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

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dc.AffiliationOctober University for modern sciences and Arts (MSA)
dc.contributor.authorMohareb R.M.
dc.contributor.authorEl-Sharkawy K.A.
dc.contributor.authorSherif S.M.
dc.contributor.otherDepartment of Chemistry
dc.contributor.otherFaculty of Science
dc.contributor.otherCairo University
dc.contributor.otherGiza
dc.contributor.otherEgypt; Department of Organic Chemistry
dc.contributor.otherFaculty of Pharmacy
dc.contributor.otherOctober University for Modern Sciences and Arts (MSA)
dc.contributor.otherOctober
dc.contributor.otherEgypt
dc.date.accessioned2020-01-25T19:58:34Z
dc.date.available2020-01-25T19:58:34Z
dc.date.issued2008
dc.descriptionScopus
dc.description.abstractCondensation 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.en_US
dc.description.urihttps://www.scimagojr.com/journalsearch.php?q=19398&tip=sid&clean=0
dc.identifier.doihttps://doi.org/10.2478/v10007-008-0030-3
dc.identifier.doiPubMed ID 19103577
dc.identifier.issn13300075
dc.identifier.otherhttps://doi.org/10.2478/v10007-008-0030-3
dc.identifier.otherPubMed ID 19103577
dc.identifier.urihttps://t.ly/73qV2
dc.language.isoEnglishen_US
dc.relation.ispartofseriesActa Pharmaceutica
dc.relation.ispartofseries58
dc.subjectAntimicrobial activityen_US
dc.subjectIsoxazoleen_US
dc.subjectPyridazineen_US
dc.subjectPyridineen_US
dc.subjectThiopheneen_US
dc.subject2 [amino (2,3 dihydro 3 imino 2,5 diphenylpyridazin 4 yl)methylene]malononitrileen_US
dc.subject2 [amino [2,3 dihydro 3 imino 2 (3 cyano 4',5',6',7' tetrahydrobenzo[b]thieno 2 yl) 5 phenylpyridazin 4 yl]methylene]malononitrileen_US
dc.subject2 [amino [2,3 dihydro 3 imino 2 (4' chlorophenyl) 5 phenylpyridazin 4 yl]methylene]malononitrileen_US
dc.subject2 [amino [2,3 dihydro 3 imino 2 (ethyl 4',5',6',7' tetrahydrobenzo[b]thiopheno 3 carboxylato 2 yl) 5 phenylpyridazin 4 yl]methylene]malononitrileen_US
dc.subject2 amino 4 phenyl 1,1,3 tricyano 6 (2' hydroxyphenyl)hexa 1,3,5 trieneen_US
dc.subject2 amino 4 phenylpenta 1,3 diene 1,1,3 tricarbonitrileen_US
dc.subject2 amino 4,6 diphenyl 1,1,3 tricyanohexa 1,3,5 trieneen_US
dc.subject2,4 diamino 5,7 diphenylquinoline 3,8 dicarbonitrileen_US
dc.subject5 (2 phenylhydrazono) 2 amino 4 phenylpenta 1,3 diene 1,1,3 tricarbonitrileen_US
dc.subject5 (2,4 chlorophenylhydrazono) 2 amino 4 phenylpenta 1,3 diene 1,1,3 tricarbonitrileen_US
dc.subject5 (3' cyano 4',5',6',7' tetrahydrobenzo[b]thieno 2 hydrazono) 2 amino 4 phenylpenta 1,3 diene 1,1,3 tricarbonitrileen_US
dc.subject5 (ethyl 4',5',6',7' tetrahydrobenzo[b]thiopheno 3 carboxylato 2 hydrazono) 2 amino 4 phenylpenta 1,3 diene 1,1,3 tricarbonitrileen_US
dc.subjectacetophenoneen_US
dc.subjectaldehydeen_US
dc.subjectalpha cyano beta amino beta (2 amino 3 cyano 4,6 diphenylbenzen 1 yl)acrylonitrileen_US
dc.subjectalpha cyano beta amino beta (2 amino 3 ethoxycarbonyl 4,6 diphenylbenzen 1 yl)acrylonitrileen_US
dc.subjectbeta amino alpha,gamma dicyanocrotononitrileen_US
dc.subjectcyanomethylene derivativeen_US
dc.subjectdiazonium compounden_US
dc.subjectethyl 2,4 diamino 5,7 diphenylquinoline 3 nitrilo 8 carboxylateen_US
dc.subjecthydrazine derivativeen_US
dc.subjecthydroxylamineen_US
dc.subjectisoxazole derivativeen_US
dc.subjectnitrileen_US
dc.subjectpyrazole derivativeen_US
dc.subjectpyridazine derivativeen_US
dc.subjectpyridine derivativeen_US
dc.subjectsulfuren_US
dc.subjectthiophene derivativeen_US
dc.subjectunclassified drugen_US
dc.subjectunindexed drugen_US
dc.subjectantibacterial activityen_US
dc.subjectantifungal activityen_US
dc.subjectantimicrobial activityen_US
dc.subjectarticleen_US
dc.subjectBacillus cereusen_US
dc.subjectBacillus subtilisen_US
dc.subjectCandida albicansen_US
dc.subjectchemical reactionen_US
dc.subjectcontrolled studyen_US
dc.subjectcyclizationen_US
dc.subjectdrug potencyen_US
dc.subjectdrug screeningen_US
dc.subjectdrug synthesisen_US
dc.subjectEscherichia colien_US
dc.subjectminimum inhibitory concentrationen_US
dc.subjectnonhumanen_US
dc.subjectpolymerizationen_US
dc.subjectreaction analysisen_US
dc.subjectstructure activity relationen_US
dc.subjectstructure analysisen_US
dc.subjectAcetophenonesen_US
dc.subjectAnti-Infective Agentsen_US
dc.subjectNitrilesen_US
dc.subjectPyridazinesen_US
dc.subjectPyridinesen_US
dc.subjectStructure-Activity Relationshipen_US
dc.subjectThiophenesen_US
dc.titleThe reaction of β-amino-α,γ-dicyanocrotononitrile with acetophenone: Synthesis of pyridine, pyridazine and thiophene derivatives with antimicrobial activitiesen_US
dc.typeArticleen_US
dcterms.isReferencedByBolognese, A., Correale, G., Manfra, M., Lavecchia, A., Novellino, E., Pepe, S., Antitumor agents. 5. Synthesis, structure-activity relationships, and biological evaluation of dimethyl-5H-pyridophenoxazin-5-ones, tetrahydro-5H-benzopyridophenoxazin-5-ones, and 5H-benzopyridophenoxazin-5-ones with potent antiproliferative activity (2006) J. Med. Chem, 49, pp. 5110-5118. , DOI: 10.1021/jm0507451; Heimer, G., Rivlin-Etzion, M., Bar-Gad, I., Goldberg, J.A., Haber, S.N., Bergman, H., Dopamine replacement therapy does not restore the full spectrum of normal pallidal activity in the 1-methyl-4-phenyl-1,2,3,6-tetra-hydropyridine primate model of Parkinsonism (2006) J. Neurosci, 26, pp. 8101-8114. , DOI: 10.1523/JNEUROSCI.5140-05.2006; Powers, R., Copland, J.C., Germer, K., Mercier, K.A., Ramanathan, V., Revesz, P., Comparison of protein active site structures for functional annotation of proteins and drug design (2006) Proteins, 65, pp. 124-135. , DOI: 10.1002/prot.21092; Abdelrazek, F.M., Micheal, F.A., Mohamed, A.E., Synthesis and molluscicidal activity of some 1,3,4-triaryl-5-chloropyrazole, pyrano[2,3-c]pyrazole, pyrazolylphthalazine and pyrano[2,3--d]thiazole derivatives (2006) Arch. Pharm. (Weinheim), 339, pp. 305-312. , DOI: 10.1002/ardp.200500259; Abdelrazek, F.M., Fathy, A.D., A novel synthesis and molluscicidal activity of some functionally substituted pyridine, pyrido[3,2-c]pyridazine, and pyrido[3,2-c]pyridazino[2?,3?-a]quinazoline derivatives (2005) Arch. Pharm. (Weinheim), 338, pp. 329-334. , DOI: 10.1002/ardp.200400938; Alias, S., Andreu, R., Cerdan, M.A., Franco, S., Garin, J., Orduna, J., Romero, P., Villacampa, B., Synthesis, characterization and optical properties of merocyanines derived from malononitrile dimer (2007) Tetrahedron Lett, 48, pp. 6539-6542. , DOI: 10.1016/j.tetlet.2007.07.048; Wing, L.K., Behanna, H.A., Van Eldik, L.J., Watterson, D.M., Ralay, R.H., De novo and molecular target-independent discovery of orally bioavailable lead compounds for neurological disorders (2006) Curr. Alzheimer Res, 3, pp. 205-214. , DOI: 10.2174/156720506777632844; Rozsa, E., Obotka, H., Nagy, D., Farkas, T., Saa, K., Vecsei, L., Toldi, J., The pentylenetetrazole-iduced acivity in the hippocampus can be inhibited by the conversion of 1-kynurenine to kynurenic acid: An in vitro study (2008) Brain Res. Bull, 76, pp. 474-479. , DOI: 10.1016/j.brainresbull.2007.12.001; Szarics, E., Simon, A., Visy, J., Simon-Trompler, E., Banka, Z., Heja, L., Harsing, L.G., Kardos, J., Cyclothiazide binding to the GABAA receptor (2008) Neurosci. Lett, 439, pp. 66-69. , DOI: 10.1016/j.neulet.2008.04.092; Odlo, K., Hentzen, J., Chabert, J.F., Ducki, S., Gani, O.A., Sylte, I., Skrede, M., Hanse, T.V., 1,5-Disubstituted 1,2,3-triazole as cis-restricted analogues of combrestastatin A-4: Synthesis, molecular modeling and evaluation as cytotoxic agents and inhibitors of tubulin (2008) Bioorg. Med. Chem, 16, pp. 4829-4838. , DOI: 10.1016/j.bmc.2008. 03.049; Zhao, H., Serby, M.D., Xin, Z., Szczepankiewicz, B.G., Liu, M., Kosogof, C., Liu, B., Liu, G., Discovery of potent highly selective, and orally bioavailable pyridine carboxamide c-Jun NH2-terminal kinase inhibitors (2006) J. Med. Chem, 27, pp. 4455-4458. , DOI: 10.1021/jm0604651; Muranaka, K., Sano, A., Ichikawa, S., Mastsuda, A., Synthesis of Hsp89 inhibitor dimmers as potential antitumer agents (2008) Bioorg. Med. Chem, 16, pp. 5862-5870. , DOI: 10.1016/j.bmc.2008.04.070; A. Burguete, E. Pontiki, D. H. Litina, R. Villar, E. Vicente, B. Solano, S. Ancizu, S. Silanes, I. Aldana, A. Monge, Y. Maruyama, K. Anami and Y. Kotoh, Synthesis and anti-flammatory/antioxidant activities of some new ring substituted 3-phenyl-1-(1,4-di-N-oxide quinioxalin-2-yl)-2--propen-1-one derivatives and of their 4,5-dihydro-(1H)-pyrazole analogues, Bioorg. Med. Chem. Lett. 17 (2007) 6439-6443; DOI: 10.1016/j.bmcl.2007.10. 002; Hirokawa, Y., Kinoshita, H., Tanaka, T., Nakamura, T., Fujimoto, K., Kashimoto, S., Kojima, T., Kato, S., Pleuromutilin derivatives having a putine ring. Part 1: New compounds with promising antibacterial activity against resistant Gram-positive pathogens (2008) Bioorg. Med. Chem. Lett, 18, pp. 3556-3561. , DOI: 10.1016/j.bmcl.2008.05.011; Palmer, A.M., Grobbel, B., Brehm, C., Zimmermann, P.J., Buhr, W., Feth, M.O., Holst, H.C., Simon, W.A., Preparation of tetrahydroimidazo[2,1-a] isoquinolines and their use as inhibitors of gastric acid secretion (2007) Bioorg. Med. Chem, 15, pp. 7647-7660. , DOI: 10.1016/j.bmc.2007.08.065; Leon, R., Rois, C., Contelles, J.M., Lopez, M.G., Barcia, A.G., Villaroya, M., Synthesis of 6-amino-1,4-dihydropyridines that prevent calcium overload and neuronal death (2008) Eur. J. Med. Chem, 43, pp. 668-674. , DOI: 10.1016/j.ejmech.2007.06.001; J. Z. Yang, Y. Chen, A. M. Zhu, Q. L. Liu and J. Y. Wu, Analyzing diffusion behaviour of methanol/water through MFI membranes by molecular simulation, J. Membrane Sci. 328 (2008) 327-333; DOI: 10.1016/j.memsci.2008,02,059; Y. Z. Povstenko, Fractional radial diffusion ion in a cylinder, J. Mol. Liquids, 137 (2008) 46-50; DOI: 10.1016/j.molliq.2007,03.006; Sterk, H., Mittelbach, M., The relaxational behaviour of nitrile groups (1985) J. Mag. Res, 62, pp. 175-181. , DOI: 10.1016/0022-2364(85)90051- 4; McKibben, B.P., Cartwright, C.H., Castelhano, A.L., Practicle synthesis of tetrasubstituted thiophenes for use in compound libraries (1999) Tetrahedron Lett, 40, pp. 5471-5474. , DOI: 10.1016/S0040-4039(99) 01108-9; Milart, P., Wilamowski, J., Sepiol, J.J., Synthesis of di- and triamino-1,1?:3?,1?-terphenyls from arylethylidene- and arylidenemalonodinitriles (1998) Tetrahedron, 54, pp. 15643-15656. , DOI: 10.1016/S0040-4020(98)00978-8
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