7190-52-5

Upstream product

• 5617-70-9 cycl-isopropylidene cyclopropane-1,1-dicarboxylate 
• 100-63-0 phenylhydrazine 
• 20730-02-3 propionic acid 2-phenylhydrazide 
• 4641-57-0 1-phenylpyrrolidin-2-one 
• 113407-65-1 N-nitroso-N-phenyl-γ-aminobutyric acid 
• 113407-64-0 N-phenyl-γ-aminobutyric acid hydrochloride 
• 39232-92-3 N-methyl-N-phenylhydrazine hydrochloride 
• 112933-57-0 propanoic acid, 2-(3-cyanopropyl)-2-phenyl hydrazide 
• 369361-08-0 4-(1-phenylhydrazino)butanoic acid 
• 61446-43-3 tetrahydro-1-phenyl-3,6-pyridazinedione 

Downstream Products

• 24398-61-6 2,3,4,5-tetrahydro-2,6-diphenylpyridazine 
• 75343-38-3 3-(4-Fluoro-phenyl)-1-phenyl-1,4,5,6-tetrahydro-pyridazine 
• 73747-25-8 4-(phenylamino)butyronitrile 
• 112933-58-1 3-chloro-1,4,5,6-tetrahydro-1-phenylpyridazine 

Relevant academic research and scientific papers

A convenient synthesis of 1-aryl- and 1-alkyl-1,4,5,6-tetrahydropyridazin-3(2H)-ones

Aryl- and alkylhydrazines react with readily available cyclopropanedicarboxylate (2) in refluxing acetonitrile to afford the corresponding 1-substituted 1,4,5,6-tetrahydropyridazin-3(2H)-ones (5) directly via nitrogen-carbon bond formation, cyclization and decarboxylation of the cyclized intermediates.

5-lipoxygenase inhibitors: The synthesis and structure-activity relationships of a series of 1-phenyl-3-pyrazolidinones

A series of analogues of the 5-lipoxygenase inhibitor 1-phenyl-3-pyrazolidinone (phenidone, 1a) has been prepared via two complementary new synthetic methods. The reaction of various electrophiles with the dianion of 1a or with an N-silylpyrazolidinone anion gave the desired 4-substituted pyrazolidinones (Scheme I and II). A new procedure was developed for the resolution of 4-substituted pyrazolidinones (Scheme V). A regression study on 21 compounds in this series showed a correlation of increased inhibitor potency (pIC50) with increased compound lipophilicity (log P) and with an N-phenyl electronic effect as measured by the 13C NMR chemical shift parameter CNMR1' (R2 = 0.79). The most potent 5-lipoxygenase inhibitor in this series was 4-(ethylthio)-1-phenyl-3-pyrazolidinone (1n) with an IC50 of 60 nM. Another member of this series, 4-(2-methoxyethyl)-1-phenyl-3-pyrazolidinone (1f, IC50 = 0.48 μM), although less potent than 1n, was better tolerated in the whole animal relative to phenidone (1a) and also displayed good oral activity in two models of 5-lipoxygenase inhibition. On the basis of a structure-activity relationship study, a mechanism for the inhibition of 5-lipoxygenase by this class of inhibitors was proposed.

PREPARATION OF N-ARYLAMINO-2-PYRROLIDONES FROM ARYLHYDRAZIDES OF γ-CHLOROBUTYRIC ACID

Intramolecular alkylation of the arylhydrazides of γ-chlorobutyric acid in the presence of sodium ethoxide leads to the formation of N-arylamino-2-pyrrolidones.The direction of the reaction is not altered by the absence of a substituent on the aniline nitrogen atom.In the case of a p-nitrophenyl-hydrazide, O-alkylation is observed.

1,4,5,6-TETRAHYDRO-1-PHENYLPYRIDAZIN-3(2H)-ONE, A HOMOLOGUE OF PHENIDONE

The title compound is synthesised in 3 steps from phenyl hydrazine, and its properties are reported.