3-<(4-Bromophenyl)methyl>-3H-imidazo<4,5-b>pyridine | 161529-30-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 3-<(4-Bromophenyl)methyl>-3H-imidazo<4,5-b>pyridine
• 英文别名: 3-(4-bromobenzyl)-3H-imidazo[4,5-b]pyridine；3-[(4-bromophenyl)methyl]imidazo[4,5-b]pyridine
• CAS: 161529-30-2
• 化学式: C₁₃H₁₀BrN₃
• 分子量: 288.147
• InChiKey: PCPHODWNHHPFJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-<(4-Bromophenyl)methyl>-3H-imidazo<4,5-b>pyridine 在 sodium hydroxide 、 四(三苯基膦)钯 、 苯甲醚 、 三氟乙酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 3.0h， 生成 3-[4-(Imidazo[4,5-b]pyridin-3-ylmethyl)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
• 作为产物：
  描述：

  对溴溴苄 、 N-(3-氨基-2-吡啶基)甲酰胺 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以49%的产率得到3-<(4-Bromophenyl)methyl>-3H-imidazo<4,5-b>pyridine
  参考文献：
  名称：

  Facile, Regioselective Syntheses of N-Alkylated 2,3-Diaminopyridines and Imidazo[4,5-b]pyridines

  摘要：

  Useful strategies are reported for the differentiation and selective synthetic manipulations of amino groups at the 2- and 3-positions of pyridines. It has been found that 2,3-diaminopyridine reacts with aldehydes under reductive amination conditions to give predominantly the N-3 alkylated products, which have been used for the regioselective synthesis of N-1 substituted imidazo[4,5-b]pyridines. Investigations using 2-formamido-3-aminopyridine (13), synthesized in two steps from 2-amino-3-nitropyridine, show it to be a versatile intermediate for the regioselective synthesis of either N-1 or N-3 substituted imidazo[4,5-b]pyridines, depending upon the conditions employed. The reductive amination of aldehydes with 13 using borane-pyridine in acetic acid affords the N-1 substituted imidazo[4,5-b]pyridines in one step, whereas reaction of 13 with alkyl halides in the presence of a suitable base (e.g., cesium carbonate) yields the N-3 substituted imidazo[4,5-b]pyridines. The generality of this synthetic methodology is noted.

  DOI：

  10.1021/jo00109a029

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.
• Facile, Regioselective Syntheses of N-Alkylated 2,3-Diaminopyridines and Imidazo[4,5-b]pyridines
  作者：Ish K. Khanna、Richard M. Weier、Kirk T. Lentz、Lydia Swenton、David C. Lankin

  DOI：10.1021/jo00109a029

  日期：1995.2

  Useful strategies are reported for the differentiation and selective synthetic manipulations of amino groups at the 2- and 3-positions of pyridines. It has been found that 2,3-diaminopyridine reacts with aldehydes under reductive amination conditions to give predominantly the N-3 alkylated products, which have been used for the regioselective synthesis of N-1 substituted imidazo[4,5-b]pyridines. Investigations using 2-formamido-3-aminopyridine (13), synthesized in two steps from 2-amino-3-nitropyridine, show it to be a versatile intermediate for the regioselective synthesis of either N-1 or N-3 substituted imidazo[4,5-b]pyridines, depending upon the conditions employed. The reductive amination of aldehydes with 13 using borane-pyridine in acetic acid affords the N-1 substituted imidazo[4,5-b]pyridines in one step, whereas reaction of 13 with alkyl halides in the presence of a suitable base (e.g., cesium carbonate) yields the N-3 substituted imidazo[4,5-b]pyridines. The generality of this synthetic methodology is noted.