2,5,6,8-tetrahydro-3H-imidazo[2,1-c][1,4]thiazine | 60928-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻嗪类
• 英文名称: 2,5,6,8-tetrahydro-3H-imidazo[2,1-c][1,4]thiazine
• 英文别名: 2,3,5,6-tetrahydro-8H-imidazo[2,1-c] [1,4]-thiazine；2,5,6,8-tetrahydro-3H-imidazo[2,1-c][1,4]thiazine；3,5,6,8-tetrahydro-2H-imidazo[2,1-c][1,4]thiazine
• CAS: 60928-26-9
• 化学式: C₆H₁₀N₂S
• 分子量: 142.225
• InChiKey: XUEIDXFRSONAIS-UHFFFAOYSA-N

物化性质

• 沸点：
  304.7±35.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5,6,8-tetrahydro-3H-imidazo[2,1-c][1,4]thiazine 在 sodium periodate 作用下， 以 甲醇 为溶剂， 生成 2,5,6,8-tetrahydro-3H-imidazo[2,1-c][1,4]thiazine 7-oxide
  参考文献：
  名称：

  Cyclic amidine inhibitors of indolamine N-methyltransferase

  摘要：

  Syntheses of a large number of mono- and bicyclic, as well as a few tricyclic, amidine derivatives related to 2,3,4,6,7,8,-hexahydropyrrolo[1,2-a]pyrimidine (DBN) are reported. In vitro potencies for inhibition of the enzyme indolamine N-methyltransferase (INMT) from rabbit and human lung are presented. Four bicyclic amidine derivatives and 11 monocyclic derivatives were found to be equal or superior to DBN in in vitro potencies. With the bicyclic amidines, increasing ring size or introduction of substituents reduced activity. Among the monocyclic analogues, the most potent representatives were five- or six-membered systems with an exocyclic imino group, combined with methyl of ethyl substituents on the endocyclic nitrogen. Introduction of additonal substituents decreased inhibitory potency. 2,3,5,6-Tetrahydro-8H-imidazo[2,1-c][1,4]thiazine and 3-methyl-2-iminothiazolidine have been shown to cause inhibition of lung INMT when administered orally to rabbits.

  DOI：

  10.1021/jm00189a004
• 作为产物：
  描述：

  硫代吗啉酮 、 2-溴乙胺氢溴酸盐 生成 2,5,6,8-tetrahydro-3H-imidazo[2,1-c][1,4]thiazine
  参考文献：
  名称：

  Cyclic amidine inhibitors of indolamine N-methyltransferase

  摘要：

  Syntheses of a large number of mono- and bicyclic, as well as a few tricyclic, amidine derivatives related to 2,3,4,6,7,8,-hexahydropyrrolo[1,2-a]pyrimidine (DBN) are reported. In vitro potencies for inhibition of the enzyme indolamine N-methyltransferase (INMT) from rabbit and human lung are presented. Four bicyclic amidine derivatives and 11 monocyclic derivatives were found to be equal or superior to DBN in in vitro potencies. With the bicyclic amidines, increasing ring size or introduction of substituents reduced activity. Among the monocyclic analogues, the most potent representatives were five- or six-membered systems with an exocyclic imino group, combined with methyl of ethyl substituents on the endocyclic nitrogen. Introduction of additonal substituents decreased inhibitory potency. 2,3,5,6-Tetrahydro-8H-imidazo[2,1-c][1,4]thiazine and 3-methyl-2-iminothiazolidine have been shown to cause inhibition of lung INMT when administered orally to rabbits.

  DOI：

  10.1021/jm00189a004

文献信息

• Imidazothiazines, derivatives and analogues thereof
  申请人：Merck & Co., Inc.

  公开号：US03973017A1

  公开（公告）日：1976-08-03

  Disclosed are 2,3,5,6-tetrahydro-8H-imidazo-[2,1-c][1,4]thiazines, analogues and derivatives thereof which are effective in inhibiting indoleamine-N-methyl transferase and thus useful in the treatment of mental aberrations, such as schizophrenia. Also disclosed are processes for the preparation of such imidazothiazines; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions.

  本发明公开了2,3,5,6-四氢-8H-咪唑[2,1-c][1,4]噻嗪、类似物和衍生物，其有效抑制吲哚胺-N-甲基转移酶，因此在治疗精神错乱，如精神分裂症方面有用。本发明还公开了制备此类咪唑噻嗪的方法；包含此类化合物的制药组合物；以及包括给予此类化合物和组合物的治疗方法。
• US3973017A
  申请人：——

  公开号：US3973017A

  公开（公告）日：1976-08-03
• US4025625A
  申请人：——

  公开号：US4025625A

  公开（公告）日：1977-05-24