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

Synthesis and pharmacological properties of pyrazolotriazolopyrimidine derivatives

…, S Guccione, G Romeo, L Monsu'Scolaro…

Index: Russo, F; Guccione, S; Romeo, G; Monsu'Scolaro, L; Pucci, S; et al. European Journal of Medicinal Chemistry, 1992 , vol. 27, # 1 p. 73 - 80

Full Text: HTML

Citation Number: 31

Abstract

Abstract As a part of research on anti-inflammatory-analgesic compounds, pyrazolotriazolopyrimidines were prepared by cycling the corresponding 2-phenylamino-3- aminopyrazolo [3, 4-d] pyrimidin-4-one derivatives 3a–h with triethylorthoformate, in the presence of p-toluenesulfonic acid. The results of the pharmacological screening indicate that some of the derivatives which were tested, especially 3c and 6e, showed a good anti- ...

ethyl 5-(3-(4-bromophenyl)thioureido)-1H-pyrazole-4-carboxylate Structure

ethyl 5-(3-(4-b...

~%

8-(4-bromophenyl)-1H,4H,8H-pyrazolo<3,4-d><1,2,4>triazolo<1,5-a>pyrimidin-4-one Structure

8-(4-bromopheny...

4-bromophenyl isothiocyanate Structure

4-bromophenyl i...

~%

8-(4-bromophenyl)-1H,4H,8H-pyrazolo<3,4-d><1,2,4>triazolo<1,5-a>pyrimidin-4-one Structure

8-(4-bromopheny...

5-amino-6-(4-bromoanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(4-br...

Triethyl orthoformate Structure

Triethyl orthof...

~40%

8-(4-bromophenyl)-1H,4H,8H-pyrazolo<3,4-d><1,2,4>triazolo<1,5-a>pyrimidin-4-one Structure

8-(4-bromopheny...

ethyl 3-(3-(4-methoxyphenyl)thioureido)-1H-pyrazole-4-carboxylate Structure

ethyl 3-(3-(4-m...

~70%

5-amino-6-(4-methoxyanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(4-me...

4-methoxyphenylisothiocyanate Structure

4-methoxyphenyl...

~%

5-amino-6-(4-methoxyanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(4-me...

5-amino-6-anilino-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-anili...

~60%

5-amino-6-anilino-1H-pyrazolo[3,4-d]pyrimidine-4-thione Structure

5-amino-6-anili...

Phenyl isothiocyanate Structure

Phenyl isothioc...

~%

5-amino-6-anilino-1H-pyrazolo[3,4-d]pyrimidine-4-thione Structure

5-amino-6-anili...

ethyl 3-(3-phenylthioureido)-1H-pyrazole-4-carboxylate Structure

ethyl 3-(3-phen...

~%

5-amino-6-anilino-1H-pyrazolo[3,4-d]pyrimidine-4-thione Structure

5-amino-6-anili...

ethyl 5-(3-(4-chlorophenyl)thioureido)-1H-pyrazole-4-carboxylate Structure

ethyl 5-(3-(4-c...

~53%

5-amino-6-(4-chloroanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(4-ch...

4-chlorophenyl isothiocyanate Structure

4-chlorophenyl ...

~%

5-amino-6-(4-chloroanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(4-ch...

5-amino-6-(4-chloroanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(4-ch...

Triethyl orthoformate Structure

Triethyl orthof...

~48%

brn 4880077 Structure

4-chlorophenyl isothiocyanate Structure

4-chlorophenyl ...

~%

brn 4880077 Structure

ethyl 5-(3-(4-chlorophenyl)thioureido)-1H-pyrazole-4-carboxylate Structure

ethyl 5-(3-(4-c...

~%

brn 4880077 Structure

5-amino-6-(4-fluoroanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(4-fl...

Triethyl orthoformate Structure

Triethyl orthof...

~65%

brn 4880030 Structure

ethyl 5-(3-(4-fluorophenyl)thioureido)-1H-pyrazole-4-carboxylate Structure

ethyl 5-(3-(4-f...

~%

brn 4880030 Structure

4-Fluorophenyl isothiocyanate Structure

4-Fluorophenyl ...

~%

brn 4880030 Structure

ethyl 5-(3-(4-bromophenyl)thioureido)-1H-pyrazole-4-carboxylate Structure

ethyl 5-(3-(4-b...

~45%

5-amino-6-(4-bromoanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(4-br...

4-bromophenyl isothiocyanate Structure

4-bromophenyl i...

~%

5-amino-6-(4-bromoanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(4-br...

ethyl 5-(3-(4-fluorophenyl)thioureido)-1H-pyrazole-4-carboxylate Structure

ethyl 5-(3-(4-f...

~48%

5-amino-6-(4-fluoroanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(4-fl...

4-Fluorophenyl isothiocyanate Structure

4-Fluorophenyl ...

~%

5-amino-6-(4-fluoroanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(4-fl...

5-amino-6-(4-methylanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(4-me...

Triethyl orthoformate Structure

Triethyl orthof...

~45%

brn 4878225 Structure

ethyl 5-(3-(p-tolyl)thioureido)-1H-pyrazole-4-carboxylate Structure

ethyl 5-(3-(p-t...

~%

brn 4878225 Structure

4-Methylphenyl isothiocyanate Structure

4-Methylphenyl ...

~%

brn 4878225 Structure

2-chlorophenyl isothiocyanate Structure

2-chlorophenyl ...

~%

brn 4880598 Structure

N/A Structure

~%

brn 4880598 Structure

5-amino-6-(2-chloroanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(2-ch...

Triethyl orthoformate Structure

Triethyl orthof...

~29%

brn 4880598 Structure

ethyl 5-(3-(p-tolyl)thioureido)-1H-pyrazole-4-carboxylate Structure

ethyl 5-(3-(p-t...

~58%

5-amino-6-(4-methylanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(4-me...

4-Methylphenyl isothiocyanate Structure

4-Methylphenyl ...

~%

5-amino-6-(4-methylanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(4-me...

5-amino-6-(4-chloroanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(4-ch...

~50%

5-amino-6-(4-chloroanilino)-1H-pyrazolo[3,4-d]pyrimidine-4-thione Structure

5-amino-6-(4-ch...

4-chlorophenyl isothiocyanate Structure

4-chlorophenyl ...

~%

5-amino-6-(4-chloroanilino)-1H-pyrazolo[3,4-d]pyrimidine-4-thione Structure

5-amino-6-(4-ch...

ethyl 5-(3-(4-chlorophenyl)thioureido)-1H-pyrazole-4-carboxylate Structure

ethyl 5-(3-(4-c...

~%

5-amino-6-(4-chloroanilino)-1H-pyrazolo[3,4-d]pyrimidine-4-thione Structure

5-amino-6-(4-ch...

N/A Structure

~87%

5-amino-6-(2-chloroanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(2-ch...

2-chlorophenyl isothiocyanate Structure

2-chlorophenyl ...

~%

5-amino-6-(2-chloroanilino)-1H-pyrazolo[3,4-d]pyrimidin-4-one Structure

5-amino-6-(2-ch...