3-hydroxy-5,6-dimethyl-1-pentylpyridine-2(1H)-thione | 1428733-18-9

• 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: 3-hydroxy-5,6-dimethyl-1-pentylpyridine-2(1H)-thione
• 英文别名: 3-Hydroxy-5,6-dimethyl-1-pentylpyridine-2-thione
• CAS: 1428733-18-9
• 化学式: C₁₂H₁₉NOS
• 分子量: 225.355
• InChiKey: ZCBSYVGMVPYZSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯苯并恶唑 、 3-hydroxy-5,6-dimethyl-1-pentylpyridine-2(1H)-thione 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以64%的产率得到3-(1,3-Benzoxazol-2-yloxy)-5,6-dimethyl-1-pentylpyridine-2-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：

  ethyl 3-(benzylamino)-2-methylbut-2-enoate 在 劳森试剂 、 吡啶 、 palladium 10% on activated carbon 、 氢气 、 sodium ethanolate 、 吡啶盐酸盐 、 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 、 正丁醇 为溶剂， 5.0~200.0 ℃ 、500.01 kPa 条件下， 反应 109.5h， 生成 3-hydroxy-5,6-dimethyl-1-pentylpyridine-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