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Design, Synthesis and Pharmacological Screening of β-Amino-, Thiadiazole/Thiadiazine-Phosphonate Based Triazole Motifs as Antimicrobial/Cytotoxic Agents


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1. W. E. Dismukes, Antifungal therapy: Lessons learned over the past 27 years, Clin. Infect. Dis. 42 (2006) 1289-1296; DOI: 10.1086/503043.10.1086/503043Search in Google Scholar

2. R. A. Smith, V. Cokkinides and O. W. Brawley, Cancer screening in the United States, a review of current American Cancer Society guidelines and issues in cancer screening, Cancer J. Clin. 59 (2009) 27-41; DOI: 10.3322/caac.20008.10.3322/caac.20008Search in Google Scholar

3. J. B. Bremner, J. I. Ambrus and S. Samosorn, Dual action-based approaches to antibacterial agents, Curr. Med. Chem. 14 (2007) 1459-1477; DOI: 10.2174/092986707780831168.10.2174/092986707780831168Search in Google Scholar

4. C. Hubschwerlen, J. L. Specklin, C. Sigwalt, S. Schroeder and H. H. Locher, Design, synthesis and biological evaluation of oxazolidinone-quinolone hybrids, Bioorg. Med. Chem. 11 (2003) 2313-2319; DOI: 10.1016/S0968-0896(03)00083-X.10.1016/S0968-0896(03)00083-XSearch in Google Scholar

5. A. K. Jordao, V. F. Ferreira, E. S. Lima, M. C. de Souza, E. C. Carlos, H. C. Castro, R. B. Geraldo, C. R. Rodrigues, M. C. Almeida and A. C. Cunha, Synthesis, antiplatelet and in silico evaluations of novel N-substituted- phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides, Bioorg. Med. Chem. 17 (2009) 3713-3719; DOI: 10.1016/j.bmc.2009.03.053.10.1016/j.bmc.2009.03.05319380229Search in Google Scholar

6. V. Calderone, I. Giorgi, O. Livi, E. Martinotti, E. Mantuano, A. Martelli and A. Nardi, Benzoyl and/ or benzyl substituted 1,2,3-triazoles as potassium channel activators, VIII, Eur. J. Med. Chem. 40 (2005) 521-528; DOI: 10.1016/ j.ejmech.2005.01.010.10.1016/j.ejmech.2005.01.01015922836Search in Google Scholar

7. R. F. Pratt, Inhibition of class A beta-lactamase by a specific phosphonate monoester, Science 246 (1989) 917-919; DOI: 10.1126/science.2814513.10.1126/science.28145132814513Search in Google Scholar

8. P. Duncanson, Y. K. Cheong, M. Motevalli and D. V. Griffiths, Novel approach to isoindolo[2,1-a] indol-6-ones, Org. Biomol. Chem. 10 (2012) 4266-4279; DOI: 10.1039/C2OB25314C.10.1039/c2ob25314c22526377Search in Google Scholar

9. S. Crotty, D. Maag, J. J. Arnold, W. Zhong, J. Y. N. Lau, Z. Hong, R. Andino and C. E. Cameron, The broad spectrum antiviral ribonucleotide, ribavirin, is an RNA virus mutagen, Nature Med. 6 (2000) 1375-1379; DOI: 10.1038/82191.10.1038/8219111100123Search in Google Scholar

10. N. Mauras, K. Bishop, D. Merinbaum, U. Emeribe, F. Agbo and E. Lowe, Pharmacokinetics and pharmacodynamics of anastrozole in pubertal boys with recent-onset gynecomastia, J. Clin. Endocrinol. Metab. 94 (2009) 2975-2978; DOI: 10.1210/jc.2008-2527.10.1210/jc.2008-252719470631Search in Google Scholar

11. W. M. Abdou, M. D. Khidre and R. E. Khidre, Application of phosphonyl carbanions to highly regioselective synthesis of some diazaphospholes and pyrazolinyl phosphonates, Eur. J. Med. Chem. 44 (2009) 526-532; DOI: 10.1016/j. ejmech.2008.03.032.Search in Google Scholar

12. W. M. Abdou, N. A. Ganoub and E. Sabry, Synthesis of antimicrobial N-phthaloyl-alanyl-derived amidophosphates and triazoles, Z. Naturforsch. 46b (2009) 1057-1064.10.1515/znb-2009-0911Search in Google Scholar

13. W. M. Abdou, A. A. Sediek and M. D. Khidre, An efficient method for the synthesis of spiro and fused N-heterocyclic phosphor esters. Reactions of triketoindan-2-oxime with a-phosphonyl carbanions, Monatsh. Chem. 139 (2008) 617-623; DOI: 10.1007/s00706-007-0806-z.10.1007/s00706-007-0806-zSearch in Google Scholar

14. W. M. Abdou, R. F. Barghash and A. A. Sediek, Design of new arylamino-2-ethane-1,1-diyl- and benzoxazole-2-methylene-bisphosphonates vs cytotoxicity and chronic inflammation diseases. From hydrophobicity prediction to synthesis and biological evaluation, Eur. J. Med. Chem. 57 (2012) 362-372; DOI: 10.1016/j. ejmech.2012.09.032.Search in Google Scholar

15. W. M. Abdou, R. F. Barghash and M. S. Bekheit, Carbodiimides in the synthesis of enamino- and a-aminophosphonates as peptidomimetics of analgesic/antiinflam-matory and anticancer agents, Arch. Pharm. Chem. Life Sci. 345 (2012) 884-895; DOI: 10.1002/ardp.201200142.10.1002/ardp.20120014222930562Search in Google Scholar

16. A. A. Kamel, A. Geronikaki and W. M. Abdou, Inhibitory effect of novel S,N-bisphosphonates on some carcinoma cell lines, osteoarthritis and chronic inflammation, Eur. J. Med. Chem. 51 (2012) 239-249; DOI: 10.1016/j.ejmech. 2012.02.047.Search in Google Scholar

17. C. H. Da Silva, V. B. Da Silva, J. Resende, P. F. Rodrigues, F. C. Bononi, C. G. Benevenuto and C. A. Taft, Computer-aided drug design and ADMET predictions for identification and evaluation of novel potential farnesyl- transferase inhibitors in cancer therapy, J. Mol. Graph. Model. 28 (2010) 513-523; DOI: 10.1016/j. jmgm.2009.11.011.Search in Google Scholar

18. A. A. Lagunin, O. A. Gomazkov, D. A. Filimonov, T. A. Gureeva, E. A. Dilakyan, E. V. Kugaevskaya, Y. E. Elisseeva, N. I. Solovyeva and V. V. Poroikov, Computer-aided selection of potential antihypertensive compounds with dual mechanism of action, J. Med. Chem. 46 (2003) 3326-3332; DOI: 10.1021/jm021089h.10.1021/jm021089h12852763Search in Google Scholar

19. Y. Bai, G. Zhao, C. Li, S. Zhao and Z. Shi, Microwave-enhanced reactions of 4-amino-5-mercapto-1,2,4-triazoles with benzoyl chloride and aromatic aldehydes, Synth. Commun. 38 (2008) 3311-3319; DOI: 10.1080/00397910802136649.10.1080/00397910802136649Search in Google Scholar

20. N. Al-Awadi, Y. Ibrahim, K. Kaul and H. Dib, Gas-phase elimination reactions of 4-arylideneimino-1,2,4-triazol-3(2H)-ones and their 3(2H)-thione analogues, J. Phys. Org. Chem. 14 (2001) 521-525; DOI: 10.1002/poc.383.10.1002/poc.383Search in Google Scholar

21. C. Perez, M. Pauli and P. Bazerque, An antibiotic assay by the agar well diffusion method, Acta Biol. Med. Exp. 15 (1990) 113-115. Search in Google Scholar

22. A. C. Scott, Laboratory Control of Antimicrobial Therapy, in Mackie and McCartney Practical Medical Microbiology (Eds. J. G. College, J. P. Duguid, A. G. Fraserand and B. P. Marmion), 13th ed., Churchill Livingstone, London 1989, pp. 161-181.Search in Google Scholar

23. Clinical and Laboratory Standards Institute (CLSI), Performance Standards for Antimicrobial Susceptibility Testing, 17th informational supplement, CLSI document M100-S17, Wayne (PEN) 2007.Search in Google Scholar

24. T. Kitamura, M. Itoh, T. Noda, M. Matsuura and K. Wakabayashi, Combined effects of cyclooxygenase-1 and cyclooxygenase-2 selective inhibitors on intestinal tumorigenesis in adenomatous polyposis coli gene knockout mice, Int. J. Cancer 109 (2004) 576-580; DOI: 10.1002/ijc.20012.10.1002/ijc.2001214991580Search in Google Scholar

25. M. R. Boyd and K. D. Paull, Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen, Drug Dev. Res. 34 (1995) 91-109; DOI: 10.1002/ ddr.430340203.10.1002/ddr.430340203Search in Google Scholar

26. J. March, Advanced Organic Chemistry, Reactions, Mechanisms, and Structures, 3rd ed., Wiley, New York 1985, pp. 82-140.Search in Google Scholar

27. J. Vinsová, K. Cermáková, A. Tomecková, M. Cecková, J. Jampílek, P. Cermák, J. Kunes, M. Dolezal and F. Staud, Synthesis and antimicrobial evaluation of new 2-substituted 5,7-di-tert-butylbenzoxazoles, Bioorg. Med. Chem. 14 (2006) 5850-5865; DOI: 10.1016/j.bmc.2006.05.030.10.1016/j.bmc.2006.05.03016784871Search in Google Scholar

28. E. S. T. Ali, Synthesis and antibacterial activity of some new thiadiaza/triaza-phospholes, thiadiaza/ triaza/tetraazaphosphinines and thiadiaza/tetraza-phosphepines containing 1,2,4-triazinone moiety, Eur. J. Med. Chem. 44 (2009) 4539-4546; DOI: 10.1016/j.ejmech.2009.06.022.10.1016/j.ejmech.2009.06.02219615792Search in Google Scholar

29. H. Lee and R. G. Harvey, 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in acetic acid, a convenient new reagent for the synthesis of aryl ketones and aldehydes via benzylic oxidation, J. Org. Chem. 53 (1988) 4587-4589; DOI: 10.1021/jo00254a035. 10.1021/jo00254a035Search in Google Scholar

eISSN:
1846-9558
Language:
English
Publication timeframe:
4 times per year
Journal Subjects:
Pharmacy, other