e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis and biological evaluation of 2-alkoxyphenyl-6-(substituted phenyl)-1, 3, 4-thiadiazole-[3, 2-a]-s-triazin-5, 7-diones and 1-(alkyl and substituted phenyl)-3-[5- …

…, R Pignatello, A Panico, G Mazzone, A Corsaro…

Index: Puglisi, Giovanni; Pignatello, Rosario; Panico, Annamaria; Mazzone, Gioacchino; Corsaro, Antonio; et al. European Journal of Medicinal Chemistry, 1989 , vol. 24, p. 277 - 286

Full Text: HTML

Citation Number: 7

Abstract

Abstract As an extension of a previous work, in which a series of 2-alkoxyphenyl-6-phenyl-1, 3, 4-thiadiazole-[3, 2-a]-s-triazin-5, 7-diones were synthesized and found to possess analgesic activity, a new series of analogues substituted in the 6-phenyl ring has been prepared and tested with the aim of examining the variations induced by phenyl substituents in biological activity, and thus obtaining useful information about the structure—activity ...

5-(3,4,5-Trimethoxyphenyl)-1,3,4-thiadiazol-2-amine Structure

5-(3,4,5-Trimet...

p-Chlorophenyl isocyanate Structure

p-Chlorophenyl ...

~77%

6-(4-chlorophenyl)-2-(3,4,5-trimethoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

6-(4-chlorophen...

5-(3,4,5-Trimethoxyphenyl)-1,3,4-thiadiazol-2-amine Structure

5-(3,4,5-Trimet...

~%

6-(4-chlorophenyl)-2-(3,4,5-trimethoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

6-(4-chlorophen...

p-Chlorophenyl isocyanate Structure

p-Chlorophenyl ...

~%

6-(4-chlorophenyl)-2-(3,4,5-trimethoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

6-(4-chlorophen...

p-Chlorophenyl isocyanate Structure

p-Chlorophenyl ...

1-(4-chlorophenyl)-3-(5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-yl)urea Structure

1-(4-chlorophen...

~%

6-(4-chlorophenyl)-2-(3,4,5-trimethoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

6-(4-chlorophen...

4-Fluorophenylisocyanate Structure

4-Fluorophenyli...

5-(4-ethoxy-3,5-dimethoxyphenyl)-1,3,4-Thiadiazol-2-amine Structure

5-(4-ethoxy-3,5...

~72%

2-(4-ethoxy-3,5-dimethoxyphenyl)-6-(4-fluorophenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(4-ethoxy-3,5...

4-Fluorophenylisocyanate Structure

4-Fluorophenyli...

~%

2-(4-ethoxy-3,5-dimethoxyphenyl)-6-(4-fluorophenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(4-ethoxy-3,5...

5-(4-ethoxy-3,5-dimethoxyphenyl)-1,3,4-Thiadiazol-2-amine Structure

5-(4-ethoxy-3,5...

~%

2-(4-ethoxy-3,5-dimethoxyphenyl)-6-(4-fluorophenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(4-ethoxy-3,5...

4-Fluorophenylisocyanate Structure

4-Fluorophenyli...

1-(5-(4-ethoxy-3,5-dimethoxyphenyl)-1,3,4-thiadiazol-2-yl)-3-(4-fluorophenyl)urea Structure

1-(5-(4-ethoxy-...

~%

2-(4-ethoxy-3,5-dimethoxyphenyl)-6-(4-fluorophenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(4-ethoxy-3,5...

5-(2H-1,3-benzodioxol-5-yl)-1,3,4-thiadiazol-2-amine Structure

5-(2H-1,3-benzo...

4-Fluorophenylisocyanate Structure

4-Fluorophenyli...

~71%

2-(1,3-benzodioxol-5-yl)-6-(4-fluorophenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(1,3-benzodio...

5-(2H-1,3-benzodioxol-5-yl)-1,3,4-thiadiazol-2-amine Structure

5-(2H-1,3-benzo...

~%

2-(1,3-benzodioxol-5-yl)-6-(4-fluorophenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(1,3-benzodio...

4-Fluorophenylisocyanate Structure

4-Fluorophenyli...

~%

2-(1,3-benzodioxol-5-yl)-6-(4-fluorophenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(1,3-benzodio...

4-Fluorophenylisocyanate Structure

4-Fluorophenyli...

N/A Structure

~%

2-(1,3-benzodioxol-5-yl)-6-(4-fluorophenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(1,3-benzodio...

5-(2H-1,3-benzodioxol-5-yl)-1,3,4-thiadiazol-2-amine Structure

5-(2H-1,3-benzo...

p-Tolyl Isocyanate Structure

p-Tolyl Isocyanate

~70%

2-(1,3-benzodioxol-5-yl)-6-(4-methylphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(1,3-benzodio...

p-Tolyl Isocyanate Structure

p-Tolyl Isocyanate

N/A Structure

~%

2-(1,3-benzodioxol-5-yl)-6-(4-methylphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(1,3-benzodio...

5-(2H-1,3-benzodioxol-5-yl)-1,3,4-thiadiazol-2-amine Structure

5-(2H-1,3-benzo...

~%

2-(1,3-benzodioxol-5-yl)-6-(4-methylphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(1,3-benzodio...

p-Tolyl Isocyanate Structure

p-Tolyl Isocyanate

~%

2-(1,3-benzodioxol-5-yl)-6-(4-methylphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(1,3-benzodio...

5-(2H-1,3-benzodioxol-5-yl)-1,3,4-thiadiazol-2-amine Structure

5-(2H-1,3-benzo...

4-Methoxyphenylisocyanate Structure

4-Methoxyphenyl...

~74%

2-(1,3-benzodioxol-5-yl)-6-(4-methoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(1,3-benzodio...

4-Methoxyphenylisocyanate Structure

4-Methoxyphenyl...

1-(5-(benzo[d][1,3]dioxol-5-yl)-1,3,4-thiadiazol-2-yl)-3-(4-methoxyphenyl)urea Structure

1-(5-(benzo[d][...

~%

2-(1,3-benzodioxol-5-yl)-6-(4-methoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(1,3-benzodio...

5-(2H-1,3-benzodioxol-5-yl)-1,3,4-thiadiazol-2-amine Structure

5-(2H-1,3-benzo...

~%

2-(1,3-benzodioxol-5-yl)-6-(4-methoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(1,3-benzodio...

4-Methoxyphenylisocyanate Structure

4-Methoxyphenyl...

~%

2-(1,3-benzodioxol-5-yl)-6-(4-methoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(1,3-benzodio...

5-(3,4,5-Trimethoxyphenyl)-1,3,4-thiadiazol-2-amine Structure

5-(3,4,5-Trimet...

4-nitrophenyl isocyanate Structure

4-nitrophenyl i...

~61%

6-(4-nitrophenyl)-2-(3,4,5-trimethoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

6-(4-nitropheny...

5-(3,4,5-Trimethoxyphenyl)-1,3,4-thiadiazol-2-amine Structure

5-(3,4,5-Trimet...

~%

6-(4-nitrophenyl)-2-(3,4,5-trimethoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

6-(4-nitropheny...

4-nitrophenyl isocyanate Structure

4-nitrophenyl i...

~%

6-(4-nitrophenyl)-2-(3,4,5-trimethoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

6-(4-nitropheny...

4-nitrophenyl isocyanate Structure

4-nitrophenyl i...

N/A Structure

~%

6-(4-nitrophenyl)-2-(3,4,5-trimethoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

6-(4-nitropheny...

5-(3,4,5-Trimethoxyphenyl)-1,3,4-thiadiazol-2-amine Structure

5-(3,4,5-Trimet...

p-Tolyl Isocyanate Structure

p-Tolyl Isocyanate

~77%

6-(4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

6-(4-methylphen...

p-Tolyl Isocyanate Structure

p-Tolyl Isocyanate

N/A Structure

~%

6-(4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

6-(4-methylphen...

5-(3,4,5-Trimethoxyphenyl)-1,3,4-thiadiazol-2-amine Structure

5-(3,4,5-Trimet...

~%

6-(4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

6-(4-methylphen...

p-Tolyl Isocyanate Structure

p-Tolyl Isocyanate

~%

6-(4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

6-(4-methylphen...

4-Methoxyphenylisocyanate Structure

4-Methoxyphenyl...

5-(4-ethoxy-3,5-dimethoxyphenyl)-1,3,4-Thiadiazol-2-amine Structure

5-(4-ethoxy-3,5...

~67%

2-(4-ethoxy-3,5-dimethoxyphenyl)-6-(4-methoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(4-ethoxy-3,5...

4-Methoxyphenylisocyanate Structure

4-Methoxyphenyl...

1-(5-(4-ethoxy-3,5-dimethoxyphenyl)-1,3,4-thiadiazol-2-yl)-3-(4-methoxyphenyl)urea Structure

1-(5-(4-ethoxy-...

~%

2-(4-ethoxy-3,5-dimethoxyphenyl)-6-(4-methoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(4-ethoxy-3,5...

4-Methoxyphenylisocyanate Structure

4-Methoxyphenyl...

~%

2-(4-ethoxy-3,5-dimethoxyphenyl)-6-(4-methoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(4-ethoxy-3,5...

5-(4-ethoxy-3,5-dimethoxyphenyl)-1,3,4-Thiadiazol-2-amine Structure

5-(4-ethoxy-3,5...

~%

2-(4-ethoxy-3,5-dimethoxyphenyl)-6-(4-methoxyphenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione Structure

2-(4-ethoxy-3,5...