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

Antihypertensive 5, 6-diarylpyridazin-3-ones

R Buchman, JA Scozzie, ZS Ariyan…

Index: Buchman; Scozzie; Ariyan; Heilman; Rippin; Pyne; Powers; Matthews Journal of Medicinal Chemistry, 1980 , vol. 23, # 12 p. 1398 - 1405

Full Text: HTML

Citation Number: 16

Abstract

The synthesis of a series of 5, 6-diarylpyridazinones is described, Some members of this series display an antihypertensive effect in both the spontaneously hypertensive rat (SHR) model and the deoxycorticosteroid@ OCA) model of hypertension. The most potent compounds in the series have halogen substituents on the 5, 6-diphenyl rings, a 0- substituted alkyl group at the 2 position of the ring, and an acetyl or cyano substituent at ...

2-[2'-(isopropylideneamino)ethyl]-4-acetyl-5,6-bis(p-chlorophenyl)-2H-pyridazin-3-one Structure

2-[2'-(isopropy...

~32%

4-acetyl-5,6-bis(4-chlorophenyl)-2-[2-(propan-2-ylamino)ethyl]pyridazin-3-one Structure

4-acetyl-5,6-bi...

4-acetyl-5,6-bis(4-chlorophenyl)-2-(2-aminoethyl)-2H-pyridazin-3-one Structure

4-acetyl-5,6-bi...

~%

4-acetyl-5,6-bis(4-chlorophenyl)-2-[2-(propan-2-ylamino)ethyl]pyridazin-3-one Structure

4-acetyl-5,6-bi...

Ethylene carbonate Structure

Ethylene carbonate

3,4-bis(4-fluorophenyl)-6-oxo-1H-pyridazine-5-carbonitrile Structure

3,4-bis(4-fluor...

~62%

4-Pyridazinecarbonitrile, 5,6-bis(4-fluorophenyl)-2,3-dihydro-2-(2-hydroxyethyl)-3-oxo- Structure

4-Pyridazinecar...

4-Acetyl-5,6-bis(p-chlorophenyl)-2H-pyridazin-3-one Structure

4-Acetyl-5,6-bi...

~52%

4-acetyl-5,6-bis(4-chlorophenyl)-2-(1-hydroxypropan-2-yl)pyridazin-3-one Structure

4-acetyl-5,6-bi...

(E)-1,2-bis(3,4-dichlorophenyl)-2-hydrazonoethan-1-one Structure

(E)-1,2-bis(3,4...

~37%

4-Pyridazinecarbonitrile, 5,6-bis(3,4-dichlorophenyl)-2,3-dihydro-3-ox o- Structure

4-Pyridazinecar...

(E)-1,2-bis(4-bromophenyl)-2-hydrazonoethan-1-one Structure

(E)-1,2-bis(4-b...

~47%

3,4-bis(4-bromophenyl)-6-oxo-1H-pyridazine-5-carbonitrile Structure

3,4-bis(4-bromo...

4-Acetyl-5,6-bis(p-chlorophenyl)-2H-pyridazin-3-one Structure

4-Acetyl-5,6-bi...

~%

4-acetyl-2-(2-aminoethyl)-5,6-bis(4-chlorophenyl)pyridazin-3-one Structure

4-acetyl-2-(2-a...

2-(2-(5-acetyl-3,4-bis(4-chlorophenyl)-6-oxopyridazin-1(6H)-yl)ethyl)isoindoline-1,3-dione Structure

2-(2-(5-acetyl-...

~29%

4-acetyl-2-(2-aminoethyl)-5,6-bis(4-chlorophenyl)pyridazin-3-one Structure

4-acetyl-2-(2-a...

1,2-Ethanedione,1,2-diphenyl-, 1-hydrazone Structure

1,2-Ethanedione...

Ethyl acetoacetate Structure

Ethyl acetoacetate

~%

5-acetyl-3,4-diphenyl-1H-pyridazin-6-one Structure

5-acetyl-3,4-di...

2,2'-dichloro-benzil-monohydrazone Structure

2,2'-dichloro-b...

~%

4-Pyridazinecarbonitrile, 5,6-bis(2-chlorophenyl)-2,3-dihydro-3-oxo- Structure

4-Pyridazinecar...

4-Pyridazinecarbonitrile, 5,6-bis(4-chlorophenyl)-2,3-dihydro-3-oxo- Structure

4-Pyridazinecar...

~20%

methyl 2-[3,4-bis(4-chlorophenyl)-5-cyano-6-oxopyridazin-1-yl]acetate Structure

methyl 2-[3,4-b...

(E)-4,4'-dichlorobenzil monohydrazone Structure

(E)-4,4'-dichlo...

~48%

4-Pyridazinecarbonitrile, 5,6-bis(4-chlorophenyl)-2,3-dihydro-3-oxo- Structure

4-Pyridazinecar...

ethyl 4-[3,4-bis(4-chlorophenyl)-5-cyano-6-oxopyridazin-1-yl]butanoate Structure

ethyl 4-[3,4-bi...

~29%

1(6H)-Pyridazinebutanoicacid, 3,4-bis(4-chlorophenyl)-5-cyano-6-oxo- Structure

1(6H)-Pyridazin...

4-Pyridazinecarbonitrile, 5,6-bis(4-chlorophenyl)-2,3-dihydro-3-oxo- Structure

4-Pyridazinecar...

~%

1(6H)-Pyridazinebutanoicacid, 3,4-bis(4-chlorophenyl)-5-cyano-6-oxo- Structure

1(6H)-Pyridazin...

Ethylene carbonate Structure

Ethylene carbonate

4-Pyridazinecarbonitrile, 5,6-bis(2-chlorophenyl)-2,3-dihydro-3-oxo- Structure

4-Pyridazinecar...

~80%

4-Pyridazinecarbonitrile,5,6-bis(2-chlorophenyl)-2,3-dihydro-2-(2-hydroxyethyl)-3-oxo- Structure

4-Pyridazinecar...

4-acetyl-5,6-bis(4-chlorophenyl)-2-(2-aminoethyl)-2H-pyridazin-3-one Structure

4-acetyl-5,6-bi...

~%

N-[2-[5-acetyl-3,4-bis(4-chlorophenyl)-6-oxo-pyridazin-1-yl]ethyl]acetamide Structure

N-[2-[5-acetyl-...

N/A Structure

~34%

4-acetyl-5,6-bis(4-fluorophenyl)-2H-pyridazin-3-one Structure

4-acetyl-5,6-bi...

Ethylene carbonate Structure

Ethylene carbonate

4-acetyl-5,6-bis(4-fluorophenyl)-2H-pyridazin-3-one Structure

4-acetyl-5,6-bi...

~45%

4-acetyl-5,6-bis(4-fluorophenyl)-2-(2-hydroxyethyl)pyridazin-3-one Structure

4-acetyl-5,6-bi...

2-Methoxyethyl 4-methylbenzenesulfonate Structure

2-Methoxyethyl ...

4-Acetyl-5,6-bis(p-chlorophenyl)-2H-pyridazin-3-one Structure

4-Acetyl-5,6-bi...

~26%

3(2H)-Pyridazinone,4-acetyl-5,6-bis(4-chlorophenyl)-2-(2-methoxyethyl)- Structure

3(2H)-Pyridazin...

Ethylene carbonate Structure

Ethylene carbonate

4-Pyridazinecarbonitrile, 5,6-bis(3,4-dichlorophenyl)-2,3-dihydro-3-ox o- Structure

4-Pyridazinecar...

~26%

5,6-Bis(3,4-dichlorophenyl)-2-(2-hydroxyethyl)-3-oxo-2,3-dihydro-4-pyridazinecarbonitrile Structure

5,6-Bis(3,4-dic...

ethyl 5,6-bis(4-chlorophenyl)-2-(2-hydroxyethyl)-3-oxo-2,3-dihydropyridazine-4-carboxylate Structure

ethyl 5,6-bis(4...

~81%

5,6-bis(4-chlorophenyl)-2-(2-hydroxyethyl)-3-oxo-pyridazine-4-carboxylic acid Structure

5,6-bis(4-chlor...

Ethylene carbonate Structure

Ethylene carbonate

4-Pyridazinecarbonitrile, 5,6-bis(4-chlorophenyl)-2,3-dihydro-3-oxo- Structure

4-Pyridazinecar...

~59%

4-Pyridazinecarbonitrile, 5,6-bis(4-chlorophenyl)-2,3-dihydro-2-(2-hydroxyethyl)-3-oxo- Structure

4-Pyridazinecar...

1,2-Ethanedione,1,2-diphenyl-, 1-hydrazone Structure

1,2-Ethanedione...

~31%

3(2H)-Pyridazinone,4-(4-methoxyphenyl)-5,6-diphenyl- Structure

3(2H)-Pyridazin...

N/A Structure

~%

5,6-bis(4-chlorophenyl)-2-(2-hydroxyethyl)-3-oxo-pyridazine-4-carboxylic acid Structure

5,6-bis(4-chlor...