2-methyl-3-(3-nitrophenyl)pyridine | 52583-59-2

• 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-methyl-3-(3-nitrophenyl)pyridine
• 英文别名: 3-m-Nitrophenyl-2-picolin
• CAS: 52583-59-2
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: RYNNJTPAGWSIKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(3-nitrophenyl)pyridine 在 盐酸 、 tin(ll) chloride 作用下， 生成 3-(2-methyl-3-pyridyl)aniline
  参考文献：
  名称：

  Biarylcarbamoylindolines Are Novel and Selective 5-HT_2C Receptor Inverse Agonists:  Identification of 5-Methyl-1-[[2-[(2-methyl-3-pyridyl)oxy]- 5-pyridyl]carbamoyl]-6-trifluoromethylindoline (SB-243213) as a Potential Antidepressant/Anxiolytic Agent

  摘要：

  The evolution, synthesis, and biological activity of a novel series of 5-HT2C receptor inverse agonists are reported. Biarylcarbamoylindolines have been identified with excellent 5-HT2C affinity and selectivity over 5-HT2A receptors. In addition, (pyridyloxypyridyl)carbamoylindolines have been discovered with additional selectivity over the closely related 5-HT2B receptor. Compounds from this series are inverse agonists at the human cloned 5-HT2C receptor, completely abolishing basal activity in a functional assay. The new series have reduced P450 inhibitory liability compared to a previously described series of 1-(3-pyridylcarbamoyl)indolines (Bromidge et al. J. Med. Chem. 1998, 41, 1598) from which they evolved. Compounds from this series showed excellent oral activity in a rat mCPP hypolocomotion model and in animal models of anxiety. On the basis of their favorable biological profile, 32 (SB-228357) and 40 (SB-243213) have been selected for further evaluation to determine their therapeutic potential for the treatment of CNS disorders such as depression and anxiety.

  DOI：

  10.1021/jm990388c
• 作为产物：
  描述：

  2-甲基-3-苯基吡啶 在 硫酸 、 硝酸 作用下， 反应 3.0h， 以35%的产率得到2-methyl-3-(4-nitrophenyl)pyridine
  参考文献：
  名称：

  硝基苯基吡啶的合成及杀菌活性

  摘要：

  本通讯中提供了有关新的取代硝基苯基吡啶的制备及其杀真菌活性的数据，以及我们之前合成的一些二和三烷基取代的硝基苯基吡啶的活性 [5]。这是对吡啶衍生物的合成和杀真菌特性的研究 [2-4] 的延续。通过硝化 3-甲基-2-苯基吡啶 (I)、3-甲基-4-苯基吡啶 (V) 和 2-甲基-3-苯基吡啶 (IX) [6, 8] 得到以下新化合物： 3-甲基-2-(4-硝基苯基)吡啶 (II), 3-甲基-2-(3-硝基苯基)吡啶 (III), 3-甲基-4-(4-硝基苯基)吡啶 (VI), 2-甲基-3 -(4-硝基苯基)吡啶(X)和2-甲基-3-(3-硝基苯基)-2-甲基吡啶(XI)。

  DOI：

  10.1007/bf00819968