1-butyl-5,6-dimethyl-3-O-(benzoxazol-2-yl)-2-thiopyridone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-butyl-5,6-dimethyl-3-O-(benzoxazol-2-yl)-2-thiopyridone
• 英文别名: 3-(1,3-Benzoxazol-2-yloxy)-1-butyl-5,6-dimethylpyridine-2-thione
• 化学式: C₁₈H₂₀N₂O₂S
• 分子量: 328.435
• InChiKey: LNLLTFBEWQFKPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 3-(N-benzyl-2-methoxyacetamido)-2-methylbut-2-enoate 在 劳森试剂 、 palladium 10% on activated carbon 、 氢气 、 sodium ethanolate 、 吡啶盐酸盐 、 sodium hydride 、 potassium carbonate 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 正丁醇 为溶剂， 200.0 ℃ 、500.01 kPa 条件下， 反应 108.5h， 生成 1-butyl-5,6-dimethyl-3-O-(benzoxazol-2-yl)-2-thiopyridone
  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

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。
• Design, synthesis, and binding mode prediction of 2-pyridone-based selective CB2 receptor agonists
  作者：Ken-ichi Kusakabe、Yukio Tada、Yasuyoshi Iso、Masahiro Sakagami、Yasuhide Morioka、Nobuo Chomei、Satomi Shinonome、Keiko Kawamoto、Hideyuki Takenaka、Kiyoshi Yasui、Hiroshi Hamana、Kohji Hanasaki

  DOI：10.1016/j.bmc.2013.01.006

  日期：2013.4

  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.