The reaction of β-amino-α,γ-dicyanocrotononitrile with acetophenone: Synthesis of pyridine, pyridazine and thiophene derivatives with antimicrobial activities

Mohareb R.M.; El-Sharkawy K.A.; Sherif S.M.

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The reaction of β-amino-α,γ-dicyanocrotononitrile with acetophenone: Synthesis of pyridine, pyridazine and thiophene derivatives with antimicrobial activities

Mohareb R.M.; El-Sharkawy K.A.; Sherif S.M.

Full Text link: https://t.ly/73qV2

Date issued: 2008

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Doi: https://doi.org/10.2478/v10007-008-0030-3 PubMed ID 19103577

Series Info: Acta Pharmaceutica
58

Type: Article

Keywords: Antimicrobial activity , Isoxazole , Pyridazine , Pyridine , Thiophene , 2 [amino (2,3 dihydro 3 imino 2,5 diphenylpyridazin 4 yl)methylene]malononitrile , 2 [amino [2,3 dihydro 3 imino 2 (3 cyano 4',5',6',7' tetrahydrobenzo[b]thieno 2 yl) 5 phenylpyridazin 4 yl]methylene]malononitrile , 2 [amino [2,3 dihydro 3 imino 2 (4' chlorophenyl) 5 phenylpyridazin 4 yl]methylene]malononitrile , 2 [amino [2,3 dihydro 3 imino 2 (ethyl 4',5',6',7' tetrahydrobenzo[b]thiopheno 3 carboxylato 2 yl) 5 phenylpyridazin 4 yl]methylene]malononitrile , 2 amino 4 phenyl 1,1,3 tricyano 6 (2' hydroxyphenyl)hexa 1,3,5 triene , 2 amino 4 phenylpenta 1,3 diene 1,1,3 tricarbonitrile , 2 amino 4,6 diphenyl 1,1,3 tricyanohexa 1,3,5 triene , 2,4 diamino 5,7 diphenylquinoline 3,8 dicarbonitrile , 5 (2 phenylhydrazono) 2 amino 4 phenylpenta 1,3 diene 1,1,3 tricarbonitrile , 5 (2,4 chlorophenylhydrazono) 2 amino 4 phenylpenta 1,3 diene 1,1,3 tricarbonitrile , 5 (3' cyano 4',5',6',7' tetrahydrobenzo[b]thieno 2 hydrazono) 2 amino 4 phenylpenta 1,3 diene 1,1,3 tricarbonitrile , 5 (ethyl 4',5',6',7' tetrahydrobenzo[b]thiopheno 3 carboxylato 2 hydrazono) 2 amino 4 phenylpenta 1,3 diene 1,1,3 tricarbonitrile , acetophenone , aldehyde , alpha cyano beta amino beta (2 amino 3 cyano 4,6 diphenylbenzen 1 yl)acrylonitrile , alpha cyano beta amino beta (2 amino 3 ethoxycarbonyl 4,6 diphenylbenzen 1 yl)acrylonitrile , beta amino alpha,gamma dicyanocrotononitrile , cyanomethylene derivative , diazonium compound , ethyl 2,4 diamino 5,7 diphenylquinoline 3 nitrilo 8 carboxylate , hydrazine derivative , hydroxylamine , isoxazole derivative , nitrile , pyrazole derivative , pyridazine derivative , pyridine derivative , sulfur , thiophene derivative , unclassified drug , unindexed drug , antibacterial activity , antifungal activity , antimicrobial activity , article , Bacillus cereus , Bacillus subtilis , Candida albicans , chemical reaction , controlled study , cyclization , drug potency , drug screening , drug synthesis , Escherichia coli , minimum inhibitory concentration , nonhuman , polymerization , reaction analysis , structure activity relation , structure analysis , Acetophenones , Anti-Infective Agents , Nitriles , Pyridazines , Pyridines , Structure-Activity Relationship , Thiophenes

Abstract:

Condensation of ?-amino-?,?-dicyanocrotononitrile (1) with acetophenone gave 2-amino-4-phenylpenta-1,3-diene-1,1,3-tricarbonitrile (2). The latter product was used in a series of heterocyclization reactions with different reagents such as diazonium salts, hydrazines, hydroxylamines and elemental sulfur to give pyridazine, pyrazole, isoxazole and thiophene derivatives, respectively. On the other hand, it gave pyridine derivatives with aromatic aldehydes folowed by reaction with cyanomethylene reagents. The MIC values for the newly synthesized product were measured against E. coli, B. cereus, B. subtilis and C. albicans.