3-(4-imidazol-1-ylphenylmethyl)-5-isobutyl-N-tert-butylthiophene-2-sulfonamide | 777865-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-imidazol-1-ylphenylmethyl)-5-isobutyl-N-tert-butylthiophene-2-sulfonamide
• 英文别名: N-(t-butyl)-3-[4-(1h-imidazol-1-yl)benzyl]-5-isobutylthiophene-2-sulfonamide；N-tert-butyl-3-[(4-imidazol-1-ylphenyl)methyl]-5-(2-methylpropyl)thiophene-2-sulfonamide
• CAS: 777865-65-3
• 化学式: C₂₂H₂₉N₃O₂S₂
• 分子量: 431.623
• InChiKey: YMVFFBLOUMFEIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-imidazol-1-ylphenylmethyl)-5-isobutyl-N-tert-butylthiophene-2-sulfonamide 在 吡啶 、 2-(吡咯烷-1-基)吡啶 、 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 butyl N-[3-[(4-imidazol-1-ylphenyl)methyl]-5-(2-methylpropyl)thiophen-2-yl]sulfonylcarbamate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of the First Selective Nonpeptide AT₂ Receptor Agonist

  摘要：

  The first druglike selective angiotensin II AT(2) receptor agonist (21) with a K-i value of 0.4 nM for the AT(2) receptor and a K-i > 10 muM for the AT, receptor is reported. Compound 21, with a bioavailability of 20-30% after oral administration and a half-life estimated to 4 h in rat, induces outgrowth of neurite cells, stimulates p42/p44(mapk), enhances in vivo duodenal alkaline secretion in Sprague-Dawley rats, and lowers the mean arterial blood pressure in anesthetized, spontaneously hypertensive rats. Thus, the peptidomimetic 21 exerts a similar biological response as the endogenous peptide angiotensin II after selective activation of the AT2 receptor. Compound 21, derived from the prototype nonselective AT(1)/AT(2) receptor agonist L-162,313 will serve as a valuable research tool, enabling studies of the function of the AT2 receptor in more detail.

  DOI：

  10.1021/jm049715t
• 作为产物：
  描述：

  5-异丁基-2-(N-叔丁基氨基磺酰基)噻吩-3-硼酸 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 caesium carbonate 、 1,2-二氨基环己烷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.67h， 生成 3-(4-imidazol-1-ylphenylmethyl)-5-isobutyl-N-tert-butylthiophene-2-sulfonamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of the First Selective Nonpeptide AT₂ Receptor Agonist

  摘要：

  The first druglike selective angiotensin II AT(2) receptor agonist (21) with a K-i value of 0.4 nM for the AT(2) receptor and a K-i > 10 muM for the AT, receptor is reported. Compound 21, with a bioavailability of 20-30% after oral administration and a half-life estimated to 4 h in rat, induces outgrowth of neurite cells, stimulates p42/p44(mapk), enhances in vivo duodenal alkaline secretion in Sprague-Dawley rats, and lowers the mean arterial blood pressure in anesthetized, spontaneously hypertensive rats. Thus, the peptidomimetic 21 exerts a similar biological response as the endogenous peptide angiotensin II after selective activation of the AT2 receptor. Compound 21, derived from the prototype nonselective AT(1)/AT(2) receptor agonist L-162,313 will serve as a valuable research tool, enabling studies of the function of the AT2 receptor in more detail.

  DOI：

  10.1021/jm049715t