2-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-2-ylthio)acetic acid | 58097-84-0

• 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: 2-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-2-ylthio)acetic acid
• 英文别名: (6-amino-9-β-D-ribofuranosyl-9H-purin-2-ylsulfanyl)-acetic acid；2-carboxymethylthioadenosine；2-Carboxymethylthio-adenosine；2-Carboxymethylthioadenosin；2-[6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]sulfanylacetic acid
• CAS: 58097-84-0
• 化学式: C₁₂H₁₅N₅O₆S
• 分子量: 357.347
• InChiKey: PBCOOMVAWMAWKA-TZQXKBMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  202
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-硫代腺苷酸 、 溴乙酸 以 sodium hydroxide 为溶剂， 以88%的产率得到2-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-2-ylthio)acetic acid
  参考文献：
  名称：

  S-substituted-2-thioadenosines

  摘要：

  S-取代的2-硫腺苷，由公式(I)表示：##SPC1## 其中R如下文定义，可用作血小板聚集抑制剂和冠脉血管舒张剂。

  公开号：

  US03968102A1

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.
• US3968102A
  申请人：——

  公开号：US3968102A

  公开（公告）日：1976-07-06
• S-substituted-2-thioadenosines
  申请人：Kohjin Co., Ltd.

  公开号：US03968102A1

  公开（公告）日：1976-07-06

  S-Substituted-2-thioadenosines represented by the formula (I): ##SPC1## wherein R is as defined hereinafter, useful as a platelet aggregation inhibitor and a coronary vasodilator.

  S-取代的2-硫腺苷，由公式(I)表示：##SPC1## 其中R如下文定义，可用作血小板聚集抑制剂和冠脉血管舒张剂。