Synthesis of Novel Heteropolycyclic Nitrogen Systems Bearing Fluorine Substituted Pyrazolo[3,4-d] Pyrimidine Derived from Polyfunctional π-Acceptor Compounds and Guanidine as Fungicidal Probes — Oak Academic Publishing
Research ArticleOpen AccessGoogle Scholar indexed
Synthesis of Novel Heteropolycyclic Nitrogen Systems Bearing Fluorine Substituted Pyrazolo[3,4-d] Pyrimidine Derived from Polyfunctional π-Acceptor Compounds and Guanidine as Fungicidal Probes
Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia
,
Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia
1 Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia
2 Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia
Novel heteropolycyclic nitrogen systems bearing fluorine substituted pyrazolo[3,4- d ] pyrimidine moiety have been synthesis by the interaction between N ’-heteroaryl guanidine 4 with polyfunctional π-acceptors in different media and condition. The structures of the synthesis compounds were established by spectroscopic analysis and evaluated as antifungal probes in various concentration.
Abdul-Rahman, R., Bakhotmah, D. and Fakhorji, M. (2017) Synthesis and Chemical Reactivity of Some New Fluorine Substituted Pyrazolopyrimidine Derivatives and Their Effect on Cellobiase Activity Produced by Fungi. World Journal of Organic Chemistry, 5, 1-5. http://pubs.sciepub.com/wjoc/5/1/1
Bakhotmah, D., Abdel-Rahman, R., Fakhrji, M. and kamal, A. (2017) Synthesis of Some New Fluorinated Fused Heteropolycyclic Nitrogen Systems Containing Pyrazo-lo[3,4-d]pyrimidines Moiety and Their Effects on Cellobiase Activity Produced by Aspergillusnidulans Fungi. Modern Organic Chemistry, 2, 172-178.
Bakhotmah, D. and Abdel-Rahman, R. (2017) Synthesis and Structural Determination of Novel Fluorinated Steroidal Spi-ro(pyrazolo[4,3-e][1,2,4]triazin-3’-yl) Derivatives as Affecting Enzymatic Agents. Letters in Organic Chemistry, 14, 134-140. https://doi.org/10.2174/1570178614666161230143228
Shamroukh, A.H., Rashad, A.E., Ali, H.S. and Abdel-Megeid, F.M.E. (2013) Some New Pyrazole and Pyrazolopyrimidines: Synthesis and Antimicrobial Evaluation. Journal of Heterocyclic Chemistry, 50, 758-765. https://doi.org/10.1002/jhet.1550
Bakavoli, M., Bagherzadeh, G., Vaseghifar, M., Shiri, A., Pordel, M., Mashreghi, M., Pordeli, P. and Araghi, M. (2010) Molecular Iodine Promoted Synthesis of New Pyrazolo[3,4-d]pyrimidine Derivatives as Potential Antibacterial Agents. European Journal of Medicinal Chemistry, 45, 647-650. https://doi.org/10.1016/j.ejmech.2009.10.051
Yuan, L., Song, C., Li, C., Li, Y., Dong, L. and Yin, S. (2013) Synthesis and Biological Evaluation of Pyrazolo[4,3-d]pyrimidine Analogues. European Journal of Medicinal Chemistry, 67, 152-157. https://doi.org/10.1016/j.ejmech.2013.05.019
Shamroukh, A.H., Rashad, A.E., Abdel-Megeid, R.E., Ali, H.S. and Ali, M.M. (2014) Some Pyrazole and Pyrazolo[3,4-d]pyrimidine Derivatives: Synthesis and Anticancer Evaluation. Archiv der Pharmazie, 347, 559-565. https://doi.org/10.1002/ardp.201400064
Ismail, F.M.D. (2002) Important Fluorinated Drugs in Experimental and Clinical Use. Journal of Fluorine Chemistry, 118, 27-33. https://doi.org/10.1016/S0022-1139(02)00201-4
Ojima, I., McCarthy, J.R. and Welch, J.T. (1996) Biomedical Frontiers of Fluorine Chemistry. American Chemical Society, 639, 372. https://doi.org/10.1021/bk-1996-0639
Abdel-Rahman, R., Makki, M.S.T., Ali, T.E.-S. and Ibrahim, M.A. (2010) 1,2,4-Triazine Chemistry Part I: Orientation of Cyclization Reactions of Functionalized 1,2,4-Triazine Derivatives. European Journal of Chemistry, 1, 236-245. https://doi.org/10.1021/bk-1996-0639
Abdel-Rahman, R. and Ab-del-Monem, W. (2007) Chemical Reactivity of 3-Hydra-zino-5,6-diphenyl-1,2,4-triazine towards Pi-Acceptors Activated Carbonitriles. In-dian Journal of Chemistry, 46, 838-846.
Abdel-Monem, W. and Ab-del-Rahman, R. (2006) Synthesis of 3-Heteroaryl-6,7-diphenyl-1,2,4-triazo-lo[4, 3-b] [1,2,4]tria-zines and Their Biological Activities. International Journal of Chemistry, 16, 1-14.
Ibrahim, M., Abdel-Rahman, R., Abdel-Halim, A., Ibrahim, S. and Allimony, H. (2009) Synthesis, Chemical Reactivity and Fungicidal Activity of Pyrido[1,2-b] [1,2,4]triazine derivatives. Journal of the Brazilian Chemical Society, 20, 1275-1286. https://doi.org/10.1590/S0103-50532009000700012
Ibrahim, M., Abdel-Rahman, R., Abdel-Halim, A., Ibrahim, S. and Allimony, H. (2008) Synthesis and Antifungal Activity of Novel Polyheterocyclic Compounds Containing Fused 1,2,4-Triazine Moiety. Arkivoc, 16, 202-215.
Makki, M., Bakhotmah, D., Abdel-Rahman, R. and Aqlan, F. (2018) New Route to Synthesize Fluorine Substituted Lamotrigine Drug Analogues as an Anti-Inflammatory Agent. Current Organic Synthesis, 15, 116-125. https://doi.org/10.2174/1570179414666170509151123
Khan, S.A., Asiri, A.M., Abdel-Rahman, R., Elroby, S.A., Aqlan, F.M.S., Wani, M.Y. and Sharma, K. (2017) Multistep Synthesis of Fluorine-Substituted Pyrazolopyrimidine Derivatives with Higher Antibacterial Efficacy Based on in Vitro Molecular Docking and Density Functional Theory. Journal of Heterocyclic Chemistry, 54, 3099-3107. https://doi.org/10.1002/jhet.2923
Bakhotmah, D. (2019) Synthesis and Chemical Reactivity of 6-amino-4-(4’-fluoro-phe-nyl)-1-phenyl-3-methyl-pyrazolo[3,4-d]pyrimidine towards Some Activated Elec-tophiles and Their Effect on Cellobiase Activity Produced by Some Fungi.
Munoz-Torrero, D., Mangoni, A.A., Guillou, C., Collina, S., VandenEynde, J.J., Rautio, J., Keseru, G.M., Hulme, C., Chibale, K., Luque, F.J., Karaman, R., Gutschow, M., Liu, H. and Ragno, R. (2017) Breakthroughs in Medicinal Chemistry: New Targets and Mechanisms, New Drugs, New Hopes. Molecules, 22, pii: E743.
Júnior, P.E.S., Rezende, L.C.D., Gimenes, J.P., Maltarollo, V.G., Dale, J., Trossini, G.H.G., Emery, F.S. and Ganesan, A. (2016) Synthesis of Two “Heteroaromatic Rings of the Future” for Applications in Medicinal Chemistry. RSC Advances, 6, 22777-22780. https://doi.org/10.1039/C6RA01099G
Bakhotmah, D. and Abdel-Rahman, R. (2016) A Review on the Synthesis and Chemistry of Bioactive Pyrazolines Bearing 1,2,4-Triazine Moieties. Mini-Reviews in Organic Chemistry, 13, 62-77. https://doi.org/10.2174/1570193X13666160225000114
Fang, X.J., Jeyakkumar, P., Avula, S.R., Zhou, Q. and Zhou, C.H. (2016) Design, Synthesis and Biological Evaluation of 5-Fluorouracil-Derived Benzimidazoles as Novel Type of Potential Antimicrobial Agents. Bioorganic & Medicinal Chemistry Letters, 26, 2584-2588. https://doi.org/10.1016/j.bmcl.2016.04.036
Ryu, J.H., Lee, J.A., Kim, S., Shin, Y.A., Yang, J., Han, H.Y., Son, H.J., Kim, Y.H., Sa, J.H., Kim, J.-S., Lee, J., Lee, J. and Park, H.-G. (2016) Discovery of 2-((R)-4-(2-Fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)-N-((1R,2s,3S,5S,7S)-5-hydroxyadamantan-2-yl)pyrimidine-4-carboxamide (SKI2852): A Highly Potent, Selective, and Orally Bioavailable Inhibitor of 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1). Journal of Medicinal Chemistry, 59, 10176-10189. https://doi.org/10.1021/acs.jmedchem.6b01122
Chamberlain, K. and Carter, G.A. (1980) The Fungitoxicity of Substituted 2-Phenyl-benzofurans. Pesticide Science, 11, 526-532. https://doi.org/10.1002/ps.2780110510