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Abstract
A series of novel (E)-4-(4-(3,3-dimethyltriaz-1-en-1-yl)phenyl)-N-phenylpyrimidin-2-amine derivatives have been synthesized from the condensation of (E)-3-(dimethylamino)-1-(4-(E)-3,3-dimethyltriaz-1-en-1-yl)phenyl)prop-2-en-1-one with several guanidinium hydro-chloride. The newly synthesized compounds were examined for in vitro antimicrobial activity against some antibacterial and fungal strains. The synthesized compounds were characterized by 1H NMR, 13C NMR, IR, mass and elemental analyses.
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References
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References
T.M. Belete, Novel Targets to Develop New Antibacterial Agents and Novel Alternatives to Antibacterial Agents, Human Microbiome J., 11, 100052 (2019); https://doi.org/10.1016/j.humic.2019.01.001
I.C. Zampini, S. Cuello, M.R. Alberto, R.M. Ordoñez, R.D. Almeida, E. Solorzano and M.I. Isla, Antimicrobial Activity of Selected Plant Species from “the Argentine Puna” against Sensitive and Multi-Resistant Bacteria, J. Ethnopharmacol., 124, 499 (2009); https://doi.org/10.1016/j.jep.2009.05.011
A.P. Keche, G.D. Hatnapure, R.H. Tale, A.H. Rodge, S.S. Birajdar and V.M. Kamble, A Novel Pyrimidine Derivatives with Aryl Urea, Thiourea and Sulfonamide Moieties: Synthesis, Anti-inflammatory and Antimicrobial Evaluation, Bioorg. Med. Chem. Lett., 22, 3445 (2012); https://doi.org/10.1016/j.bmcl.2012.03.092
D.B. Kimball and M.M. Haley, Triazenes: A Versatile Tool in Organic Synthesis, Angew. Chem. Int. Ed., 41, 3338 (2002); https://doi.org/10.1002/1521-3773(20020916)41:18<3338::AID-ANIE3338>3.0.CO;2-7
A.P. Francisco, E. Mendes, A.R. Santos and M.J. Perry, Anticancer Triazenes: from Bioprecursors to Hybrid Molecules, Curr. Pharm. Des., 25, 1623 (2019); https://doi.org/10.2174/1381612825666190617155749
B. Shankar, P. Jalapathi, B. Saikrishna, S. Perugu and V. Manga, Synthesis, Anti-microbial Activity, Cytotoxicity of Some Novel Substituted (5-(3-(1H-Benzo[d]imidazol-2-yl)-4-hydroxybenzyl)benzofuran-2-yl)(phenyl)methanone Analogs, Chem. Cent. J., 12, 1 (2018); https://doi.org/10.1186/s13065-017-0364-3
J. Vajs, C. Proud, A. Brozovic, M. Gazvoda, A. Lloyd, D.I. Roper, M. Osmak, J. Košmrlj and C.G. Dowson, Diaryltriazenes as Antibacterial Agents against Methicillin Resistant Staphylococcus aureus (MRSA) and Mycobacterium smegmatis, Eur. J. Med. Chem., 127, 223 (2017); https://doi.org/10.1016/j.ejmech.2016.12.060
R.K. Rawal, R. Tripathi, S.B. Katti, C. Pannecouque and E. De Clercq, Synthesis and Evaluation of 2-(2,6-Dihalophenyl)-3-pyrimidinyl-1,3-thiazolidin-4-one Analogues as Anti-HIV-1 Agents, Bioorg. Med. Chem., 15, 3134 (2007); https://doi.org/10.1016/j.bmc.2007.02.044
A. Karimian and H. Karimian, Synthesis of New Derivatives of 4-(4-methyl-5H-pyrimido[4,5-b][1,4]thiazin-2-yl)morpholine and 4-methyl-2-(piperidin-1-yl)-5H-pyrimido[4,5-b][1,4]thiazine, J. Chem. Res., 41, 406 (2017); https://doi.org/10.3184/174751917X14967701767049
S. Schenone, C. Brullo, O. Bruno, F. Bondavalli, L. Mosti, G. Maga, E. Crespan, F. Carraro, F. Manetti, C. Tintori and M. Botta, Synthesis, Biological Evaluation and Docking Studies of 4-Amino Substituted 1H-pyrazolo[3,4-d]Pyrimidines, Eur. J. Med. Chem., 43, 2665 (2008); https://doi.org/10.1016/j.ejmech.2008.01.034
H.A.S. Abbas, W.A. El Sayed and N.M. Fathy, Synthesis and Antitumor Activity of New Dihydropyridine Thioglycosides and their Correspon-ding Dehydrogenated Forms, Eur. J. Med. Chem., 45, 973 (2010); https://doi.org/10.1016/j.ejmech.2009.11.039
B.S. Holla, M. Mahalinga, M.S. Karthikeyan, P.M. Akberali and N.S. Shetty, Synthesis of Some Novel Pyrazolo[3,4-d]pyrimidine Derivatives as Potential Antimicrobial Agents, Bioorg. Med. Chem., 14, 2040 (2006); https://doi.org/10.1016/j.bmc.2005.10.053
M.S. Mohamed, S.M. Awad and A.I. Sayed, Synthesis of Certain Pyrimidine Derivatives as Antimicrobial Agents and Anti-Inflammatory Agents, Molecules, 15, 1882 (2010); https://doi.org/10.3390/molecules15031882
T. Ozben, Mechanisms and Strategies to Overcome Multiple Drug Resistance in Cancer, FEBS Lett., 580, 2903 (2006); https://doi.org/10.1016/j.febslet.2006.02.020
L.K. Gediya and V.C. Njar, Promise and Challenges in Drug Discovery and Development of Hybrid Anticancer Drugs, Expert Opin. Drug Discov., 4, 1099 (2009); https://doi.org/10.1517/17460440903341705
T. Isobe, K. Fukuda, Y. Araki and T. Ishikawa, Modified Guanidines as Chiral Superbases: The First Example of Asymmetric Silylation of Secondary Alcohols, Chem. Commun., 243 (2001); https://doi.org/10.1039/b009173l
M. Abdul-Ghan, S.N. Khattab, A.M. El-Massry, A. El-Faham and A. Amer, A Novel and Direct Method for the Preparation of 4-Amino-1,1,3,3-tetrasubstttuted Guanidines and of [1,2,4]Triazolo-Fused Heterocyclic Derivatives, Org. Prep. Proced. Int., 36, 121 (2004); https://doi.org/10.1080/00304940409355382
A.S. Shawali, T.A. Farghaly and A.R. Al-Dahshoury, Synthesis, Reactions and Antitumor Activity of New p-Aminovinyl 3-pyrazolyl Ketones, ARKIVOC, 88 (2009); http://dx.doi.org/10.3998/ark.5550190.0010.e08
P. Ravula, H.B. Vamaraju, M. Paturi, S. Bodige, K.C. Gulipalli and J.N. Narendra Sharath Chandra, Design, Synthesis, and Docking Studies of Novel Dimethyl Triazene Incorporated Thiazolyl Pyrazolines for Anticancer Activity, J. Heterocycl. Chem., 55, 1313 (2018); https://doi.org/10.1002/jhet.3163
J. Zimmermann, E. Buchdunger, H. Mett, T. Meyer, N.B. Lydon and P. Traxler, Phenylamino-pyrimidine (PAP) Derivatives: A New Class of Potent and Highly Selective PDGF-Receptor Autophosphorylation Inhibitors, Bioorg. Med. Chem. Lett., 6, 1221 (1996); https://doi.org/10.1016/0960-894X(96)00197-7