2-(1-naphthyl)imino-5,5-pentamethylene-5,6-dihydro-4H-1,3-thiazine | 848406-37-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-naphthyl)imino-5,5-pentamethylene-5,6-dihydro-4H-1,3-thiazine
• 英文别名: 2-(1-naphthyl)-5,5-pentamethylene-1,3-thiazine；N-naphthalen-1-yl-2-thia-4-azaspiro[5.5]undec-3-en-3-amine
• CAS: 848406-37-1
• 化学式: C₁₉H₂₂N₂S
• 分子量: 310.463
• InChiKey: KYZHCKFPMXNZBQ-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  489.5±28.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-naphthyl)imino-5,5-pentamethylene-5,6-dihydro-4H-1,3-thiazine 、 氯硫醇甲酸甲酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以65%的产率得到S-methyl 3-(naphthalen-1-ylimino)-2-thia-4-azaspiro[5.5]undecane-4-carbothioate
  参考文献：
  名称：

  2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 3: Synthesis and activity of isosteric analogs

  摘要：

  Structure-activity relationships and efforts to optimize the pharmacokinetic pro. le of isosteric analogs of 2-arylimino-5,6-dihydro-4H-1,3-thiazines as cannabinoid receptor agonists are described. Among those examined, compound 25 showed potent affinity for cannabinoid receptor 1 (CB1) and receptor 2 (CB2). This compound displayed oral bioavailability and analgesic activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.070
• 作为产物：
  描述：

  1-萘异硫氰酸酯 在 盐酸 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-(1-naphthyl)imino-5,5-pentamethylene-5,6-dihydro-4H-1,3-thiazine
  参考文献：
  名称：

  2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 2: Orally bioavailable compounds

  摘要：

  Structure-activity; relationships and efforts to optimize the pharmacokinetic profile of a class of 2-arylimino-5,6-dihydro4H-1,3-thiazines as cannabinoid receptor agonists are described. Among the compounds examined, compound 14 showed potent affinity and high selectivity for CB2, and compound 23 showed potent affinities against CB1 and CB2. These compounds displayed oral bioavailability. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.099

文献信息

• EP1659117
  申请人：——

  公开号：——

  公开（公告）日：——
• US7482339B2
  申请人：——

  公开号：US7482339B2

  公开（公告）日：2009-01-27
• 2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 2: Orally bioavailable compounds
  作者：Hiroyuki Kai、Yasuhide Morioka、Minoru Tomida、Tadashi Takahashi、Maki Hattori、Kohji Hanasaki、Katsumi Koike、Hiroki Chiba、Shunji Shinohara、Toshiyuki Kanemasa、Yuka Iwamoto、Kohji Takahashi、Yoshitaka Yamaguchi、Takahiko Baba、Takayoshi Yoshikawa、Hideyuki Takenaka

  DOI：10.1016/j.bmcl.2007.04.099

  日期：2007.7

  Structure-activity; relationships and efforts to optimize the pharmacokinetic profile of a class of 2-arylimino-5,6-dihydro4H-1,3-thiazines as cannabinoid receptor agonists are described. Among the compounds examined, compound 14 showed potent affinity and high selectivity for CB2, and compound 23 showed potent affinities against CB1 and CB2. These compounds displayed oral bioavailability. (C) 2007 Elsevier Ltd. All rights reserved.
• 2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 3: Synthesis and activity of isosteric analogs
  作者：Hiroyuki Kai、Yasuhide Morioka、Yuji Koriyama、Kazuya Okamoto、Yasushi Hasegawa、Maki Hattori、Katsumi Koike、Hiroki Chiba、Shunji Shinohara、Yuka Iwamoto、Kohji Takahashi、Norihiko Tanimoto

  DOI：10.1016/j.bmcl.2008.10.070

  日期：2008.12

  Structure-activity relationships and efforts to optimize the pharmacokinetic pro. le of isosteric analogs of 2-arylimino-5,6-dihydro-4H-1,3-thiazines as cannabinoid receptor agonists are described. Among those examined, compound 25 showed potent affinity for cannabinoid receptor 1 (CB1) and receptor 2 (CB2). This compound displayed oral bioavailability and analgesic activity. (C) 2008 Elsevier Ltd. All rights reserved.