Ethanesulfonic acid [5-hydroxy-5-(1-trityl-1H-imidazol-4-yl)-5,6,7,8-tetrahydro-naphthalen-1-yl]-amide | 725233-11-4

• 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: Ethanesulfonic acid [5-hydroxy-5-(1-trityl-1H-imidazol-4-yl)-5,6,7,8-tetrahydro-naphthalen-1-yl]-amide
• CAS: 725233-11-4
• 化学式: C₃₄H₃₃N₃O₃S
• 分子量: 563.72
• InChiKey: GZWZSRIBBRZAEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.06
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  84.22
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Ethanesulfonic acid [5-hydroxy-5-(1-trityl-1H-imidazol-4-yl)-5,6,7,8-tetrahydro-naphthalen-1-yl]-amide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 53.0h， 以26%的产率得到Ethanesulfonic acid [5-hydroxy-5-(1H-imidazol-4-yl)-5,6,7,8-tetrahydro-naphthalen-1-yl]-amide
  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-[1-(1-hydroxy-5-nitro-1,2,3,4-tetrahydronaphthyl)]-1-tritylimidazole 在 吡啶 、 铁粉 、 氯化铵 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 Ethanesulfonic acid [5-hydroxy-5-(1-trityl-1H-imidazol-4-yl)-5,6,7,8-tetrahydro-naphthalen-1-yl]-amide
  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