5-tert-butoxy-3-<4-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridyl>pyrrolo<3,2-b>pyridine | 127792-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 5-tert-butoxy-3-<4-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridyl>pyrrolo<3,2-b>pyridine
• 英文别名: 3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)pyrrolo<3,2-b>pyridine；1(2H)-Pyridinecarboxylic acid, 4-[5-(1,1-dimethylethoxy)-1H-pyrrolo[3,2-b]pyridin-3-yl]-3,6-dihydro-, 1,1-dimethylethyl ester；tert-butyl 4-[5-[(2-methylpropan-2-yl)oxy]-1H-pyrrolo[3,2-b]pyridin-3-yl]-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 127792-78-3
• 化学式: C₂₁H₂₉N₃O₃
• 分子量: 371.48
• InChiKey: OSZKBTVGZKFRKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  67.45
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-tert-butoxy-3-<4-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridyl>pyrrolo<3,2-b>pyridine 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以0.70 g的产率得到CP93129二盐酸盐
  参考文献：
  名称：

  3-(1,2,5,6-Tetrahydropyrid-4-yl)pyrrolo[3,2-b]pyrid-5-one: a potent and selective serotonin (5-HT1*) agonist and rotationally restricted phenolic analog of 5-methoxy-3-(1,2,5,6-tetrahydropyrid-4-yl)indole

  摘要：

  The synthesis and in vitro and in vivo characteristics of 3-(1,2,5,6-tetrahydropyrid-4-yl)pyrrolo[3,2-b]pyrid-5-one (1, CP-93,129) are described. This rotationally restricted phenolic analogue of RU-24,969 is a potent (15 nM) and selective (200x vs the 5-HT1A receptor, 150x vs the 5HT1D receptor) functional agonist for the 5-HT1B receptor. Direct infusion of 1 into the paraventricular nucleus of the hypothalamus of rats significantly inhibits food intake, implicating the role of 5-HT1B receptors in regulating feeding behavior in rodents. 3-(1,2,5,6-Tetrahydropyrid-4-yl)pyrrolo[3,2-b]pyrid-5-one (1) has also been shown to be biochemically discriminatory in its ability to selectively inhibit forskolin-stimulated adenylate cyclase activity only at the 5-HT1B receptor. The source of the selectivity of 1 appears to lie in the ability of a pyrrolo[3,2-b]pyrid-5-one to act as a rotationally restricted bioisosteric replacement for 5-hydroxyindole.

  DOI：

  10.1021/jm00170a007
• 作为产物：
  描述：

  2-氯-5-硝基吡啶 在 palladium on activated charcoal potassium tert-butylate 、 氢气 、 sodium 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， -10.0~60.0 ℃ 、303.98 kPa 条件下， 反应 65.0h， 生成 5-tert-butoxy-3-<4-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridyl>pyrrolo<3,2-b>pyridine
  参考文献：
  名称：

  3-(1,2,5,6-Tetrahydropyrid-4-yl)pyrrolo[3,2-b]pyrid-5-one: a potent and selective serotonin (5-HT1*) agonist and rotationally restricted phenolic analog of 5-methoxy-3-(1,2,5,6-tetrahydropyrid-4-yl)indole

  摘要：

  The synthesis and in vitro and in vivo characteristics of 3-(1,2,5,6-tetrahydropyrid-4-yl)pyrrolo[3,2-b]pyrid-5-one (1, CP-93,129) are described. This rotationally restricted phenolic analogue of RU-24,969 is a potent (15 nM) and selective (200x vs the 5-HT1A receptor, 150x vs the 5HT1D receptor) functional agonist for the 5-HT1B receptor. Direct infusion of 1 into the paraventricular nucleus of the hypothalamus of rats significantly inhibits food intake, implicating the role of 5-HT1B receptors in regulating feeding behavior in rodents. 3-(1,2,5,6-Tetrahydropyrid-4-yl)pyrrolo[3,2-b]pyrid-5-one (1) has also been shown to be biochemically discriminatory in its ability to selectively inhibit forskolin-stimulated adenylate cyclase activity only at the 5-HT1B receptor. The source of the selectivity of 1 appears to lie in the ability of a pyrrolo[3,2-b]pyrid-5-one to act as a rotationally restricted bioisosteric replacement for 5-hydroxyindole.

  DOI：

  10.1021/jm00170a007

文献信息

• Macor, John E.; Newman, Michael E., Heterocycles, 1990, vol. 31, # 5, p. 805 - 809
  作者：Macor, John E.、Newman, Michael E.

  DOI：——

  日期：——
• MACOR, JOHN E.;NEWMAN, MICHAEL H., HETEROCYCLES, 31,(1990) N, C. 805-809
  作者：MACOR, JOHN E.、NEWMAN, MICHAEL H.

  DOI：——

  日期：——
• MACOR, JOHN E.;BURKHART, CAROL A.;HEYM, JAMES H.;IVES, JEFFREY L.;LEBEL, +, J. MED. CHEM., 33,(1990) N, C. 2087-2093
  作者：MACOR, JOHN E.、BURKHART, CAROL A.、HEYM, JAMES H.、IVES, JEFFREY L.、LEBEL, +

  DOI：——

  日期：——