N-n-butyl-3-methoxypyridin-2(1H)-one | 181431-47-0

• 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-n-butyl-3-methoxypyridin-2(1H)-one
• 英文别名: 3-methoxy-1-butyl-2(1H)-pyridinone；1-butyl-3-methoxy-2(1H)-pyridone；1-butyl-3-methoxy-2-pyridone；1-butyl-3-methoxypyridin-2-one
• CAS: 181431-47-0
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: OQYDXGOHEQYDSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-n-butyl-3-methoxypyridin-2(1H)-one 在 劳森试剂 、 吡啶盐酸盐 、 碘甲烷 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 30.5h， 生成 N-n-butyl-3-hydroxy-4-methylpyridine-2(1H)-thione
  参考文献：
  名称：

  Design, synthesis, and binding mode prediction of 2-pyridone-based selective CB2 receptor agonists

  摘要：

  Selective CB2 agonists have the potential for treating pain without central CBI-mediated adverse effects. Screening efforts identified 1,2-dihydro-3-isoquinolone 1; however, this compound has the drawbacks of being difficult to synthesize with two asymmetric carbons on an isoquinolone scaffold and of having a highly lipophilic physicochemical property. To address these two major problems, we designed the 2-pyridone-based lead 15a, which showed moderate affinity for CB2. Optimization of 15a led to identification of 39f with high affinity for CB2 and selectivity over CBI. Prediction of the binding mode of 39f in complex with an active-state CB2 homology model provided structural insights into its high affinity for CB2. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.006
• 作为产物：
  描述：

  1-碘丁烷 在 sodium hydride 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 1.0h， 以93%的产率得到N-n-butyl-3-methoxypyridin-2(1H)-one
  参考文献：
  名称：

  ANTIPRURITICS

  摘要：

  公开号：

  EP1477186B1

文献信息

• Synthesis, Physicochemical Properties, and Biological Evaluation of Hydroxypyranones and Hydroxypyridinones:  Novel Bidentate Ligands for Cell-Labeling
  作者：Beverley L. Ellis、Anne K. Duhme、Robert C. Hider、M. Bilayet Hossain、Safia Rizvi、Dick van der Helm

  DOI：10.1021/jm960220g

  日期：1996.1.1

  The synthesis of a range of hydroxypyranones and hydroxypyridinones with potential for the chelation of indium(III) is described. The crystal structures of two of the indium complexes are presented. The distribution coefficients of the ligands and the corresponding iron(III), gallium(III), and indium(III) complexes are reported. Good linear relationships between the distribution coefficients of the

  描述了一系列可能与铟（III）螯合的羟基吡喃酮和羟基吡啶酮。给出了两种铟配合物的晶体结构。报告了配体和相应的铁（III），镓（III）和铟（III）配合物的分布系数。在铁和镓配合物与铁和铟配合物的分布系数之间获得了良好的线性关系。相反，在游离配体的分布系数与三组配合物的分布系数之间获得了非线性关系。后一种关系用于鉴定具有最佳细胞标记特性的化合物。已经将两种这样的化合物（6-（烷氧基甲基）-3-羟基-4H-吡喃-4-酮）与托酚酮比较了它们用111 In标记人白细胞的能力。所选配体的白细胞标记效率更高，体外血浆稳定性与111In-对羟基苯甲酸类似。这些结果表明，新的双齿配体可能比目前用于细胞标记的配体具有优势。
• Antipruritics
  申请人：Yasui Kiyoshi

  公开号：US20050101590A1

  公开（公告）日：2005-05-12

  It is intended to provide antipruritics (drugs to control itching, antiitch agents and drugs to stop itching). It is found out that a compound having an agonistic activity to the cannabinoid receptor shows an antipruritics effect.

  这意味着它旨在提供止痒药（用于控制瘙痒的药物，抗瘙痒剂和止痒药）。研究发现，具有激动性作用的大麻素受体的化合物具有止痒效果。
• Pyridone derivatives having affinity for cannabinoid 2-type receptor
  申请人：——

  公开号：US20040082619A1

  公开（公告）日：2004-04-29

  It was found that the compound having a binding activity to the cannabinoid type 2 receptor represented by the formula (I): 1 wherein R 1 is a group represented by the formula: —Y 1 —Y 2 —Y 3 —R a wherein Y 1 is single bond or the like; Y 2 is —C(═O)—NH— or the like; Y 3 is optionally substituted aryl or the like; R 2 is hydrogen or the like; R 3 is alkyl or the like; R 4 is alkyl or the like; R 5 is optionally substituted alkyl or the like; or R 3 and R 4 taken together with the adjacent atom form cyclic group or the like.

  发现具有与cannabinoid 2型受体结合活性的化合物，其代表式为（I）：1其中R1是由式表示的基团：—Y1—Y2—Y3—Ra其中Y1是单键或类似物；Y2是—C(═O)—NH—或类似物；Y3是可选取代芳基或类似物；R2是氢或类似物；R3是烷基或类似物；R4是烷基或类似物；R5是可选取代烷基或类似物；或R3和R4与相邻原子结合形成环状基团或类似物。
• Pyridone derivatives having a binding activity to the cannabinoid type 2 receptor
  申请人：Tada Yukio

  公开号：US20060052411A1

  公开（公告）日：2006-03-09

  It was found that the compound having a binding activity to the cannabinoid type 2 receptor represented by the formula (I): wherein R 1 is a group represented by the formula: —Y 1 —Y 2 —Y 3 —R a wherein Y 1 is single bond or the like; Y 2 is —C(═O)—NH— or the like; Y 3 is optionally substituted aryl or the like; R 2 is hydrogen or the like; R 3 is alkyl or the like; R 4 is alkyl or the like; R 5 is optionally substituted alkyl or the like; or R 3 and R 4 taken together with the adjacent atom form cyclic group or the like.

  被发现的化合物具有与cannabinoid type 2 受体结合活性，其化学式为(I)，其中R1是由公式表示的基团：—Y1—Y2—Y3—Ra，其中Y1是单键或类似物；Y2是—C(═O)—NH—或类似物；Y3是可选择取代的芳基或类似物；R2是氢或类似物；R3是烷基或类似物；R4是烷基或类似物；R5是可选择取代的烷基或类似物；或R3和R4与相邻原子一起形成环状基团或类似物。
• Pyridone derivatives having a binding activity to the cannabinoid type 2 recepter
  申请人：TADA Yukio

  公开号：US20100081686A1

  公开（公告）日：2010-04-01

  It was found that the compound having a binding activity to the cannabinoid type 2 receptor represented by the formula (I): wherein R 1 is a group represented by the formula: —Y 1 —Y 2 —Y 3 —R a wherein Y 1 is single bond or the like; Y 2 is —C(═O)—NH— or the like; Y 3 is optionally substituted aryl or the like; R 2 is hydrogen or the like; R 3 is alkyl or the like; R 4 is alkyl or the like; R 5 is optionally substituted alkyl or the like; or R 3 and R 4 taken together with the adjacent atom form cyclic group or the like.

  发现化合物具有与cannabinoid type 2受体结合活性，该化合物的公式为（I）：其中R1是由公式表示的基团：—Y1—Y2—Y3—Ra，其中Y1是单键或类似物；Y2是—C（═O）—NH—或类似物；Y3是可选择的取代芳基或类似物；R2是氢或类似物；R3是烷基或类似物；R4是烷基或类似物；R5是可选择的取代烷基或类似物；或R3和R4与相邻原子结合形成环状基团或类似物。