(S)-3-dimethylamino-butan-1-ol | 1088884-57-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-3-dimethylamino-butan-1-ol
• 英文别名: (3S)-3-(dimethylamino)butan-1-ol
• CAS: 1088884-57-4
• 化学式: C₆H₁₅NO
• mdl: MFCD09971253
• 分子量: 117.191
• InChiKey: QTTKJYGPXLCJNF-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-甲基氮杂环丁烷盐酸盐 、 (S)-3-dimethylamino-butan-1-ol 、 N,N'-羰基二咪唑 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲苯 、 水 为溶剂， 反应 4.0h， 生成 (S)-3-((3-Methylazetidine-1-carbonyloxy)-1-methylpropyl)dimethylammonium Oxalate
  参考文献：
  名称：

  Novel Acetylcholine and Carbamoylcholine Analogues: Development of a Functionally Selective α₄β₂ Nicotinic Acetylcholine Receptor Agonist

  摘要：

  A series of carbamoylcholine and acetylcholine analogues were synthesized and characterized pharmacologically at neuronal nicotinic acetylcholine receptors (nAChRs). Several of the compounds displayed low nanomolar binding affinities to the alpha(4)beta(2) nAChR and pronounced selectivity for this subtype over alpha(3)beta(4), alpha(4)beta(4), and alpha(7) nAChRs. The high nAChR activity of carbamoylcholine analogue 5d was found to reside in its R-enantiomer, a characteristic most likely true for all other compounds in the series. Interestingly, the pronounced alpha(4)beta(2) selectivities exhibited by some of the compounds in the binding assays translated into functional selectivity. Compound 5a was a fairly potent partial alpha(4)beta(2) nAChR agonist with negligible activities at the alpha(3)beta(4) and alpha(7) subtypes, thus being one of the few truly functionally selective alpha(4)beta(2) nAChR agonists published to date. Ligand-protein docking experiments using homology models of the amino-terminal domains of alpha(4)beta(2) and alpha(3)beta(4) nAChRs identified residues Val 111(beta(2))/Ile 113(beta(4)), Phe 119(beta(2))/Gln 121(beta(4)), and Thr155(alpha(4))/Ser 150(alpha(3)) as possible key determinants of the alpha(4)beta(2)/alpha(3)beta(4)-selectivity displayed by the analogues. 4

  DOI：

  10.1021/jm701625v
• 作为产物：
  描述：

  聚合甲醛 、 (S)-3-氨基丁醇 在 三乙酰氧基硼氢化钠 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以63%的产率得到(S)-3-dimethylamino-butan-1-ol
  参考文献：
  名称：

  Novel Acetylcholine and Carbamoylcholine Analogues: Development of a Functionally Selective α₄β₂ Nicotinic Acetylcholine Receptor Agonist

  摘要：

  A series of carbamoylcholine and acetylcholine analogues were synthesized and characterized pharmacologically at neuronal nicotinic acetylcholine receptors (nAChRs). Several of the compounds displayed low nanomolar binding affinities to the alpha(4)beta(2) nAChR and pronounced selectivity for this subtype over alpha(3)beta(4), alpha(4)beta(4), and alpha(7) nAChRs. The high nAChR activity of carbamoylcholine analogue 5d was found to reside in its R-enantiomer, a characteristic most likely true for all other compounds in the series. Interestingly, the pronounced alpha(4)beta(2) selectivities exhibited by some of the compounds in the binding assays translated into functional selectivity. Compound 5a was a fairly potent partial alpha(4)beta(2) nAChR agonist with negligible activities at the alpha(3)beta(4) and alpha(7) subtypes, thus being one of the few truly functionally selective alpha(4)beta(2) nAChR agonists published to date. Ligand-protein docking experiments using homology models of the amino-terminal domains of alpha(4)beta(2) and alpha(3)beta(4) nAChRs identified residues Val 111(beta(2))/Ile 113(beta(4)), Phe 119(beta(2))/Gln 121(beta(4)), and Thr155(alpha(4))/Ser 150(alpha(3)) as possible key determinants of the alpha(4)beta(2)/alpha(3)beta(4)-selectivity displayed by the analogues. 4

  DOI：

  10.1021/jm701625v

文献信息

• Novel Acetylcholine and Carbamoylcholine Analogues: Development of a Functionally Selective α₄β₂ Nicotinic Acetylcholine Receptor Agonist
  作者：Camilla P. Hansen、Anders A. Jensen、Jeppe K. Christensen、Thomas Balle、Tommy Liljefors、Bente Frølund

  DOI：10.1021/jm701625v

  日期：2008.12.11

  A series of carbamoylcholine and acetylcholine analogues were synthesized and characterized pharmacologically at neuronal nicotinic acetylcholine receptors (nAChRs). Several of the compounds displayed low nanomolar binding affinities to the alpha(4)beta(2) nAChR and pronounced selectivity for this subtype over alpha(3)beta(4), alpha(4)beta(4), and alpha(7) nAChRs. The high nAChR activity of carbamoylcholine analogue 5d was found to reside in its R-enantiomer, a characteristic most likely true for all other compounds in the series. Interestingly, the pronounced alpha(4)beta(2) selectivities exhibited by some of the compounds in the binding assays translated into functional selectivity. Compound 5a was a fairly potent partial alpha(4)beta(2) nAChR agonist with negligible activities at the alpha(3)beta(4) and alpha(7) subtypes, thus being one of the few truly functionally selective alpha(4)beta(2) nAChR agonists published to date. Ligand-protein docking experiments using homology models of the amino-terminal domains of alpha(4)beta(2) and alpha(3)beta(4) nAChRs identified residues Val 111(beta(2))/Ile 113(beta(4)), Phe 119(beta(2))/Gln 121(beta(4)), and Thr155(alpha(4))/Ser 150(alpha(3)) as possible key determinants of the alpha(4)beta(2)/alpha(3)beta(4)-selectivity displayed by the analogues. 4