsorbable, locally active A(2A) agonists, as a monotherapy or in combination with an A(2B) antagonist, may be an efficient novel treatment for IBS, preventing the severe systemic side effects of known A(2A) agonists.

  DOI：

  10.1021/ml200189u

文献信息

• Development of Polar Adenosine A_2A Receptor Agonists for Inflammatory Bowel Disease: Synergism with A_2B Antagonists
  作者：Ali El-Tayeb、Sebastian Michael、Aliaa Abdelrahman、Andrea Behrenswerth、Sabrina Gollos、Karen Nieber、Christa E. Müller

  DOI：10.1021/ml200189u

  日期：2011.12.8

  Adenosine A(2A) receptor agonists for the local treatment of inflammatory bowel disease (IBS) were designed and synthesized. Polar groups were introduced to prevent peroral absorption and subsequent systemic, e.g., hypotensive, side effects. 4-(2-6-Amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-9H-purin-2-ylthio}ethyl)-benzenesulfonic acid (7, PSB-0777) was selected for further evaluation in rat ileum/jejunum preparations in ex vivo experiments. Compound 7 significantly improved impaired acetylcholine-induced contractions induced by 2,4,6-trinitrobenzenesulfonic acid and showed synergism with an A(2B)-selective antagonist. Thus, nonabsorbable, locally active A(2A) agonists, as a monotherapy or in combination with an A(2B) antagonist, may be an efficient novel treatment for IBS, preventing the severe systemic side effects of known A(2A) agonists.