4-[hydroxy(3-nitrophenyl)methyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide | 258528-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[hydroxy(3-nitrophenyl)methyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide
• 英文别名: 4-[hydroxy-(3-nitrophenyl)methyl]-N,N-dimethylimidazole-1-sulfonamide
• CAS: 258528-27-7
• 化学式: C₁₂H₁₄N₄O₅S
• 分子量: 326.333
• InChiKey: AUWVXQRBICOANJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[hydroxy(3-nitrophenyl)methyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide 在 barium manganate 作用下， 以 甲苯 为溶剂， 以9.7 g (84%)的产率得到N,N-dimethyl-4-(3-nitrobenzoyl)-1H-imidazole-1-sulfonamide
  参考文献：
  名称：

  Imidazoles and related compounds as &agr;1A agonists

  摘要：

  具有化学式I的化合物在治疗由α1A激动剂预防或缓解的疾病中很有用。还公开了α1A激动剂组合物和在哺乳动物中激活α1肾上腺素受体的方法。

  公开号：

  US06503935B1
• 作为产物：
  描述：

  间硝基苯甲醛 、 N,N-二甲基-4-碘-1H-咪唑-1-磺酰胺 在 乙基溴化镁 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 4-[hydroxy(3-nitrophenyl)methyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide
  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

文献信息

• 4-Imidazole derivatives of benzyl and restricted benzyl sulfonamides, sulfamides, ureas, carbamates, and amides and their use
  申请人：——

  公开号：US20030073850A1

  公开（公告）日：2003-04-17

  Compounds of formula I 1 are useful in treating diseases prevented by or ameliorated with &agr; 1A agonists. Also disclosed are &agr; 1A agonist compositions and a method of activating &agr; 1 adrenoceptors in a mammal.

  公式I的化合物在治疗由&agr; 1A激动剂预防或改善的疾病中很有用。还公开了&agr; 1A激动剂组合物和在哺乳动物中激活&agr; 1肾上腺素受体的方法。
• <i>N</i>-[3-(1<i>H</i>-Imidazol-4-ylmethyl)phenyl]ethanesulfonamide (ABT-866, 1), a Novel α₁-Adrenoceptor Ligand with an Enhanced in Vitro and in Vivo Profile Relative to Phenylpropanolamine and Midodrine
  作者：Robert J. Altenbach、Albert Khilevich、Michael D. Meyer、Steven A. Buckner、Ivan Milicic、Anthony V. Daza、Michael E. Brune、Alyssa B. O'Neill、Donna M. Gauvin、John C. Cain、Masaki Nakane、Mark W. Holladay、Michael Williams、Jorge D. Brioni、James P. Sullivan

  DOI：10.1021/jm025550h

  日期：2002.9.1

  N-[3-(1H-Imidazol-4-ylmethyl)phenyl]ethanesulfonamide (ABT-866, 1) is a novel alpha(1) agent having the unique profile of alpha(1A) (rabbit urethra, EC50 = 0.60 muM) agonism with alpha(1B) (rat spleen, pA(2) = 5.4) and alpha(1D) (rat aorta, pA(2) = 6.2) antagonism. An in vivo dog model showed I to be more selective for the urethra over the vasculature than A-61603 (2), ST-1059 (3, the active metabolite of midodrine), and phenylpropanolamine (4).
• US6503935B1
  申请人：——

  公开号：US6503935B1

  公开（公告）日：2003-01-07