A simple condensation
afforded some new
3-thioxo-1,2,4-triazin-5-one derivatives (4, 6 and 8).
Utilizing a facile condensation of (E)-4-(4’-bromo styryl)-2-oxo-3-buteneoic acid with thiosemicarbazide, dithioic formic acid hydrazide,
and thiocarbahydrazide in different conditions. Structures of these compounds
were confirmed by elemental and spectral analysis. The preliminary biocidal
activity of these products were evaluated against some microbial and compared
to Mycostatine and piperacillin as antibiotics were most of derivatives
exhibited good activity.
References
[1]
Eicher, T., Hauptmann, S. and Speicher, A. (2013) The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications. John Wiley & Sons.
[2]
Gautam, N., Ajmera, N., Gupta, S. and Gautam, D.C. (2012) Synthesis, Spectral Characterization and Biological Evaluation of 4H-1,4-Benzothiazines, Their Sulfones and Ribofuranosides. European Journal of Chemistry, 3, 106-111. https://doi.org/10.5155/eurjchem.3.1.106-111.489
[3]
Pandey, V.K., Yadav, S., Joshi, M.N. and Bajpai, S.K. (2000) Antiviral Activity of s-Triazines. Biological Memoirs, 26, 48-51.
[4]
Bishnoi, A. and Saxena, R. (2001) Synthesis of Hexahydro-1, 3, 5-Tri (8-Aryl-Aminomethyl-7-Hydroxy-4-Methyl-Quinolinyl)-s-Triazines as Possible Antiviral Agents. Indian Journal of Heterocyclic Chemistry, 11, 47-50.
[5]
Krauth, F., Dahse, H.M., Rüttinger, H.H. and Frohberg, P. (2010) Synthesis and Characterization of Novel 1,2,4-Triazine Derivatives with Antiproliferative Activity. Bioorganic & Medicinal Chemistry, 18, 1816-1821. https://doi.org/10.1016/j.bmc.2010.01.053
[6]
Abdel-Rahman, R.M., Makki, M.S.T. and Al-Romaizan, A.N. (2014) Synthesis of Novel Fluorine Substituted Isolated and Fused Heterobicyclic Nitrogen 1, 2, 4-Triazin-5-One Moiety as Potential Inhibitor towards HIV-1 Activity. 247-268.
[7]
Abdel-Rahman, R.M. (2001) Role of Uncondensed 1, 2, 4-Triazine Compounds and Related Heterobicyclic Systems as Therapeutic Agents—A Review. Pharmazie, 56, 18.
[8]
Makki, M.S.I., Abdel-Rahman, R.M. and Khan, K.A. (2014) Fluorine Substituted 1, 2, 4-Triazinones as Potential Anti-HIV-1 and CDK2 Inhibitors. Journal of Chemistry. https://doi.org/10.1155/2014/430573
[9]
Makki, M.S.T., Rahman, R.M.A. and Ali, O.A.A. (2016) Synthetic Approach for Novel Fluorine Substituted Thiadiazaphosphole Fused 1, 2, 4-Triazinopyridiazine Moieties as Bactericidal Agents. Asian Journal of Chemistry, 28, 917. https://doi.org/10.14233/ajchem.2016.19555
[10]
Kumar, A., Mukerjee, S.K. and Bhattacharya, S.K. (1983) Synthesis of N3-4-Substituted-aryl-N1-(alkyl/aryl-Substituted Aryl) Triazene-N1-Oxides as Potential Anticonvulsant Agents. Pharmazie, 38, 66.
[11]
Katsoulas, A., Rachid, Z., Brahimi, F., McNamee, J. and Jean-Claude, B.J. (2005) Engineering 3-Alkyltriazenes to Block bcr-abl Kinase: A Novel Strategy for the Therapy of Advanced bcr-abl Expressing Leukemias. Leukemia Research, 29, 693-700. https://doi.org/10.1016/j.leukres.2004.11.012
[12]
TawfekMakki, M.S., Rahman, R.A. and AbuAli, O.A. (2015) Synthesis of Some More New Fluorinated 1, 2, 4-triazino [3, 4-b][1, 3, 4] Thiadiazolonesand Their Molluscicidal Against Selective Snails-Part I. Journal of Chemistry, 9, 162-175.
[13]
Asiri, A.M., Baghlaf, A.O., Abdel-Rahman, R.M., Khan, S.A. and Ishaq, M. (2013) Synthesis and Spectroscopic Studies of Ru (II) Complexes of 1, 2, 4-Triazoles, 1, 2, 4-Triazines and Pyrimidine Derivatives. Asian Journal of Chemistry, 25, 7779. https://doi.org/10.14233/ajchem.2013.14604
[14]
Abdel-Rahman, R.M. (2000) Chemistry of Uncondensed 1,2,4-Triazines: Part Ii-Sulfur Containing 5-Oxo-1,2,4-Triazin-3-Yl Moiety: An Overview. Phosphorus, Sulfur, and Silicon and the Related Elements, 166, 315-357. https://doi.org/10.1080/10426500008076552
[15]
Cascioferro, S., Parrino, B., Spanò, V., Carbone, A., Montalbano, A., Barraja, P., Diana, P. and Cirrincione, G. (2017) An Overview on the Recent Developments of 1,2,4-Triazine Derivatives as Anticancer Compounds. European Journal of Medicinal Chemistry, 142, 328-375. https://doi.org/10.1016/j.ejmech.2017.08.009
[16]
Abdel-Rahman, M., R., ST Makki, M., E Ali, T., and A Ibrahim, M. (2013) 1,2,4-Triazine Chemistry Part III: Synthetic Strategies to Functionalized Bridgehead Nitrogen Heteroannulated 1,2,4-Triazine Systems and Their Regiospecific and Pharmacological Properties. Current Organic Chemistry, 10, 136-160.
[17]
Zaher, H.A., Jahine, H., Sherif, O. and Mohammady, R. (1979) Uncondensed 1,2,4-Triazines. 1. Behavior of 3-Hydrazino-5,6-Diphenyl-1,2,4-Triazine towards Acylating Agents, Activated Alkenes and Carbonyl-Compounds. Indian Journal of Chemistry—Section B, 18, 316-319.
[18]
Makki, M.S.T., Al-Romaizan, A.N. and Abdel-Rahman, R.M. (2010) Synthesis of Some More New Sulfur Compounds Bearing Heterocyclic Systems as Biocidal Agents-Part Ⅰ: Synthetic of 2-Thioxo Thiadiazinone Derivatives. Journal of Chemistry and Chemical Engineering, 4, 41-49.
[19]
Zamani, H.A., Rajabzadeh, G., Ganjali, M.R. and Norouzi, P. (2007) Determination of Gadolinium (III) Ions in Soil and Sediment Samples by a Novel Gadolinium Membrane Sensor Based on 6-methyl-4-{[1-(2-thienyl) methylidene] amino} 3-thioxo-3,4-dihydro-1,2,4-triazin-5-(2H)-one. Analytica Chimica Acta, 598, 51-57. https://doi.org/10.1016/j.aca.2007.07.028
[20]
Barry, A.L. (1980) Susceptibility Testing: Diffusion Test Procedures, Manual of Clinical Microbiology. American Society for Microbiology, Washington DC.
