3-[4-[(2-Ethylbenzimidazol-1-yl)methyl]phenyl]-5-(2-methylpropyl)thiophene-2-sulfonamide | 575465-32-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 3-[4-[(2-Ethylbenzimidazol-1-yl)methyl]phenyl]-5-(2-methylpropyl)thiophene-2-sulfonamide
• CAS: 575465-32-6
• 化学式: C₂₄H₂₇N₃O₂S₂
• 分子量: 453.629
• InChiKey: DZHPAHHEUIWTPA-UHFFFAOYSA-N

物化性质

• 沸点：
  657.5±65.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氯甲酸丁酯 、 3-[4-[(2-Ethylbenzimidazol-1-yl)methyl]phenyl]-5-(2-methylpropyl)thiophene-2-sulfonamide 在 吡啶 、 2-(吡咯烷-1-基)吡啶 作用下， 以47.6 mg的产率得到butyl N-[3-[4-[(2-ethylbenzimidazol-1-yl)methyl]phenyl]-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：

  2-乙基苯并咪唑 在 氢氧化钾 、 sodium hydroxide 、 四(三苯基膦)钯 、 苯甲醚 、 三氟乙酸 作用下， 以 乙醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 6.0h， 生成 3-[4-[(2-Ethylbenzimidazol-1-yl)methyl]phenyl]-5-(2-methylpropyl)thiophene-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

文献信息

• Design, Synthesis, and Biological Evaluation of the First Selective Nonpeptide AT₂ Receptor Agonist
  作者：Yiqian Wan、Charlotta Wallinder、Bianca Plouffe、Hélène Beaudry、A. K. Mahalingam、Xiongyu Wu、Berndt Johansson、Mathias Holm、Milad Botoros、Anders Karlén、Anders Pettersson、Fred Nyberg、Lars Fändriks、Nicole Gallo-Payet、Anders Hallberg、Mathias Alterman

  DOI：10.1021/jm049715t

  日期：2004.11.1

  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.