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

2-Phenylpyrazolo [1, 5-a] pyrimidin-7-ones. A new class of nonsteroidal antiinflammatory drugs devoid of ulcerogenic activity

G Auzzi, F Bruni, L Cecchi, A Costanzo…

Index: Journal of Medicinal Chemistry, 1983 , vol. 26, # 12 p. 1706 - 1709

Full Text: HTML

Citation Number: 31

Abstract

... Med. Chem., 20, 386 (1977). 0022-262318311826-1706$01.50/0 0 1983 American Chemical Society Page 2. 2-Phenylpyrazolo[l,Sa]pyrimidin- 7-ones Journal of Medicinal Chemistry, 1983, Vol. 26, No, 12 1707 Table ...

Diethyl sulfate Structure

Diethyl sulfate

2-methyl-1H-pyrazolo[1,5-a]pyrimidin-7-one Structure

2-methyl-1H-pyr...

~23%

4-ethyl-2-methylpyrazolo[1,5-a]pyrimidin-7-one Structure

4-ethyl-2-methy...

4-ethyl-4,7-dihydro-2-phenylpyrazolo(1,5-a)pyrimidin-7-one Structure

4-ethyl-4,7-dih...

~6%

3-bromo-4-ethyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

3-bromo-4-ethyl...

3,6-dibromo-4-ethyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

3,6-dibromo-4-e...

4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4,7-dihydro-2-p...

~%

3-bromo-4-ethyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

3-bromo-4-ethyl...

4,7-dihydro-2-phenyl-3-thiocyanatopyrazolo[1,5-a]pyrimidin-7-one Structure

4,7-dihydro-2-p...

~65%

4-ethyl-3-[(4-ethyl-7-oxo-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)disulfanyl]-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4-ethyl-3-[(4-e...

4-ethyl-4,7-dihydro-2-phenylpyrazolo(1,5-a)pyrimidin-7-one Structure

4-ethyl-4,7-dih...

~%

4-ethyl-3-[(4-ethyl-7-oxo-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)disulfanyl]-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4-ethyl-3-[(4-e...

4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4,7-dihydro-2-p...

~%

4-ethyl-3-[(4-ethyl-7-oxo-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)disulfanyl]-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4-ethyl-3-[(4-e...

Ethyl iodide Structure

4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4,7-dihydro-2-p...

~30%

4-ethyl-4,7-dihydro-2-phenylpyrazolo(1,5-a)pyrimidin-7-one Structure

4-ethyl-4,7-dih...

4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4,7-dihydro-2-p...

~24%

3-nitroso-2-phenyl-1H-pyrazolo[1,5-a]pyrimidin-7-one Structure

3-nitroso-2-phe...

Ethyl iodide Structure

3-nitroso-2-phenyl-1H-pyrazolo[1,5-a]pyrimidin-7-one Structure

3-nitroso-2-phe...

~15%

4-ethyl-3-nitroso-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4-ethyl-3-nitro...

4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4,7-dihydro-2-p...

~%

4-ethyl-3-nitroso-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4-ethyl-3-nitro...

Ethyl iodide Structure

2-PHENYL-PYRAZOLO[1,5-A]PYRIMIDIN-5-OL Structure

2-PHENYL-PYRAZO...

~4%

5-ethoxy-2-phenylpyrazolo[1,5-a]pyrimidine Structure

5-ethoxy-2-phen...

4-ethyl-2-phenylpyrazolo[1,5-a]pyrimidin-5-one Structure

4-ethyl-2-pheny...

4-ethyl-4,7-dihydro-2-phenylpyrazolo(1,5-a)pyrimidin-7-one Structure

4-ethyl-4,7-dih...

~5%

3-bromo-4-ethyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

3-bromo-4-ethyl...

3,6-dibromo-4-ethyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

3,6-dibromo-4-e...

4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4,7-dihydro-2-p...

~%

3,6-dibromo-4-ethyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

3,6-dibromo-4-e...

2-Iodopropane Structure

4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4,7-dihydro-2-p...

~22%

2-phenyl-4-propan-2-ylpyrazolo[1,5-a]pyrimidin-7-one Structure

2-phenyl-4-prop...

Butyl iodide Structure

4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4,7-dihydro-2-p...

~30%

4-butyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4-butyl-2-pheny...

1-Iodopropane Structure

2-PHENYL-PYRAZOLO[1,5-A]PYRIMIDIN-5-OL Structure

2-PHENYL-PYRAZO...

~6%

2-phenyl-5-propoxypyrazolo[1,5-a]pyrimidine Structure

2-phenyl-5-prop...

2-phenyl-4-propylpyrazolo[1,5-a]pyrimidin-5-one Structure

2-phenyl-4-prop...

Ethyl iodide Structure

2-PHENYL-PYRAZOLO[1,5-A]PYRIMIDIN-5-OL Structure

2-PHENYL-PYRAZO...

~5%

5-ethoxy-2-phenylpyrazolo[1,5-a]pyrimidine Structure

5-ethoxy-2-phen...

4-ethyl-2-phenylpyrazolo[1,5-a]pyrimidin-5-one Structure

4-ethyl-2-pheny...

Benzyl chloride Structure

Benzyl chloride

4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4,7-dihydro-2-p...

~39%

4-benzyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4-benzyl-2-phen...

4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4,7-dihydro-2-p...

2-Chlor-1,1-diethoxyethan Structure

2-Chlor-1,1-die...

~23%

4-(2,2-diethoxyethyl)-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4-(2,2-diethoxy...

4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4,7-dihydro-2-p...

2-Chloroethanol Structure

2-Chloroethanol

~18%

4-(2-hydroxyethyl)-2-phenylpyrazolo[1,5-a]pyrimidin-7-one Structure

4-(2-hydroxyeth...

1-Iodopropane Structure

2-PHENYL-PYRAZOLO[1,5-A]PYRIMIDIN-5-OL Structure

2-PHENYL-PYRAZO...

~7%

2-phenyl-5-propoxypyrazolo[1,5-a]pyrimidine Structure

2-phenyl-5-prop...

2-phenyl-4-propylpyrazolo[1,5-a]pyrimidin-5-one Structure

2-phenyl-4-prop...

Diethyl sulfate Structure

Diethyl sulfate

2-(4-methylphenyl)-1H-pyrazolo[1,5-a]pyrimidin-7-one Structure

2-(4-methylphen...

~34%

4-ethyl-2-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-7-one Structure

4-ethyl-2-(4-me...