Synthesis and antimicrobial activity of thiosemicarbazides, s-triazoles and their Mannich bases bearing 3-chlorophenyl moiety

European Journal of Medicinal Chemistry

Volumn 46, Issue 1, 2011, Pages 241-248

  Plech, Tomasz ^a   Wujec, Monika ^a   Siwek, Agata ^a   Kosikowska, Urszula ^a   Malm, Anna ^a  

^a MEDICAL UNIVERSITY OF LUBLIN   (Poland)

Author keywords

Mannich bases; Minimal bactericidal concentration (MBC); Minimal inhibitory concentration (MIC); s Triazoles

Indexed keywords

1 [(3 CHLOROPHENYL)CARBONYL] 4 (2 IODOPHENYL)THIOSEMICARBAZIDE; 1 [(3 CHLOROPHENYL)CARBONYL] 4 (2,5 DIFLUOROPHENYL)THIOSEMICARBAZIDE; 1 [(3 CHLOROPHENYL)CARBONYL] 4 (2,6 DIFLUOROPHENYL)THIOSEMICARBAZIDE; 1 [(3 CHLOROPHENYL)CARBONYL] 4 (4 FLUOROPHENYL)THIOSEMICARBAZIDE; 1 [(3 CHLOROPHENYL)CARBONYL] 4 (4 IODOPHENYL)THIOSEMICARBAZIDE; 1 [(3 CHLOROPHENYL)CARBONYL] 4 (4 METHOXYPHENYL)THIOSEMICARBAZIDE; 1 [(3 CHLOROPHENYL)CARBONYL] 4 (4 METHYLPHENYL)THIOSEMICARBAZIDE; 1 [(3 CHLOROPHENYL)CARBONYL] 4 PHENYLTHIOSEMICARBAZIDE; 1,2,4 TRIAZOLE DERIVATIVE; 4 (2 BROMOPHENYL) 1 [(3 CHLOROPHENYL)CARBONYL]THIOSEMICARBAZIDE; 4 (2 BROMOPHENYL) 5 (3 CHLOROPHENYL) 2,4 DIHYDRO 3H 1,2,4 TRIAZOLE 3 THIONE; 4 (4 BROMOPHENYL) 1 [(3 CHLOROPHENYL)CARBONYL]THIOSEMICARBAZIDE; 4 (4 BROMOPHENYL) 5 (3 CHLOROPHENYL) 2,4 DIHYDRO 3H 1,2,4 TRIAZOLE 3 THIONE; 4 (4 CHLOROPHENYL) 1 [(3 CHLOROPHENYL)CARBONYL]THIOSEMICARBAZIDE; 5 (3 CHLOROPHENYL) 4 (2 IODOPHENYL) 2,4 DIHYDRO 3H 1,2,4 TRIAZOLE 3 THIONE; 5 (3 CHLOROPHENYL) 4 (2,5 DIFLUOROPHENYL) 2,4 DIHYDRO 3H 1,2,4 TRIAZOLE 3 THIONE; 5 (3 CHLOROPHENYL) 4 (2,6 DIFLUOROPHENYL) 2,4 DIHYDRO 3H 1,2,4 TRIAZOLE 3 THIONE; 5 (3 CHLOROPHENYL) 4 (4 CHLOROPHENYL) 2,4 DIHYDRO 3H 1,2,4 TRIAZOLE 3 THIONE; 5 (3 CHLOROPHENYL) 4 (4 IODOPHENYL) 2,4 DIHYDRO 3H 1,2,4 TRIAZOLE 3 THIONE; 5 (3 CHLOROPHENYL) 4 (4 METHOXYPHENYL) 2 (PYRROLIDIN 1 YLMETHYL) 2,4 DIHYDRO 3H 1,2,4 TRIAZOLE 3 THIONE; 5 (3 CHLOROPHENYL) 4 (4 METHOXYPHENYL) 2,4 DIHYDRO 3H 1,2,4 TRIAZOLE 3 THIONE; 5 (3 CHLOROPHENYL) 4 (4 METHYLPHENYL) 2 (PYRROLIDIN 1 YLMETHYL) 2,4 DIHYDRO 3H 1,2,4 TRIAZOLE 3 THIONE; 5 (3 CHLOROPHENYL) 4 (4 METHYLPHENYL) 2,4 DIHYDRO 3H 1,2,4 TRIAZOLE 3 THIONE; 5 (3 CHLOROPHENYL) 4 PHENYL 2 (PYRROLIDIN 1 YLMETHYL) 2,4 DIHYDRO 3H 1,2,4 TRIAZOLE 3 THIONE; 5 (3 CHLOROPHENYL) 4 PHENYL 2,4 DIHYDRO 3H 1,2,4 TRIAZOLE 3 THIONE; AMPICILLIN; ANTIINFECTIVE AGENT; MANNICH BASE; THIOSEMICARBAZIDE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYCLIZATION; DRUG SCREENING; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; BACTERIA; HUMANS; MANNICH BASES; MICROBIAL SENSITIVITY TESTS; SEMICARBAZIDES; TRIAZOLES;

EID: 78650509744     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.11.010     Document Type: Article

References (28)

1. U. Salgn-Göken, N. Gökhan-Keleki, Ö Gökta, Y. Köysal, E. Kl, Ik, G. Aktay, and M. Özalp 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: synthesis, analgesic-anti-inflammatory and antimicrobial activities Bioorg. Med. Chem. 15 2007 5738 5751
2. S. Tehranchian, T. Akbarzadeh, M.R. Fazeli, H. Jamalifar, and A. Shafiee Synthesis and antibacterial activity of 1-[1,2,4-triazol-3-yl] and 1-[1,3,4-thiadiazol-2-yl]-3-methylthio-6,7-dihydro-benzo[c]thiophen-4(5H)-ones Bioorg. Med. Chem. Lett. 15 2005 1023 1025 (Pubitemid 40458642)
3. G. Turan-Zitouni, Z.A. Kaplanckl, M.T. Yldz, P. Chevallet, and D. Kaya Synthesis and antimicrobial activity of 4-phenyl/cyclohexyl-5-(1-phenoxyethyl)- 3-[N-(2-thiazolyl)acetamido]-thio-4H-1,24-triazole derivatives Eur. J. Med. Chem. 40 2005 607 613
4. H.M. Abdel-Rahman, and M.A. Hussein Synthesis of β-hydroxypropanoic acid derivatives as potential anti-inflammatory, analgesic and antimicrobial agents Arch. Pharm. Chem. Life Sci. 339 2006 378 387
5. A. Shafiee, A. Sayadi, M.H. Roozbahani, A. Foroumadi, and F. Kamal Synthesis and in vitro antimicrobial evaluation of 5-(1-methyl-5-nitro-2- imidazolyl)-4H-1,2,4-triazoles, Arch. Pharm. Pharm Med. Chem. 10 2002 495 499
6. H. Kitani, T. Kuroda, A. Moriguchi, H. Ao, F. Hirayama, Y. Ikeda, and T. Kawakita Synthesis and structural optimization of 7-(3,3-disubstituted-1- pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3- quinolinecarboxylic acids as antibacterial agents Bioorg. Med. Chem. Lett. 7 1997 515 520
7. Y. Tang, K.-X. Chen, H.-L. Jiang, and R.-Y. Ji QSAR/QSTR of fluoroquinolones: an example of simultaneous analysis of multiple biological activities using neural network method Eur. J. Med. Chem. 33 1998 647 658
8. H. Bayrak, H. Demirbas, S.A. Karaoglu, and N. Demirbas Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities Eur. J. Med. Chem. 44 2009 1057 1066
9. M. Ashok, B.M. Holla, and B. Poojary Convenient one pot synthesis and antimicrobial evaluation of some new Mannich bases carrying 4-methylthiobenzyl moiety Eur. J. Med. Chem. 42 2007 1095 1101
10. M.S. Karthikeyan, D.J. Prasad, B. Poojary, K.S. Bhat, B.M. Holla, and N.S. Kumari Synthesis and biological activity of Schiff and Mannich bases bearing 2,4-dichloro-5-fluorophenyl moiety Bioorg. Med. Chem. 14 2006 7482 7489
11. J.M. Domagala Structure-activity and structure-side-effect relationships for the quinolone antibacterials J. Antimicrob. Chemother. 33 1994 685 706
12. M. Dobosz, and A. Pachuta-Stec Synthesis of new thiourea derivatives of 1,2,4-triazoline-5-thione and 1,3,4-thiadiazole Acta Polon. Pharm. 51 1994 457 465
13. 2-1,2,4-triazoline-5-thiones Centr. Eur. J. Chem. 6 2008 47 53
14. H.N. Dogan, S. Rollas, and H. Erdeniz Synthesis, structure elucidation and antimicrobial activity of some 3-hydroxy-2-naphtoic acid hydrazide derivatives Il Farmaco 53 1998 462 467
15. N. Demirbas, S.A. Karaoglu, A. Demirbas, and K. Sancak Synthesis and antimicrobial activities of some new 1-(5-phenylamino-[1,3,4]thiadiazol-2-yl) methyl-5-oxo-[1,2,4]triazole and 1-(4-phenyl-5-thioxo-[1,2,4]triazol-3-yl) methyl-5-oxo-[1,2,4]triazole derivatives Eur. J. Med. Chem. 39 2004 793 804
16. A. Demirbas, D. Sahin, N. Demirbas, and S.A. Karaoglu Synthesis of some new 1,3,4-thiadiazol-2-ylmethyl-1,2,4-triazole derivatives and investigation of their antimicrobial activities Eur. J. Med. Chem. 44 2009 2896 2903
17. H. Bayrak, A. Demirbas, S.A. Karaoglu, and N. Demirbas Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities Eur. J. Med. Chem. 44 2009 1057 1066
18. M. Wujec, U. Kosikowska, A. Siwek, and A. Malm New derivatives of thiosemicarbazide and 1,2,4-triazoline-5-thione with potential antimicrobial activity Phosphorus Sulfur Silicon Relat. Elem. 184 2009 559 567
19. M. Wujec, U. Kosikowska, P. Paneth, and A. Malm Reaction of hydrazide of (tetrazol-5-yl)acetic acid with isothiocyanates and antimicrobial investigations of newly-obtained compounds Heterocycles 71 2007 2617 2626
20. A. Siwek, M. Wujec, M. Dobosz, and P. Paneth Synthesis and theoretical characterization of some new 4-substituted-1,3-diphenyl-5-thioxo-4,5-dihydro-1H- 1,2,4-triazoles with potential pharmacological activity Heteroatom Chem. 19 2008 713 718
21. I. Bourgeois, M. Pestel-Caron, J.F. Lemeland, J.L. Pons, and F. Caron Tolerance to the glycopeptides vancomycin and teicoplanin in coagulase-negative Staphylococci Antimicrob. Agents Chemother. 51 2007 740 743
22. E.L. White, W.J. Suling, L.J. Ross, L.E. Seitz, and R.C. Reynolds 2-Alkoxycarbonylaminopyridines: inhibitors of Mycobacterium tuberculosis FtsZ J. Antimicrob. Chemother. 50 2002 111 114
23. M.F.S. Lopes, T. Ribeiro, M. Abrantes, J.J.F. Marques, R. Tenreiro, and M.T.B. Crespo Antimicrobial resistance profiles of dairy and clinical isolates and type strains of enterococci Int. J. Food Microbiol. 103 2005 191 198
24. L. Nie, Z. Lie, J. Han, X. Zhang, R. Yang, W.-X. Liu, F.-Y. Wu, J.-W. Xie, Y.-F. Zhao, and Y.-B. Jiang Development of N-benzamidothioureas as a new generation of thiourea-based receptors for anion recognition and sensing J. Org. Chem. 69 2004 6449 6454
25. J.-P. Li, Q.-F. Luo, Y.-L. Wang, and H. Wang An efficient solid-state method for the preparation of acylthiosemicarbazides Synth. Commun. 31 2001 1793 1797
26. M.H. Shah, V.M. Patki, and M.Y. Mhasalkar 1,2,4-Triazole derivatives as possible diuretic agents J. Sci. Ind. Res. 21C 1962 76 78
27. CLSI Performance Standards for Antimicrobial Susceptibility Testing; Eighteenth International Supplement. CLSI Document M7-MIC 2008 Clinical Laboratory Standards Institute Wayne, PA
28. HyperChem 8.0.3 2007 HyperCube Inc. Gainsville, FL