2-(6-tert-butoxy-3-nitro-2-pyridyl)acetonitrile | 127792-76-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-(6-tert-butoxy-3-nitro-2-pyridyl)acetonitrile
• 英文别名: 2-[6-[(2-Methylpropan-2-yl)oxy]-3-nitropyridin-2-yl]acetonitrile
• CAS: 127792-76-1
• 化学式: C₁₁H₁₃N₃O₃
• 分子量: 235.243
• InChiKey: ZMZPGYKSWPFVAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  91.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(6-tert-butoxy-3-nitro-2-pyridyl)acetonitrile 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 2-(3-amino-6-t-butoxypyrid-2-yl)acetonitrile
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-5-硝基吡啶 在 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 56.0h， 生成 2-(6-tert-butoxy-3-nitro-2-pyridyl)acetonitrile
  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 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：——
• 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
  作者：John E. Macor、Carol A. Burkhart、James H. Heym、Jeffrey L. Ives、Lorraine A. Lebel、Michael E. Newman、Jann A. Nielsen、Kevin Ryan、David W. Schulz

  DOI：10.1021/jm00170a007

  日期：1990.8

  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.
• 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：——