4-(2-hydroxymethyl-3-nitrobenzoyl)imidazole-1-sulfonic acid dimethylamide | 355133-61-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-hydroxymethyl-3-nitrobenzoyl)imidazole-1-sulfonic acid dimethylamide
• 英文别名: 4-[2-(hydroxymethyl)-3-nitrobenzoyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide；4-[2-(hydroxymethyl)-3-nitrobenzoyl]-N,N-dimethylimidazole-1-sulfonamide
• CAS: 355133-61-8
• 化学式: C₁₃H₁₄N₄O₆S
• 分子量: 354.343
• InChiKey: RPCOUZGZXXFFPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(2-hydroxymethyl-3-nitrobenzoyl)imidazole-1-sulfonic acid dimethylamide 在 palladium on activated charcoal 吡啶 、 盐酸 、 三乙基硅烷 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 19.0h， 生成 N-[1-(1H-imidazol-4-yl)-1,3-dihydro-2-benzofuran-4-yl]ethanesulfonamide
  参考文献：
  名称：

  Synthesis and Structure−Activity Studies on N-[5-(1H-Imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide, an Imidazole-Containing α_1A-Adrenoceptor Agonist

  摘要：

  Structure-activity studies were performed on the alpha(1A)-adrenoceptor (AR) selective agonist N-[5-(1H-imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide (4). Compounds were evaluated for binding activity at the alpha(1A), alpha(1b), alpha(1d), alpha(2a), and alpha(2B) subtypes. Functional activity in tissues containing the alpha(1A) (rabbit urethra), alpha(1B) (rat spleen), alpha(1D) (rat aorta), and alpha(2A) (rat prostatic vas deferens) was also evaluated. A dog in vivo model simultaneously measuring intraurethral pressure (IUP) and mean arterial pressure (ALAP) was used to assess the uroselectivity of the compounds. Many of the compounds that were highly selective in vitro for the alpha(1A)-AR subtype were also more uroselective in vivo for increasing IUP over MAP than the nonselective alpha(1)-agonists phenylpropanolamine (PPA) (1) and ST-1059 (2, the active metabolite of midodrine), supporting the hypothesis that greater alpha(1A) selectivity would reduce cardiovascular side effects. However, the data also support a prominent role of the alpha(1A)-AR subtype in the control of MAP.

  DOI：

  10.1021/jm030551a
• 作为产物：
  描述：

  4-硝基苯酞 、 N,N-二甲基-4-碘-1H-咪唑-1-磺酰胺 生成 4-(2-hydroxymethyl-3-nitrobenzoyl)imidazole-1-sulfonic acid dimethylamide
  参考文献：
  名称：

  4-Imidazole derivatives of benzyl and restricted benzyl sulfonamides, sulfamides, ureas, carbamates, and amides and their use

  摘要：

  公式I1的化合物在治疗由或减轻α1A激动剂预防的疾病方面非常有用。此外，还披露了α1A激动剂组合物和在哺乳动物体内激活α1肾上腺素能受体的方法。

  公开号：

  US20030073850A1