N-benzyl-1-butyl-6-ethyl-5-methyl-2-oxopyridine-3-carboxamide | 441303-63-5

• 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-benzyl-1-butyl-6-ethyl-5-methyl-2-oxopyridine-3-carboxamide
• CAS: 441303-63-5
• 化学式: C₂₀H₂₆N₂O₂
• 分子量: 326.439
• InChiKey: ZKAMYFKSRGZWDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-butylpentan-3-imine 在 氯化亚砜 、 水 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 二乙二醇二甲醚 、 甲苯 为溶剂， 反应 5.5h， 生成 N-benzyl-1-butyl-6-ethyl-5-methyl-2-oxopyridine-3-carboxamide
  参考文献：
  名称：

  Selective CB2 agonists with anti-pruritic activity: Discovery of potent and orally available bicyclic 2-pyridones

  摘要：

  The CB2 receptor has emerged as a potential target for the treatment of pruritus as well as pain without CB1-mediated side effects. We previously identified 2-pyridone derivatives 1 and 2 as potent CB2 agonists; however, this series of compounds was found to have unacceptable pharmacokinetic profiles with no significant effect in vivo. To improve these profiles, we performed further structural optimization of 1 and 2, which led to the discovery of bicyclic 2-pyridone 18e with improved CB2 affinity and selectivity over CB1. In a mouse pruritus model, 18e inhibited compound 48/80 induced scratching behavior at a dose of 100 mg/kg. In addition, the docking model of 18e with an active-state CB2 homology model indicated the structural basis of its high affinity and selectivity over CB1. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.03.030

文献信息

• Antipruritics
  申请人：Yasui Kiyoshi

  公开号：US20080312292A1

  公开（公告）日：2008-12-18

  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.

  这句话的意思是：它旨在提供止痒药（控制瘙痒的药物、抗瘙痒剂和止痒药物）。发现一种具有类脂激素受体激动活性的化合物具有止痒效果。
• 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。
• Novel use of cannabinoid receptor agonist
  申请人：Arimura Akinori

  公开号：US20070027144A1

  公开（公告）日：2007-02-01

  An inhibitor for an inflammatory cell infiltration in the respiratory tract, an inhibitor for hyperirritability in the respiratory tract, a muciparous inhibitor, or a bronchodilator which contains as an active ingredient a compound represented by the formula (I) or (II): wherein R 1 is the group represented by the formula: —C(=Z)-W—R 4 wherein Z is an oxygen atom or the like; W is an oxygen atom or the like; R 4 is optionally substituted alkyl or the like; R 2 and R 3 are independently optionally substituted alkyl or the like; or R 2 and R 3 are taken together to form optionally substituted alkylene which may contain a heteroatom(s); m is an integer of 0 to 2; A is optionally substituted aryl or optionally substituted heteroaryl; wherein R 5 is the group represented by the formula: —Y 1 —Y 2 —Y 3 —R a wherein Y 1 and Y 3 are each independently a bond or the like; Y 2 is —C(═O)—NR b — or the like; R a is optionally substituted alkyl, or the like; R b is a hydrogen atom or the like; R 6 is a hydrogen atom or the like; R 7 and R 8 are each independently optionally substituted alkyl or the like; or R 7 and R 8 are taken together with the adjacent carbon atoms to form a 5 to 8 membered ring which may contain a heteroatom(s) and/or an unsaturated bond(s); R 9 is optionally substituted alkyl which may contain a heteroatom(s) and/or an unsaturated bond(s), or the like; X is a oxygen atom or the like.
• US8088924B2
  申请人：——

  公开号：US8088924B2

  公开（公告）日：2012-01-03
• Selective CB2 agonists with anti-pruritic activity: Discovery of potent and orally available bicyclic 2-pyridones
  作者：Ken-ichi Kusakabe、Yasuyoshi Iso、Yukio Tada、Masahiro Sakagami、Yasuhide Morioka、Nobuo Chomei、Satomi Shinonome、Keiko Kawamoto、Hideyuki Takenaka、Kiyoshi Yasui、Hiroshi Hamana、Kohji Hanasaki

  DOI：10.1016/j.bmc.2013.03.030

  日期：2013.6

  The CB2 receptor has emerged as a potential target for the treatment of pruritus as well as pain without CB1-mediated side effects. We previously identified 2-pyridone derivatives 1 and 2 as potent CB2 agonists; however, this series of compounds was found to have unacceptable pharmacokinetic profiles with no significant effect in vivo. To improve these profiles, we performed further structural optimization of 1 and 2, which led to the discovery of bicyclic 2-pyridone 18e with improved CB2 affinity and selectivity over CB1. In a mouse pruritus model, 18e inhibited compound 48/80 induced scratching behavior at a dose of 100 mg/kg. In addition, the docking model of 18e with an active-state CB2 homology model indicated the structural basis of its high affinity and selectivity over CB1. (C) 2013 Published by Elsevier Ltd.