N-(4-hydroxybutyl)picolinamide

• 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: N-(4-hydroxybutyl)picolinamide
• 英文别名: N-(4-hydroxybutyl)pyridine-2-carboxamide
• 化学式: C₁₀H₁₄N₂O₂
• 分子量: 194.233
• InChiKey: PGGHLQIULRHUAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-hydroxybutyl)picolinamide 在 四溴化碳 、 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成 N-(4-(4-(6-methylpyridin-2-yl)piperazin-1-yl)butyl)picolinamide
  参考文献：
  名称：

  Targeting Dopamine D₃ and Serotonin 5-HT_1A and 5-HT_2A Receptors for Developing Effective Antipsychotics: Synthesis, Biological Characterization, and Behavioral Studies

  摘要：

  Combination of dopamine D-3 antagonism, serotonin 5-HT1A partial agonism, and antagonism at 5-HT2A leads to a novel approach to potent atypical antipsychotics. Exploitation of the original structureactivity relationships resulted in the identification of safe and effective antipsychotics devoid of extrapyramidal symptoms liability, sedation, and catalepsy. The potential atypical antipsychotic 5bb was selected for further pharmacological investigation. The distribution of c-fos positive cells in the ventral striatum confirmed the atypical antipsychotic profile of 5bb in agreement with behavioral rodent studies. 5bb administered orally demonstrated a biphasic effect on the MK801-induced hyperactivity at dose levels not able to induce sedation, catalepsy, or learning impairment in passive avoidance. In microdialysis studies, 5bb increased the dopamine efflux in the medial prefrontal cortex. Thus, 5bb represents a valuable lead for the development of atypical antipsychotics endowed with a unique pharmacological profile for addressing negative symptoms and cognitive deficits in schizophrenia.

  DOI：

  10.1021/jm501119j
• 作为产物：
  描述：

  2-吡啶甲酸 、 4-氨基-1-丁醇 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到N-(4-hydroxybutyl)picolinamide
  参考文献：
  名称：

  Palladium-catalyzed picolinamide-directed coupling of C(sp²)–H and C(sp²)–H: a straightforward approach to quinolinone and pyridone scaffolds

  摘要：

  使用钯催化的吡啶酰胺定向偶联C(sp²)–H和C(sp²)–H的方法，形成了六元环杂环化合物奎诺啉酮和吡啶酮，这是前所未有的。

  DOI：

  10.1039/c5cc00298b

文献信息

• Targeting Dopamine D₃ and Serotonin 5-HT_1A and 5-HT_2A Receptors for Developing Effective Antipsychotics: Synthesis, Biological Characterization, and Behavioral Studies
  作者：Margherita Brindisi、Stefania Butini、Silvia Franceschini、Simone Brogi、Francesco Trotta、Sindu Ros、Alfredo Cagnotto、Mario Salmona、Alice Casagni、Marco Andreassi、Simona Saponara、Beatrice Gorelli、Pia Weikop、Jens D. Mikkelsen、Jorgen Scheel-Kruger、Karin Sandager-Nielsen、Ettore Novellino、Giuseppe Campiani、Sandra Gemma

  DOI：10.1021/jm501119j

  日期：2014.11.26

  Combination of dopamine D-3 antagonism, serotonin 5-HT1A partial agonism, and antagonism at 5-HT2A leads to a novel approach to potent atypical antipsychotics. Exploitation of the original structureactivity relationships resulted in the identification of safe and effective antipsychotics devoid of extrapyramidal symptoms liability, sedation, and catalepsy. The potential atypical antipsychotic 5bb was selected for further pharmacological investigation. The distribution of c-fos positive cells in the ventral striatum confirmed the atypical antipsychotic profile of 5bb in agreement with behavioral rodent studies. 5bb administered orally demonstrated a biphasic effect on the MK801-induced hyperactivity at dose levels not able to induce sedation, catalepsy, or learning impairment in passive avoidance. In microdialysis studies, 5bb increased the dopamine efflux in the medial prefrontal cortex. Thus, 5bb represents a valuable lead for the development of atypical antipsychotics endowed with a unique pharmacological profile for addressing negative symptoms and cognitive deficits in schizophrenia.
• Palladium-catalyzed picolinamide-directed coupling of C(sp²)–H and C(sp²)–H: a straightforward approach to quinolinone and pyridone scaffolds
  作者：Dengyou Zhang、Feng Gao、Yong Nian、Yu Zhou、Hualiang Jiang、Hong Liu

  DOI：10.1039/c5cc00298b

  日期：——

  An unprecedented palladium-catalyzed picolinamide-directed coupling of C(sp²)–H and C(sp²)–H has been developed with exclusive formation of the six-membered ring heterocyclics – quinolinone and pyridone.

  使用钯催化的吡啶酰胺定向偶联C(sp²)–H和C(sp²)–H的方法，形成了六元环杂环化合物奎诺啉酮和吡啶酮，这是前所未有的。