2-(butylamino)-6-bromopyridine | 1289269-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(butylamino)-6-bromopyridine
• 英文别名: 6-bromo-N-butylpyridin-2-amine
• CAS: 1289269-76-6
• 化学式: C₉H₁₃BrN₂
• 分子量: 229.12
• InChiKey: WMAXNBQDKMMQND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(butylamino)-6-bromopyridine 在 四(三苯基膦)钯 、 碳酸氢钠 、 一水合肼 作用下， 以 乙二醇二甲醚 、 乙醇 、 氯仿 、 水 为溶剂， 反应 28.0h， 生成 3-(4-chlorophenyl)-1-{3-[6-(butylamino)pyridin-2-yl]phenyl}urea
  参考文献：
  名称：

  Diarylureas as Allosteric Modulators of the Cannabinoid CB1 Receptor: Structure–Activity Relationship Studies on 1-(4-Chlorophenyl)-3-{3-[6-(pyrrolidin-1-yl)pyridin-2-yl]phenyl}urea (PSNCBAM-1)

  摘要：

  The recent discovery of allosteric modulators of the CB1 receptor including PSNCBAM-1 (4) has generated significant interest in CB1 receptor allosteric modulation. Here in the first SAR study on 4, we have designed and synthesized a series of analogs focusing on modifications at two positions. Pharmacological evaluation in calcium mobilization and binding assays revealed the importance of alkyl substitution at the 2-aminopyridine moiety and electron deficient aromatic groups at the 4-chlorophenyl position for activity at the CB1 receptor, resulting in several analogs with comparable potency to 4. These compounds increased the specific binding of [H-3]CP55,940, in agreement with previous reports. Importantly, 4 and two analogs dose-dependently reduced the E-max. of the agonist curve in the CB1 calcium mobilization assays, confirming their negative allosteric modulator characteristics. Given the side effects associated with CB1 receptor orthosteric antagonists, negative allosteric modulators provide an alternative approach to modulate the pharmacologically important CB1 receptor.

  DOI：

  10.1021/jm501042u
• 作为产物：
  描述：

  2,6-二溴吡啶 、 正丁胺 在 三乙胺 作用下， 以 水 为溶剂， 反应 23.0h， 以96%的产率得到2-(butylamino)-6-bromopyridine
  参考文献：
  名称：

  Convenient Synthesis of Aminopyridinecarboxylic Acids

  摘要：

  6-(Alkylamino)pyridine-2-carboxylic acids and 5-(alkylamino)pyridine-3-carboxylic acids were conveniently synthesized from dibromopyridine in satisfactory yields.

  DOI：

  10.3987/com-11-12290

文献信息

• Diarylureas as Allosteric Modulators of the Cannabinoid CB1 Receptor: Structure–Activity Relationship Studies on 1-(4-Chlorophenyl)-3-{3-[6-(pyrrolidin-1-yl)pyridin-2-yl]phenyl}urea (PSNCBAM-1)
  作者：Nadezhda German、Ann M. Decker、Brian P. Gilmour、Elaine A. Gay、Jenny L. Wiley、Brian F. Thomas、Yanan Zhang

  DOI：10.1021/jm501042u

  日期：2014.9.25

  The recent discovery of allosteric modulators of the CB1 receptor including PSNCBAM-1 (4) has generated significant interest in CB1 receptor allosteric modulation. Here in the first SAR study on 4, we have designed and synthesized a series of analogs focusing on modifications at two positions. Pharmacological evaluation in calcium mobilization and binding assays revealed the importance of alkyl substitution at the 2-aminopyridine moiety and electron deficient aromatic groups at the 4-chlorophenyl position for activity at the CB1 receptor, resulting in several analogs with comparable potency to 4. These compounds increased the specific binding of [H-3]CP55,940, in agreement with previous reports. Importantly, 4 and two analogs dose-dependently reduced the E-max. of the agonist curve in the CB1 calcium mobilization assays, confirming their negative allosteric modulator characteristics. Given the side effects associated with CB1 receptor orthosteric antagonists, negative allosteric modulators provide an alternative approach to modulate the pharmacologically important CB1 receptor.
• Convenient Synthesis of Aminopyridinecarboxylic Acids
  作者：Iwao Okamoto、Masayuki Terashima、Rempei Yoshioka、Tomonori Muramatsu、Satomi Kojima、Haruka Inoue、Mio Takahashi、Nobuyoshi Morita、Osamu Tamura

  DOI：10.3987/com-11-12290

  日期：——

  6-(Alkylamino)pyridine-2-carboxylic acids and 5-(alkylamino)pyridine-3-carboxylic acids were conveniently synthesized from dibromopyridine in satisfactory yields.