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.Department of ChemistryFaculty of ScienceCairo UniversityGizaEgypt; Department of Organic ChemistryFaculty of PharmacyOctober University for Modern Sciences and Arts (MSA)OctoberEgypt2020-01-252020-01-25200813300075https://doi.org/10.2478/v10007-008-0030-3PubMed ID 19103577https://t.ly/73qV2ScopusCondensation 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.EnglishAntimicrobial activityIsoxazolePyridazinePyridineThiophene2 [amino (2,3 dihydro 3 imino 2,5 diphenylpyridazin 4 yl)methylene]malononitrile2 [amino [2,3 dihydro 3 imino 2 (3 cyano 4',5',6',7' tetrahydrobenzo[b]thieno 2 yl) 5 phenylpyridazin 4 yl]methylene]malononitrile2 [amino [2,3 dihydro 3 imino 2 (4' chlorophenyl) 5 phenylpyridazin 4 yl]methylene]malononitrile2 [amino [2,3 dihydro 3 imino 2 (ethyl 4',5',6',7' tetrahydrobenzo[b]thiopheno 3 carboxylato 2 yl) 5 phenylpyridazin 4 yl]methylene]malononitrile2 amino 4 phenyl 1,1,3 tricyano 6 (2' hydroxyphenyl)hexa 1,3,5 triene2 amino 4 phenylpenta 1,3 diene 1,1,3 tricarbonitrile2 amino 4,6 diphenyl 1,1,3 tricyanohexa 1,3,5 triene2,4 diamino 5,7 diphenylquinoline 3,8 dicarbonitrile5 (2 phenylhydrazono) 2 amino 4 phenylpenta 1,3 diene 1,1,3 tricarbonitrile5 (2,4 chlorophenylhydrazono) 2 amino 4 phenylpenta 1,3 diene 1,1,3 tricarbonitrile5 (3' cyano 4',5',6',7' tetrahydrobenzo[b]thieno 2 hydrazono) 2 amino 4 phenylpenta 1,3 diene 1,1,3 tricarbonitrile5 (ethyl 4',5',6',7' tetrahydrobenzo[b]thiopheno 3 carboxylato 2 hydrazono) 2 amino 4 phenylpenta 1,3 diene 1,1,3 tricarbonitrileacetophenonealdehydealpha cyano beta amino beta (2 amino 3 cyano 4,6 diphenylbenzen 1 yl)acrylonitrilealpha cyano beta amino beta (2 amino 3 ethoxycarbonyl 4,6 diphenylbenzen 1 yl)acrylonitrilebeta amino alpha,gamma dicyanocrotononitrilecyanomethylene derivativediazonium compoundethyl 2,4 diamino 5,7 diphenylquinoline 3 nitrilo 8 carboxylatehydrazine derivativehydroxylamineisoxazole derivativenitrilepyrazole derivativepyridazine derivativepyridine derivativesulfurthiophene derivativeunclassified drugunindexed drugantibacterial activityantifungal activityantimicrobial activityarticleBacillus cereusBacillus subtilisCandida albicanschemical reactioncontrolled studycyclizationdrug potencydrug screeningdrug synthesisEscherichia coliminimum inhibitory concentrationnonhumanpolymerizationreaction analysisstructure activity relationstructure analysisAcetophenonesAnti-Infective AgentsNitrilesPyridazinesPyridinesStructure-Activity RelationshipThiophenesThe reaction of β-amino-α,γ-dicyanocrotononitrile with acetophenone: Synthesis of pyridine, pyridazine and thiophene derivatives with antimicrobial activitiesArticlehttps://doi.org/10.2478/v10007-008-0030-3PubMed ID 19103577