N²-butylpyridine-2,6-diamine | 184965-19-3

• 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: N²-butylpyridine-2,6-diamine
• 英文别名: N~2~-Butylpyridine-2,6-diamine；6-N-butylpyridine-2,6-diamine
• CAS: 184965-19-3
• 化学式: C₉H₁₅N₃
• 分子量: 165.238
• InChiKey: OEUCXLDYSFNYGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N²-butylpyridine-2,6-diamine 、 4-烯丙氧基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以258 mg的产率得到4-(allyloxy)-N-(6-(butylamino)pyridin-2-yl)benzamide
  参考文献：
  名称：

  Discovery of benzamide analogs as negative allosteric modulators of human neuronal nicotinic receptors: Pharmacophore modeling and structure–activity relationship studies

  摘要：

  The present study describes our ongoing efforts toward the discovery of drugs that selectively target nAChR subtypes. We exploited knowledge on nAChR ligands and their binding site that were previously identified by our laboratory through virtual screenings and identified benzamide analogs as a novel chemical class of neuronal nicotinic receptor (nAChR) ligands. The lead molecule, compound 1 (4-(allyloxy)-N-(6-methylpyridin-2-yl)benzamide) inhibits nAChR activity with an IC50 value of 6.0 (3.4-10.6) mu M on human alpha 4 beta 2 nAChRs with a similar to 5-fold preference against human alpha 3 beta 4 nAChRs. Twenty-six analogs of compound 1 were also either synthesized or purchased for structure-activity relationship (SAR) studies and provided information relating the chemical/structural properties of the molecules to their ability to inhibit nAChR activity. The discovery of subtype-selective ligands of nAChRs described here should contribute significantly to our understanding of the involvement of specific nAChR subtypes in normal and pathophysiological states. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.03.082
• 作为产物：
  描述：

  2-氨基-6-溴吡啶 在 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三乙胺 、 sodium hydroxide 、 sodium t-butanolate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 生成 N²-butylpyridine-2,6-diamine
  参考文献：
  名称：

  Discovery of benzamide analogs as negative allosteric modulators of human neuronal nicotinic receptors: Pharmacophore modeling and structure–activity relationship studies

  摘要：

  The present study describes our ongoing efforts toward the discovery of drugs that selectively target nAChR subtypes. We exploited knowledge on nAChR ligands and their binding site that were previously identified by our laboratory through virtual screenings and identified benzamide analogs as a novel chemical class of neuronal nicotinic receptor (nAChR) ligands. The lead molecule, compound 1 (4-(allyloxy)-N-(6-methylpyridin-2-yl)benzamide) inhibits nAChR activity with an IC50 value of 6.0 (3.4-10.6) mu M on human alpha 4 beta 2 nAChRs with a similar to 5-fold preference against human alpha 3 beta 4 nAChRs. Twenty-six analogs of compound 1 were also either synthesized or purchased for structure-activity relationship (SAR) studies and provided information relating the chemical/structural properties of the molecules to their ability to inhibit nAChR activity. The discovery of subtype-selective ligands of nAChRs described here should contribute significantly to our understanding of the involvement of specific nAChR subtypes in normal and pathophysiological states. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.03.082

文献信息

• A PROCESS FOR PREPARING PYRIDINE-2,6-DIAMINES
  申请人：Akzo Nobel N.V.

  公开号：EP0825985A1

  公开（公告）日：1998-03-04
• US5939553A
  申请人：——

  公开号：US5939553A

  公开（公告）日：1999-08-17
• [EN] A PROCESS FOR PREPARING PYRIDINE-2,6-DIAMINES<br/>[FR] PROCEDE DE PREPARATION DE PYRIDINE-2,6-DIAMINES
  申请人：AKZO NOBEL N.V.

  公开号：WO1996036607A1

  公开（公告）日：1996-11-21

  (EN) A process has been found for preparing pyridine-2,6-diamines, i.e., 2,6-diaminopyridine (DAP) and derivative compounds in which one of the amino groups is a substituted amine (secondary or tertiary). According to this process, 3-hydroxy pentane 1,5-dinitrile (3-hydroxyglutaronitrile) is reacted with an ammonium donor in the form of ammonia, a primary amine such as n-butylamine, or a secondary amine such as piperidine.(FR) On a trouvé un procédé de préparation de pyridine-2,6-diamines, c'est-à-dire de 2,6-diaminopyridine (DAP) et de composés dérivés de celle-ci, dans lequel l'un des groupes amino est une amine (secondaire ou tertiaire) substituée, et consistant à faire réagir du 1,5-dinitrile de 3-hydroxy pentane (3-hydroxyglutaronitrile) avec un donneur d'ammonium sous la forme d'ammoniaque, avec une amine primaire, telle que n-butylamine, ou avec une amine secondaire telle que pipéridine.
• Discovery of benzamide analogs as negative allosteric modulators of human neuronal nicotinic receptors: Pharmacophore modeling and structure–activity relationship studies
  作者：Bitna Yi、Sihui Long、Tatiana F. González-Cestari、Brandon J. Henderson、Ryan E. Pavlovicz、Karl Werbovetz、Chenglong Li、Dennis B. McKay

  DOI：10.1016/j.bmc.2013.03.082

  日期：2013.8

  The present study describes our ongoing efforts toward the discovery of drugs that selectively target nAChR subtypes. We exploited knowledge on nAChR ligands and their binding site that were previously identified by our laboratory through virtual screenings and identified benzamide analogs as a novel chemical class of neuronal nicotinic receptor (nAChR) ligands. The lead molecule, compound 1 (4-(allyloxy)-N-(6-methylpyridin-2-yl)benzamide) inhibits nAChR activity with an IC50 value of 6.0 (3.4-10.6) mu M on human alpha 4 beta 2 nAChRs with a similar to 5-fold preference against human alpha 3 beta 4 nAChRs. Twenty-six analogs of compound 1 were also either synthesized or purchased for structure-activity relationship (SAR) studies and provided information relating the chemical/structural properties of the molecules to their ability to inhibit nAChR activity. The discovery of subtype-selective ligands of nAChRs described here should contribute significantly to our understanding of the involvement of specific nAChR subtypes in normal and pathophysiological states. (C) 2013 Published by Elsevier Ltd.