N-(6-fluorobenzo[d]thiazol-2-yl)-6-methylbenzo[d]thiazol-2-amine | 1355679-00-3

• 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-(6-fluorobenzo[d]thiazol-2-yl)-6-methylbenzo[d]thiazol-2-amine
• 英文别名: N-(6-fluoro-1,3-benzothiazol-2-yl)-6-methyl-1,3-benzothiazol-2-amine
• CAS: 1355679-00-3
• 化学式: C₁₅H₁₀FN₃S₂
• 分子量: 315.395
• InChiKey: ICGLFOUONOZMEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  94.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(p-fluorophenyl)-3-(6-methylbenzo[d]thiazol-2-yl)thiourea 在 1,3-di-n-butyl-1H-imidazol-3-ium tribromide 作用下， 反应 0.58h， 以87%的产率得到N-(6-fluorobenzo[d]thiazol-2-yl)-6-methylbenzo[d]thiazol-2-amine
  参考文献：
  名称：

  1,3-二正丁基咪唑鎓三溴化物介导的苯并噻唑基氨基甲酸酯的化学选择性氧化环化：合成N-双-双-苯并噻唑衍生物的新方法

  摘要：

  发现4-（N，N-二甲基氨基）吡啶是使用2-氨基苯并噻唑和苯基异硫氰酸酯合成苯并噻唑基氨基甲酸酯衍生物的有效催化剂，在离子液体[bbim] [Br 3 ]于70°C处理后，独家提供形成的ñ -双-苯并噻唑以良好的收率衍生物。J.杂环化​​学。（2012）。

  DOI：

  10.1002/jhet.736

文献信息

• 1,3-Di-n-butylimidazolium tribromide-mediated chemoselective oxidative cyclization of benzothiazoyl carbaimides: A novel approach toward the synthesis of N-bis-benzothiazole derivatives
  作者：Ravindra M. Kumbhare、Tulshiram Dadmal、Umesh Kosurkar、K. Vijay Kumar

  DOI：10.1002/jhet.736

  日期：2012.3

  4‐(N,N‐Dimethylamino)pyridine is found to be an efficient catalyst for the synthesis of benzothiazoyl carbaimide derivatives using 2‐aminobenzothiazoles and phenylisothiocyanates, which on treatment with ionic liquid [bbim][Br3] at 70°C afforded exclusive formation of N‐bis‐benzothiazole derivatives in good yield. J. Heterocyclic Chem., (2012).

  发现4-（N，N-二甲基氨基）吡啶是使用2-氨基苯并噻唑和苯基异硫氰酸酯合成苯并噻唑基氨基甲酸酯衍生物的有效催化剂，在离子液体[bbim] [Br 3 ]于70°C处理后，独家提供形成的ñ -双-苯并噻唑以良好的收率衍生物。J.杂环化​​学。（2012）。
• Synthesis and cytotoxic evaluation of thiourea and N-bis-benzothiazole derivatives: A novel class of cytotoxic agents
  作者：Ravindra M. Kumbhare、Tulshiram Dadmal、Umesh Kosurkar、V. Sridhar、J. Venkateswara Rao

  DOI：10.1016/j.bmcl.2011.10.106

  日期：2012.1

  Benzothiazolyl thiocarbamides has been achieved using a catalytic amount of 4-dimethylaminopyridine (DMAP) followed by its chemoselective oxidative cyclization with 1,3-di-n-butylimidazolium tribromide[bbim][Br-3] to afford the N-bis-benzothiazole derivatives. All the synthesized compounds were evaluated for cytotoxic activity against two human monocytic cell lines (U 937, THP-1) and a mouse melanoma cell line (B16-F10). Based on their IC50 values, the majority of the benzothiazolyl thiocarbamides and N-bis-benzothiazoles had significant antiproliferative activity on U 937 and B16-F10 cells, the compounds 3b, 3e, 3f, 3k, 6c and 6h were found to be the most active. The present findings indicate clearly that the compound 3e exhibited more antiproliferative activity on U 937 cells than the standard molecule, etoposide. Nevertheless, these compounds have shown comparatively less cytotoxicity towards THP-1 cells. (C) 2011 Elsevier Ltd. All rights reserved.