Synthesis of New Fluorinated Fused Heteropolycyclic Nitrogen Systems Containing a Pyrazolotriazine Moiety as Antimicrobial Agents Part I — Oak Academic Publishing
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Synthesis of New Fluorinated Fused Heteropolycyclic Nitrogen Systems Containing a Pyrazolotriazine Moiety as Antimicrobial Agents Part I
Department of Chemistry, Faculty of Science, King Abdul Aziz University, Jeddah, KSA
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Department of Chemistry, Faculty of Science, King Abdul Aziz University, Jeddah, KSA
1 Department of Chemistry, Faculty of Science, King Abdul Aziz University, Jeddah, KSA
2 Department of Chemistry, Faculty of Science, King Abdul Aziz University, Jeddah, KSA
A simple route to synthesize novel fluorinated fused hetero-polycyclic nitrogen systems containing a pyrazolotriazine moiety ( 5 , 8 , 11 ) have been deduced from cyclization of 2-aminothiocarbonyl-5-arylidene-3-phenyl-1,2,4-triazin-6(1H)one ( 2 ) with diethoxy-phosphine, diethyl carbonate and/or diethyl oxalate in boil THF followed by cyclo condensation with aryl sulfonic acid hydrazide in EtOH/piperidine and finally fluorination with trifluoroethyl acetate. Structures of the products have been established from their elemental analysis and spectral measurements. The antimicrobial activity of the targets has also been evaluated.
Abdel-Rahman, R.M. and Saad, H.A. (2016) Synthesis and Chemical Behavior of 1,2,4-Triazine Derivatives Bearing Phosphorus Amides as Donor-Acceptors: A Review. Current Organic Synthesis, 13, 408-425. https://doi.org/10.2174/1570179412666150905001956
Garcia-Hemandez, Z., Floress-Parra, A., Grery, J.M., Ramos-Organilo, A. and Contreras, R. (2006) 2-Amino Benzothiazole Phosphorus Amides: Molecular and Supramolecular Structures, hydrogen Bonds and Sulfur Donor-Acceptor Interaction. Polyhedron, 25, 1662-1672. https://doi.org/10.1016/j.poly.2005.11.018
Ali, T.E., Abdel-Rahman, R.M., Hanafy, F. and El-Edfawy, S.M. (2008) Synthesis and Molluscicidal Activity of Phosphorus Containing Heterocyclic Compounds Derived from 5,6-Bis(4-bromophenyl)-3-hydrazino-1,2,4-triazine. Phosphorus, Sulfur, and Silicon and the Related Elements, 183, 2565-2577. https://doi.org/10.1080/10426500801967864
Al-Romaizan, A.N., Makki, M.S.T. and Abdel-Rahman, R.M. (2014) Synthesis of New Fluorine/Phosphorus Substituted 6-(2’-Aminophenyl)-3-thioxo-1,2,4-triazin-5(2H,4H)one and their related Alkylated Systems as Molluscicidal Agents as against the Snails Responsible for Bilharzias Diseases. International Journal of Organic Chemistry, 4, 154-168. https://doi.org/10.4236/ijoc.2014.42017
Abdel-Rahman, R.M., Makki, M.S.T. and Al-Romizan, A.N. (2014) Synthesis of Novel Fluorine Substituted Isolated and Fused Heterobicyclic Nitrogen Systems Bearing 6-(2’-Phosphorylanilido)-1,2,4-Triazin-5-one Moiety as Potential Inhibitors towards WIV-1 Activity. International Journal of Organic Chemistry, 4, 247-268. https://doi.org/10.4236/ijoc.2014.44028
Zein, M.A. and El-Shenawy, A.I. (2016) An Efficient Synthesis of 1,2,4-Triazine-6-One Derivatives and Their In Vitro Anticancer Activity. International Journal of Pharmacology, 12, 188-194. https://doi.org/10.3923/ijp.2016.188.194
Al-Hussaini, A.S., El-Sayed, E.H. and Radwan, E.M. (2015) Synthesis of 2,3,5-Trisubstituted 1,2,4-Triazine-6-Ones as Potential Antitumor. Der Pharma Chemica, 7, 214-225. http://www.derpharmachemica.com/archive/dpc-volume-7-issue-11-year-2015.html
El-Hady, H.A. and El-Sakka, S.E. (2014) Synthesis and Antitumor Activity of Some 1,2,4-Triazine Derivatives. International Journal of Innovative Research in Science Engineering and Technology, 3, 10854-10860.
Abubshait, S.A. and Abubshait, H.A. (2012) Biological Activity and Mass Spectra Investigation of Synthesized 1,2,4-Triazine Derivatives. Journal of Chemical & Pharmaceutical Research, 4, 568-579. http://www.joccpr.com/articles/biological-activity-and-mass-spectra-investigation-of-synthesized-1-2-4triazine-derivatives.pdf
Abdullatif, M.H. (2016) Synthesis of Some Novel Compounds of Saccharinyl Acetic Acid Containing Nucleus and Evaluation of Their Biological Activities as Antimicrobial. Oriental Journal of Chemistry, 32, 567-574.
Shaikh, B.M., Chobe, S.S., Konda, S.G., Khandara, N.T., Chavan, S.A. and Dawane, B.S. (2010) An Efficient Synthesis and In Vitro Antimicrobial Activity of 1,2,4-Triazin-6-(5H)one Derivatives. Der Chemica Sinica, 1, 86-91.
Dawane, B.S., Kadam, S.N. and Shaikh, B.M. (2010) An Efficient Synthesis of 1,2,4-Triazine Derivatives and Their In Vitro Antimicrobial Activity. Der Pharmacia Letter, 2, 126-131.
Khalifa, M.M.A. (2006) Synthesis and Antimicrobial Evaluation of Novel 1,2,4-Triazine Derivatives. Oriental Journal of Chemistry, 24, 825-830.
Mulwad, V.V. and Satwe, D.S. (2006) Synthesis of Biological Active 4-[1-(2H)[1]-4- Hydroxy-2-oxo-benzopyran-3-yl)methylidene]-2-phenyl-4H-oxazol-5-ones and 1,2,4- Triazine-6-one and Its Derivatives. Indian Journal of Chemistry, 45, 1210-1215.
Hin, N., Duvall, B., Ferraris, D., Alt, J., Thomas, A.G., Rais, R., Raja, C., Wu, Y., Wozniak, K.M., Slusher, B.S. and Tsukamoto, T. (2015) 6-Hydroxy-1,2,4-Triazine-3,5-(2H,4H)-dione Derivatives as Novel D-Amino Acid Oxidase Inhibitors. Journal of Medicinal Chemistry, 58, 7258-7272. https://doi.org/10.1021/acs.jmedchem.5b00482
El-Abadelah, M.M., Abushamleh, A.S., Mossmer, C.M. and Voelter, W. (2002) Transitione Metal Complexes of Derivatized Chiral Dihydro-1,2,4-triazin-6-ones, Part IV. Synthesis and Structural Characterization of a Copper(II) Complexes L-3-acetyl-5-benzyl-1-phenyl-4,5-dihydro-1,2,4-triazin-6-one Oxime. Zeitschrift for Naturforschung B, 57, 547-551.
Abdel-Rahman, R.M. and Bakhotmah, D.A. (2016) Synthesis and Chemistry of Bioactive Pyrazolyl-1,2,4-Triazines. Mini Review in Organic Chemistry, 13, 62-77.
Makki, M.S.T., Abdel-Rahman, R.M. and Khan, K.A. (2014) Fluorine Substituted 1,2,4-Triazinones as Potential Anti-HIV-1 and CDK2 Inhibitor. Journal of Chemistry, 2014, Article ID 430573. https://doi.org/10.1155/2014/430573
Abdel-Rahman, R.M. (1999) Chemistry of Uncondensed 1,2,4-Triazines, Part III. Synthesis and Chemistry of Fluorine Containing Bioactive 1,2,4-Triazines Overview. Pharmazie, 54, 791-863.
Abdel-Rahman, R.M., Bakhotmah, D.A. 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.
Abdel-Rahman, R.M. (1992) Synthesis of Some New Fluorine Bearing Trisubstituted 3-Thioxo-1,2,4-triazin-5-ones as Potential Anticancer Agents. Farmaco, 47, 319.
Abdel-Rahman, R.M., Seada, M., Fawzy, M. and El-Baz, I. (1993) Synthesis of Some New Thioethers Bearing a 1,2,4-Triazine-3-hydrazones and Assays for Their Anti-cancer and Anti-Human Immune Virus Activities. Farmaco, 48, 391-406.
Abdel-Rahman, R.M., Morsy, J., Hanafy, F. and Amine, H.A. (1999) Synthesis of Heterobicyclic Nitrogen Systems Bearing the 1,2,4-Triazine Moiety as Anti-HIV and Anticancer Drugs-I. Pharmazie, 54, 347-351.
Abdel-Rahman, R.M., Morsy, J., El-Edfawy, S. and Amine, H.A. (1999) Synthesis of Some New Heterobicyclic Nitrogen Systems Bearing the 1,2,4-Triazine Moiety as Anti-HIV and Anticancer Drugs II. Pharmazie, 54, 667-671.
El-Gendy, Z., Morsy, J., Allimony, H., Abdel-Monem, W. and Abdel-Rahman, R.M. (2001) Synthesis of Some New Heterobicyclic Nitrogen Systems Bearing 1,2,4-Triazine Moiety as Anti-HIV and Anticancer Drug-III. Pharmazie, 56, 376.
El-Gendy, Z., Morsy, J., Allimony, H., Abdel-Monem, W. and Abdel-Rahman, R.M. (2003) Synthesis of Some New Heterobicyclic Nitrogen Systems Bearing 1,2,4-Triazine Moiety as Anticancer Drugs: Part IV. Phosphorus, Sulfur, and Silicon and the Related Elements, 178, 2055-2071. https://doi.org/10.1080/10426500390228738
Bakhotmah, D.A. and Abdel-Rahman, R.M. (2017) Synthesis and Structural Determination of Novel Fluorinated Steroidal Spiro(pyrazolo[4,3-e][1,2,4]triazin-3’-yl) Derivatives as Affecting Enzymatic Agents. Letter in Organic Chemistry, 14, 134-140. https://doi.org/10.2174/1570178614666161230143228
Abdel-Rahman, R.M., Angawi, R.F. and Al-Mehmady, A.R. (2017) Synthesis and Biological Evaluation of Fluorine-Substituted pyrazolo[4,3-e][1,2,4]triazines as Purine Analogues. Journal of Saudi Chemical Society, 21, 495-503. https://doi.org/10.1016/j.jscs.2016.11.004
Aqlan, F.M., Makki, M.S.T. and Abdel-Rahman, R.M. (2016) Synthesis, Spectroscopic Studies of Fluorinated Pyrimido-1,2,4-Triazines: Protective Effect against Some Plant Pathogenic Fungi. Journal of Heterocyclic Chemistry, 35, 1310-1317. https://doi.org/10.1002/jhet.2386
Muanza, D.N., Kim, B.W., Euler, K.L. and Dan Williams, L. (1994) Antibacterial and Antifungal Activities of Nine Medicinal Plants from Zaire. International Journal Pharmacognosy, 32, 337-345. https://doi.org/10.3109/13880209409083012