Synthesis of New Fluorine/Phosphorus Substituted 6-(2’-Amino Phenyl)-3-Thioxo-1,2,4-Triazin-5(2H, 4H)One and Their Related Alkylated Systems as Molluscicidal Agent as against the Snails Responsible for Bilharziasis Diseases
Affiliation(s)
Department of Chemistry, Faculty of Science, King Abdul Aziz University, Jeddah, KSA.
Department of Chemistry, Faculty of Science, King Abdul Aziz University, Jeddah, KSA.
ABSTRACT
New fluorine substituted 6-(5’-fluoro-2’-triphenylphosphiniminophenyl) 3-thioxo-1,2,4-triazin-5 (2H, 4H) one (2) was obtained via Wittig’s reaction of the corresponding 6-(5’-fluoro-2’-amino-phenyl)-3-thioxo-1,2,4-triazinone (1). Behavior of compound 2 towards alkylating agents and/or oxidizing agents was studied were, N-hydroxyl (3), Mannich base (4,5), S-alkyl (6,7,8) and thiazolo [3,2-b][1,2,4] triazinones (10-14) and or 3-disulfide (18), 3-sulfonic acid 19 and 1,2,4-triazin-3,5-Dionne (20) derivatives obtained. Structures of the new products are established by elemental and spectral data. The new targets obtained screened as Molluscicidalagents against Biomophlaria Alexandrina snails responsible for Bilharziasis diseases, in compare with Baylucide as standard drug.
New fluorine substituted 6-(5’-fluoro-2’-triphenylphosphiniminophenyl) 3-thioxo-1,2,4-triazin-5 (2H, 4H) one (2) was obtained via Wittig’s reaction of the corresponding 6-(5’-fluoro-2’-amino-phenyl)-3-thioxo-1,2,4-triazinone (1). Behavior of compound 2 towards alkylating agents and/or oxidizing agents was studied were, N-hydroxyl (3), Mannich base (4,5), S-alkyl (6,7,8) and thiazolo [3,2-b][1,2,4] triazinones (10-14) and or 3-disulfide (18), 3-sulfonic acid 19 and 1,2,4-triazin-3,5-Dionne (20) derivatives obtained. Structures of the new products are established by elemental and spectral data. The new targets obtained screened as Molluscicidalagents against Biomophlaria Alexandrina snails responsible for Bilharziasis diseases, in compare with Baylucide as standard drug.
KEYWORDS
Fluorine, Phosphorus, Sulfur-1, 2, 4-Triazine, Characteristic Properties, Molluscicidal Activity
Fluorine, Phosphorus, Sulfur-1, 2, 4-Triazine, Characteristic Properties, Molluscicidal Activity
Cite this paper
Al-Romaizan, A. , Makki, M. and Abdel-Rahman, R. (2014) Synthesis of New Fluorine/Phosphorus Substituted 6-(2’-Amino Phenyl)-3-Thioxo-1,2,4-Triazin-5(2H, 4H)One and Their Related Alkylated Systems as Molluscicidal Agent as against the Snails Responsible for Bilharziasis Diseases. International Journal of Organic Chemistry, 4, 154-168. doi: 10.4236/ijoc.2014.42017.
Al-Romaizan, A. , Makki, M. and Abdel-Rahman, R. (2014) Synthesis of New Fluorine/Phosphorus Substituted 6-(2’-Amino Phenyl)-3-Thioxo-1,2,4-Triazin-5(2H, 4H)One and Their Related Alkylated Systems as Molluscicidal Agent as against the Snails Responsible for Bilharziasis Diseases. International Journal of Organic Chemistry, 4, 154-168. doi: 10.4236/ijoc.2014.42017.
References
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http://dx.doi.org/10.1016/j.tetasy.2005.10.038 [18] Ali, P., Pamakanth, P. and Meshram, J. (2010) Exploring Microwave Synthesis for Co-Ordination: Synthesis, Spectral Characterization and Comparative Study of Fluorine Substituted Transition Metal Complexes with Binuclear Core Derived from 4-Amino-2,3-Dimethyl-1-Phenyl-3-Pyrazolin-5-One. Journal of Coordination Chemistry, 63, 323-329.
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http://dx.doi.org/10.1080/10426500390228738 [23] Abdel-Rahman, R.M. and El-Mahdy, K. (2012) Biological Evaluation of Pyramidpyrimidines as Multi-Targeted Small Molecule Inhibitors and Resistance Modifying Agents. Heterocycles, 85, 2391-2414.
http://dx.doi.org/10.3987/REV-12-745 [24] Zaki, M.T., Abdel-Rahman, R.M. and El Sayed, A.Y. (1995) Use of Arylidenrhodanines for the Determination of Cu(II) Hg(II) and CN﹣. Analytica Chimica Acta, 307, 127-138.
http://dx.doi.org/10.1016/0003-2670(95)00048-5 [25] Slawinski, J. and Gdaniec, M. (2005) Synthesis, Molecular Structure, and in Vitro Antitumor Activity of New 4-Chlore-2-Mercaptobenzenesulfonamide Derivatives. European Journal of Medicinal Chemistry, 40, 377-389.
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http://dx.doi.org/10.1016/j.jfluchem.2006.10.019
[1] Abdel-Rahman, R.M. and Ali, T.E. (2013) Synthesis and Biological Evaluation of Some New Polyfluorinated 4- Thiazolidinone and α-Aminophosphonic Acid Derivatives. Monatshefte fur Chemie, 144, 1243-1252.
http://dx.doi.org/10.1007/s00706-013-0934-6 [2] Makki, M.S.T., Bakhotmah, D.A. and Abdel-Rahman, R.M. (2012) Highly Efficient Synthesis of Novel Fluorine Bearing Quinoline-4-Carboxylic Acid and the Related Compounds as Amylolytic Agents. International Journal of Organic Chemistry, 2, 49-55.
http://dx.doi.org/10.4236/ijoc.2012.21009 [3] Makki, M.S.T., Bakhotmah, D.A., Abdel-Rahman, R.M. and El-Shahawy, M.S. (2012) Designing and Synthesis of New Fluorine Substituted Pyrimidine-Thion-5-Carbonitrles and the Related Derivatives as Photochemical Probe Agent for Inhibition of Vitiligo Disease. International Journal of Organic Chemistry, 2, 311-320.
http://dx.doi.org/10.4236/ijoc.2012.223043 [4] Abdel-Rahman, R.M., Makki, M.S.T. and Bawazir, W.A. (2011) Synthesis of Some New Fluorine Heterocyclic Nitrogen Systems Derived from Sulfa Drugs as Photochemical Probe Agents for Inhibition of Vitiligo Disease Part I. E-Journal of Chemistry, 8, 405-414. [5] Abdel-Rahman, R.M., Makki, M.S.T. and Bawazir, W.A. (2010) Syntheisis of Fluorine Heterocyclic Nitrogen Systems Derived from Sulfa Drugs as Photochemical Probe Agents for Inhibition of Vitiligo Disease Part II. E-Journal of Chemistry, 7, 593-5102. [6] Abdel-Rahman, R.M. (2003) Synthesis of New Phosphaheterobicyclic Systems Containing 1,2,4-Triazine Moiety— Part IX: Straight forward Synthesis of New Fluorine Bearing 5-Phospha-1,2,4 Triazine/1,2,4-Triazepine-3-Thiones; Part X: Synthesis of New Phosphaheterobicyclic Systems, Containing a 1,2,4-Triazine Moiety. Trends in Heterocyclic Chemistry, 8, 187-195. [7] Ali, T.E., Abdel-Rahman, R.M., Hanafy, F.J. and El Edfawy, S.M. (2008) Synthesis and Molluscicidal Activity of Phosphorus—Containing Heterocyclic Compounds Derived from 5,6-Bis (4-brome phenyl)-3-hydrazino-1,2,4-triazine. Phosphorus, Sulfur, and Silicon, 183, 2565-2577. [8] Abdel-Rahman, R.M., Ibrahim, M.A. and Ali, T.E. (2010) 1,2,4-Triazine Chemistry Part II, Synthetic Approaches for Phosphorus Containing 1,2,4-Triazine Derivatives. European Journal of Chemistry, 1, 388-396.
http://dx.doi.org/10.5155/eurjchem.1.4.388-396.154 [9] Blakley, B., Brousseau, P., Fournier, M. and Voccia, I. (1999) Immunotoxicity of Pesticides. Toxicology Industrial Health, 15, 119-132.
http://dx.doi.org/10.1177/074823379901500110 [10] Sengupta, A.K., Bajaj, O.P. and Agarwal, K.C. (1980) Synthesis and Insecticide Activity of N4-Aryl-N1-(0.0-Dial-kylthiophosphoryl) Piperazines. Journal of the Indian Chemical Society, 57, 1170-1171. [11] Du, Y.M., Tian, J., Liao, H., Bai, C.J., Yan, X.L. and Liu, G.D. (2009) Aluminum Tolerance and High Phosphorus Efficiency Helps Stylosanthes Better Adapt to Low-P Acid Soils. Annals of Botony, 103, 1239-1247.
http://dx.doi.org/10.1093/aob/mcp074 [12] Abdel-Rahman, R.M. (2001) Role of Uncondensed 1,2,4-Triazine Derivatives as Biological Plant Protection Agents. Pharmazie, 56, 195-212. [13] Abdel-Rahman, R.M. (2001) Role of Uncondensed 1,2,4-Triazine Compounds and Related Heterobicyclic Systems as Therapeutic Agents. Pharmazie, 56, 18-30. [14] Abdel-Rahman, R.M. (1991) Synthesis and Anti Human Immune Virus Activity of Some New Fluorine Containing Substituted 3-Thixo-1,2-4-Triazin-5-Ones. Farmaco, 46, 379-389. [15] Abdel-Rahman, R.M. (1992) Synthesis of Some New Fluorine Bearing Tri-Substituted 3-Thioxo-1,2,4-Triazine-5-Ones as Potential Anti Cencer Agent. Farmaco, 47, 319-326. [16] Makki, M.S.T., Abdel-Rahman, R.M. and El-Shahawi, M.S. (2012) Synthesis and Voltammetric Study of Some New Macrocylis of Arsenic (III) in Wastewater and as Molluscicidal Agents against Biomophalaria Alexandrina Snails. Comptes Rendus Chimie, 15, 617-626. [17] Basavaiah, D., Chandrashekar, V., Das, U. and Reddy, G.J. (2005) A Study toward Understanding the Role of a Phosphorus Stereogenic Center in (5S)-1,3-Diaza-2-Phospha-2-oxo-3-Phenylbicyclo(3.3.0)Octane Derivatives as Catalysts in the Borane-Mediated Asymmetric Reduction of Prochiral Ketones. Tetrahedron: Asymmetry, 16, 3955-3962.
http://dx.doi.org/10.1016/j.tetasy.2005.10.038 [18] Ali, P., Pamakanth, P. and Meshram, J. (2010) Exploring Microwave Synthesis for Co-Ordination: Synthesis, Spectral Characterization and Comparative Study of Fluorine Substituted Transition Metal Complexes with Binuclear Core Derived from 4-Amino-2,3-Dimethyl-1-Phenyl-3-Pyrazolin-5-One. Journal of Coordination Chemistry, 63, 323-329.
http://dx.doi.org/10.1080/00958970903305437 [19] 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. Phosphorus, Sulfur and Silicon, 166, 315-357.
http://dx.doi.org/10.1080/10426500008076552 [20] Abdel-Rahman, R.M. and Islam, I.E. (1993) Synthesis and Reactions of Acetonitrile Derivatives Bearing a 5,6-Dipheny-1,2,4-Triazin-3-yl Moiety. Indian Journal of Chemistry, Section B, 32, 526-529. [21] Abdel-Rahman, R.M., Seada, M., Fawzy, M.M. and El-Baz, I. (1993) Synthesis and Anti-Canceranti Human Immune Virus Activities of Some New Thioether Bearing a 1,2,4-Triazine-3-Hydrazones. Farmaco, 48, 397-406. [22] EL-Gendy, Z., Morsy, J., Allimony, H.A., Abdel-Monem, W.R. and Abdel-Rahman, R.M. (2003) Synthesis of Heter-obicyclic Nitrogen System Bearing the 1,2,4-Triazine Moiety as Anti-HIV and Anti-Cancer Drugs, Part II. Phosphorus, Sulfur and Silicon, 178, 2055-2071.
http://dx.doi.org/10.1080/10426500390228738 [23] Abdel-Rahman, R.M. and El-Mahdy, K. (2012) Biological Evaluation of Pyramidpyrimidines as Multi-Targeted Small Molecule Inhibitors and Resistance Modifying Agents. Heterocycles, 85, 2391-2414.
http://dx.doi.org/10.3987/REV-12-745 [24] Zaki, M.T., Abdel-Rahman, R.M. and El Sayed, A.Y. (1995) Use of Arylidenrhodanines for the Determination of Cu(II) Hg(II) and CN﹣. Analytica Chimica Acta, 307, 127-138.
http://dx.doi.org/10.1016/0003-2670(95)00048-5 [25] Slawinski, J. and Gdaniec, M. (2005) Synthesis, Molecular Structure, and in Vitro Antitumor Activity of New 4-Chlore-2-Mercaptobenzenesulfonamide Derivatives. European Journal of Medicinal Chemistry, 40, 377-389.
http://dx.doi.org/10.1016/j.ejmech.2004.11.014 [26] Abdel-Rahman, R.M. and Abdel-Malik, N.S. (1990) Syn-thesis of Some New 3,6-Diheteroarryl-1,2,4-Triazine-5-Ones and Their Effect on Amylolytic Activity of Some Fungi. Pakistan Journal of Science and Industrial Research, 33, 142-147. [27] Ebraheem, M.A., Abdel-Rahman, R.M., Abdel-Haleem, A.M., Ibrahim, S.S. and Allimony, H.A. (2008) Synthesis and Antifungal Activity of Novel Polyheterocyclic Compound Containing Fused 1,2,4-Triazine Moiety. Arkivoc, 21, 202-213. [28] WHO (1953) Expert Committee on Bilharziasis, 65, 33. [29] WHO (1965) Snail Control Information of Bilharziasis Monograph Series. 50, 124. [30] Smarti, B.E. (2001) Fluorine Substituent Effect (on Bioactivity). Journal of Fluorine Chemistry, 109, 3-11.
http://dx.doi.org/10.1016/S0022-1139(01)00375-X [31] Billard, T., Gille, S., Ferry, A., Bartelemy, A., Christophe, C. and Langlois, B.R. (2005) From Fluoral to Heterocycles: A Survey of Polyfluorinated Iminiums Chemistry. Journal of Fluorine Chemistry, 126, 189-196.
http://dx.doi.org/10.1016/j.jfluchem.2004.08.007 [32] Isanbor, C. and O’Hagan, D. (2006) Fluorine in Medicinal Chemistry: A Review of Anti-Cancer Agents. Journal of Fluorine Chemistry, 127, 303-319.
http://dx.doi.org/10.1016/j.jfluchem.2006.01.011 [33] Sandford, G. (2007) Elemental Fluorine in Organic Chemistry (1997-2006). Journal of Fluorine Chemistry, 128, 90-104.
http://dx.doi.org/10.1016/j.jfluchem.2006.10.019