4-(3-aminophenylsulfanyl)imidazole-1-sulfonic acid dimethylamide | 725233-27-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(3-aminophenylsulfanyl)imidazole-1-sulfonic acid dimethylamide
• 英文别名: 4-(3-aminophenyl)sulfanyl-N,N-dimethylimidazole-1-sulfonamide
• CAS: 725233-27-2
• 化学式: C₁₁H₁₄N₄O₂S₂
• 分子量: 298.39
• InChiKey: DWZXNQNEFXMLFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(3-aminophenylsulfanyl)imidazole-1-sulfonic acid dimethylamide 在 吡啶 、 盐酸 、 过氧乙酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 N-[3-(1H-imidazol-5-ylsulfonyl)phenyl]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：

  3,3'-二硝基二苯二硫醚 在 乙基溴化镁 、 铁粉 、 氯化铵 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 17.0h， 生成 4-(3-aminophenylsulfanyl)imidazole-1-sulfonic acid dimethylamide
  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

• Synthesis and Structure−Activity Studies on <i>N</i>-[5-(1<i>H</i>-Imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide, an Imidazole-Containing α_1A-Adrenoceptor Agonist
  作者：Robert J. Altenbach、Albert Khilevich、Teodozyj Kolasa、Jeffrey J. Rohde、Pramila A. Bhatia、Meena V. Patel、Xenia B. Searle、Fan Yang、William H. Bunnelle、Karin Tietje、Erol K. Bayburt、William A. Carroll、Michael D. Meyer、Rodger Henry、Steven A. Buckner、Jane Kuk、Anthony V. Daza、Ivan V. Milicic、John C. Cain、Chae H. Kang、Lynne M. Ireland、Tracy L. Carr、Thomas R. Miller、Arthur A. Hancock、Masaki Nakane、Timothy A. Esbenshade、Michael E. Brune、Alyssa B. O'Neill、Donna M. Gauvin、Sweta P. Katwala、Mark W. Holladay、Jorge D. Brioni、James P. Sullivan

  DOI：10.1021/jm030551a

  日期：2004.6.1

  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.