N'-(5-aminobenzo[d]thiazol-2-yl)-N,N-dimethylformimidamide | 1372423-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: N'-(5-aminobenzo[d]thiazol-2-yl)-N,N-dimethylformimidamide
• 英文别名: N'-(5-amino-1,3-benzothiazol-2-yl)-N,N-dimethylmethanimidamide
• CAS: 1372423-24-9
• 化学式: C₁₀H₁₂N₄S
• 分子量: 220.298
• InChiKey: VRYLGYIZMQBYKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-萘磺酰氯 、 N'-(5-aminobenzo[d]thiazol-2-yl)-N,N-dimethylformimidamide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 以14%的产率得到N,N-dimethyl-N'-(6-(naphthalene-1-sulfonamido)benzo-[d]thiazol-2-yl)formimidamide
  参考文献：
  名称：

  Synthesis and biological evaluation of benzoisothiazole derivatives possessing N,N-dimethylformimidamide group as 5-HT6 receptor antagonists

  摘要：

  A series of novel N,N-dimethyl-N'-(5-(Ar-sulfonamido) benzo[d]isothiazol-3-yl)formimidamides was designed and synthesized as 5-HT6 ligands. Here N,N-dimethyl formimidamides was used as a replacement for an aminoethyl moiety. In vitro functional assays demonstrated compounds 9b and 9i significantly inhibited the 5-HT-induced Ca2+ increases (9b; IC50 = 0.36 mu M and 9i; IC50 = 0.44 mu M), indicating that 9b and 9i were potent 5-HT6 receptor antagonists. Compounds 9i also showed good selectivity on the 5-HT6 over 5-HT4 and 5-HT7 receptors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.020
• 作为产物：
  描述：

  N,N-dimethyl-N'-(5-nitrobenzo[d]thiazol-2-yl)formimidamide 在 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以31%的产率得到N'-(5-aminobenzo[d]thiazol-2-yl)-N,N-dimethylformimidamide
  参考文献：
  名称：

  Synthesis and biological evaluation of benzoisothiazole derivatives possessing N,N-dimethylformimidamide group as 5-HT6 receptor antagonists

  摘要：

  A series of novel N,N-dimethyl-N'-(5-(Ar-sulfonamido) benzo[d]isothiazol-3-yl)formimidamides was designed and synthesized as 5-HT6 ligands. Here N,N-dimethyl formimidamides was used as a replacement for an aminoethyl moiety. In vitro functional assays demonstrated compounds 9b and 9i significantly inhibited the 5-HT-induced Ca2+ increases (9b; IC50 = 0.36 mu M and 9i; IC50 = 0.44 mu M), indicating that 9b and 9i were potent 5-HT6 receptor antagonists. Compounds 9i also showed good selectivity on the 5-HT6 over 5-HT4 and 5-HT7 receptors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.020