Synthesis and structure-activity relationship studies of 4-arylthiosemicarbazides as topoisomerase IV inhibitors with Gram-positive antibacterial activity. Search for molecular basis of antibacterial activity of thiosemicarbazides

European Journal of Medicinal Chemistry

Volumn 46, Issue 11, 2011, Pages 5717-5726

  Siwek, Agata ^a,b   Sta̧czek, Paweł ^c   Stefańska, Joanna ^d  

^a MEDICAL UNIVERSITY OF LUBLIN   (Poland)

^b LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

^c UNIVERSITY OF LODZ   (Poland)

^d MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

Antibacterial activity; Bacterial topoisomerase IV; Molecular docking; SAR; Thiosemicarbazide derivatives

Indexed keywords

1 (4 METHYL THIADIAZOL 5 CARBONYL) 4 (4 NITROPHENYL)THIOSEMICARBAZIDE; 1 (INDOL 2 CARBONYL) 4 (4 NITROPHENYL)THIOSEMICARBAZIDE; 4 (2 BROMOPHENYL) 1 (4 METHYL THIADIAZOL 5 YL)CARBONYLTHIOSEMICARBAZIDE; 4 (2 BROMOPHENYL) 1 (INDOL 2 YL)CARBONYLTHIOSEMICARBAZIDE; 4 (2 FLUOROPHENYL) 1 (INDOL 2 YL)CARBONYLTHIOSEMICARBAZIDE; 4 (2 TRIFLUOROMETHYLPHENYL) 1 (4 METHYL THIADIAZOL 5 YL)CARBONYLTHIOSEMICARBAZIDE; 4 (2,4 DICHLOROPHENYL) 1 (4 METHYL THIADIAZOL 5 YL)CARBONYLTHIOSEMICARBAZIDE; 4 (2,4 DIFLUOROPHENYL) 1 (4 METHYL THIADIAZOL 5 YL)CARBONYLTHIOSEMICARBAZIDE; 4 (2,4 DIFLUOROPHENYL) 1 (INDOL 2 YL)CARBONYLTHIOSEMICARBAZIDE; 4 (2,5 DIFLUOROPHENYL) 1 (4 METHYL THIADIAZOL 5 YL)CARBONYLTHIOSEMICARBAZIDE; 4 (3 FLUOROPHENYL) 1 (4 METHYL THIADIAZOL 5 YL)CARBONYLTHIOSEMICARBAZIDE; 4 (4 BROMOPHENYL) 1 (4 METHYL THIADIAZOL 5 YL)CARBONYLTHIOSEMICARBAZIDE; 4 (4 CHLOROPHENYL) 1 (4 METHYL THIADIAZOL 5 YL)CARBONYLTHIOSEMICARBAZIDE; 4 (4 FLUOROPHENYL) 1 (4 METHYL THIADIAZOL 5 YL)CARBONYLTHIOSEMICARBAZIDE; 4 (4 FLUOROPHENYL) 1 (INDOL 2 YL)CARBONYLTHIOSEMICARBAZIDE; 4 (4 METHOXYPHENYL) 1 (4 METHYL THIADIAZOL 5 YL)CARBONYLTHIOSEMICARBAZIDE; 4 (4 NITROPHENYL) 1 (PYRROL 2 YL)CARBONYLTHIOSEMICARBAZIDE; DNA TOPOISOMERASE (ATP HYDROLYSING); DNA TOPOISOMERASE IV; ISOMERASE INHIBITOR; THIOSEMICARBAZIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS CEREUS; BACILLUS SUBTILIS; BORDETELLA BRONCHISEPTICA; DRUG MECHANISM; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; ESCHERICHIA COLI; GRAM POSITIVE BACTERIUM; IC 50; INFRARED SPECTROSCOPY; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; MOLECULAR MODEL; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET RADIATION;

ANTI-BACTERIAL AGENTS; CHEMISTRY TECHNIQUES, SYNTHETIC; DNA TOPOISOMERASE IV; DRUG DISCOVERY; GRAM-POSITIVE BACTERIA; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SEMICARBAZIDES; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP; TOPOISOMERASE INHIBITORS;

EID: 80054913989     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.09.034     Document Type: Article

References (45)

1. S.B. Levy Multidrug resistance - a sign of the times N. Eng. J. Med. 338 1998 1376 1378
2. W. Witte Antibiotic resistance in gram-positive bacteria: epidemiological aspects J. Antimicrob. Chem. 44 1999 1 9 (Pubitemid 29425486)
3. R.F. Service Antibiotics that resist resistance Science 270 1995 724 727
4. J.A. Heinemann, R.G. Ankenbauer, and C.F. Amábile-Cuevas Do antibiotics maintain antibiotic resistance? Drug Discov. Today 5 2000 195 204 (Pubitemid 30211616)
5. T. Komine, A. Kojima, Y. Asahina, T. Saito, H. Takano, T. Shibue, and Y. Fukusa Synthesis and structure-activity relationship studies of highly potent novel oxazolidinone antibacterials J. Med. Chem. 51 2008 6558 6562
6. A.R. Renslo, G.W. Luehr, and M.F. Gordeev Recent developments in the identification of novel oxazolidinone antibacterial agents Bioorg. Med. Chem. 14 2006 4227 4240
7. D.J. Bast, and J.C.S. de Azavedo Quinolone resistance: older concepts and newer developments Curr. Infect. Dis. Rep. 3 2001 20 28
8. R.J. Kerns, M.J. Rybak, G.W. Kaatz, F. Vaka, R. Cha, R.G. Grucz, and V.U. Diwadkar Structural features of piperazinyl-linked ciprofloxacin dimmers required for activity against drug-resistant strains of Staphylococcus aureus Bioorg. Med. Chem. Lett. 13 2003 2109 2112 (Pubitemid 36694285)
9. M. Bukvić Krajačić, P. Novak, M. Dumić, M. Cindrić, H. Čipčić Paljetak, and N. Kujundžić Novel ureas and thioureas of 15-membered azalides with antibacterial activity against key respiratory pathogens Eur. J. Med. Chem. 44 2009 3459 3470
10. L. Xu, A.K. Farthing, J.F. Dropinski, P.T. Meinke, Ch. McCallum, P.S. Leavitt, E.J. Hickey, L. Colwell, J. Barrett, and K. Liu Nocathiacin analogs: synthesis and antibacterial activity of novel water-soluble amides Bioorg. Med. Chem. Lett. 19 2009 3531 3535
11. M.S. Kabir, K. Engelbrecht, R. Polanowski, S.M. Krueger, R. Ignasiak, M. Rott, W.R. Schwan, M.E. Stemper, K.D. Reed, D. Sherman, J.M. Cook, and A. Monte New classes of Gram-positive selective antibacterials: inhibitors of MRSA and surrogates of the causative agents of anthrax and tuberculosis Bioorg. Med. Chem. Lett. 18 2008 5745 5749
12. Y. Hirokawa, H. Kinoshita, T. Tanaka, T. Nakamura, K. Fujimoto, S. Kashimoto, T. Kojima, and S. Kato Pleuromutilin derivatives having a purine ring. Part 1: new compounds with promising antibacterial activity against resistant Gram-positive pathogens Bioorg. Med. Chem. Lett. 18 2008 3556 3561 (Pubitemid 351787564)
13. G. Aridoss, S. Amirthaganesan, N.A. Kumar, J.T. Kim, K.T. Lim, S. Kabilan, and Y.T. Jeong A facile synthesis, antibacterial, and antitubercular studies of some piperidin-4-one and tetrahydropyridine derivatives Bioorg. Med. Chem. Lett. 18 2008 6542 6548
14. B.J. Bradbury, and M.J. Pucci Recent advances in bacterial topoisomerase inhibitors Curr. Opin. Pharmacol. 8 2008 574 581 and references therein
15. D.A. Ostrov, J.A. Hernández Prada, P.E. Corsino, K.A. Finton, N. Le, and T.C. Rowe Discovery of novel DNA gyrase inhibitors by high-throughput virtual screening Antimicrob. Agents Chemother. 51 2007 3688 3698 (Pubitemid 47519360)
16. M. Oblak, S.G. Grdadolnik, M. Kotnik, R. Jerala, M. Filipič, and T. Šolmajer In silico fragment-based discovery of indolin-2-one analogues as potent DNA gyrase inhibitors Bioorg. Med. Chem. Lett. 15 2005 5207 5210 (Pubitemid 41463648)
17. M. Oblak, S. Golič Grdadolnik, M. Kotnik, A. Poterszman, R.A. Atkinson, H. Nierengarten, D. Desplancq, D. Moras, and T. Solmajer Biophysical characterization of an indolinone inhibitor in the ATP-binding site of DNA gyrase Biochem. Biophys. Res. Commun. 349 2006 1206 1213 (Pubitemid 44430194)
18. C. Ku, G. Ayhan-Klcgil, S. Özbey, F. Betül Kaynak, M. Kaya, T. oban, and B. Can-Eke DNA topoisomerases and their poisoning by anticancer and antibacterial drugs Chem. Biol. 17 2010 421 433
19. J.J. Champoux DNA topoisomerases: structure, function, and mechanism Annu. Rev. Biochem. 70 2001 369 413 (Pubitemid 32662215)
20. J.C. Wang Cellular roles of DNA topoisomerases: a molecular perspective Nat. Rev. Mol. Cell. Biol. 3 2002 430 440 (Pubitemid 34685700)
21. A.M. Wilstermann, and N. Osheroff Stabilization of eukaryotic topoisomerase II-DNA cleavage complexes Curr. Top. Med. Chem. 3 2003 321 338
22. C. Levine, H. Hiasa, and K.J. Marians DNA gyrase and topoisomerase IV: biochemical activities, physiological roles during chromosome replication, and drug sensitivities Biochem. Biophys. Acta 1400 1998 29 43 (Pubitemid 28475094)
23. A. Siwek, P. Sta̧czek, M. Wujec, J. Stefańska, U. Kosikowska, A. Malm, S. Jankowski, and P. Paneth Biological and docking studies of topoisomerase IV inhibition by thiosemicarbazides J. Mol. Model. 17 2011 2297 2303
24. I.R. Ezabadi, C. Camoutsis, P. Zoumpoulakis, A. Geronikaki, M. Soković, J. Glamoćilija, and A. Ćiri&cacute Sulfonamide-1,2,4-triazole derivatives as antifungal and antibacterial agents: synthesis biological evaluation, lipophilicity, and conformational studies Bioorg. Med. Chem. 16 2008 1150 1161 (Pubitemid 351193036)
25. C. Ku, G. Ayhan-Klcgil, S. Özbey, F.B. Kaynak, M. Kaya, T. oban, and B. Can-Eke Synthesis and antioxidant properties of novel N-methyl-1,3,4- thiadiazol-2-amine and 4-methyl-2H-1,2,4-triazole-3(4H)-thione derivatives of benzimidazole class Bioorg. Med. Chem. 16 2008 4294 4303 (Pubitemid 351539047)
26. T. Önkol, D.S. Doruer, L. Uzun, S. Adak, S. Özkan, and M.F.J. ahin J. Enzym. Inhib. Med. Chem. 23 2008 277 284
27. H.Z. Shams, R.M. Mohareb, M.H. Helal, and A.E. Mahmoud Phosphorus Sulfur 182 2007 237 263
28. F.E. Norrington, R.M. Hyde, S.G. Williams, and R. Wootton Physiochemical-activity relations in practice. 1. A rational and self-consistent data bank J. Med. Chem. 18 1975 604 607
29. A. Cammarata Quantitated structure-activity relationships Annu. Rep. Med. Chem. 6 1971 245 253
30. E. Kutter, and C. Hansch Steric parameters in drug design. Monoamine oxidase inhibitors and antihistamines J. Med. Chem. 12 1969 647 652
31. C. Oefner, A. Douangamath, A. D'Arcy, S. Häfeli, D. Mareque, A. Mac Sweeney, J. Padilla, S. Pierau, H. Schulz, M. Thormann, S. Wadman, and G.E. Dale The 1.15A crystal structure of the Staphylococcus aureus methionyl- aminopeptidase and complexes with triazole based inhibitors J. Mol. Biol. 332 2003 13 21 (Pubitemid 36999727)
32. T. Fujita, J. Iwasa, and C. Hansch A new substituent constant, π, derived from partition coefficients J. Am. Chem. Soc. 86 1964 5175 5180
33. C. Hansch, and W.J. Dunn Linear relationship between lipophilic character and biological activity of drugs J. Pharm. Sci. 61 1972 1 19
34. C. Hansch, and J.M. Clayton Lipophilic character and biological activity of drugs II: the parabolic case J. Pharm. Sci. 62 1973 1 21
35. A.E. Bird, and A.C. Marshall Correlation of serum binding of penicillins with partition coefficients Biochem. Pharmacol. 16 1967 2275 2290
36. A. Siwek, K. Świderek, S. Jankowski, Problems with molecular mechanics implementations on the example of 4-benzoyl-1-(4-methyl-imidazol-5-yl) -carbonylthiosemicarbazide, J. Mol. Model., online first doi: 10.1007/s00894-011-1117-1.
37. A. Siwek, M. Wujec, J. Stefańska, and P. Paneth Antimicrobial properties of 4-aryl-3-(2-methyl-furan-3-yl)-Δ2-1,2,4-triazoline-5-thiones Phosphorus Sulfur 184 2009 3149 3159
38. É.C. Moreno Nascimento, and J.B.L. Martins Electronic structure and PCA analysis of covalent and non-covalent acetylcholinesterase inhibitors J. Mol. Model. 17 2011 1371 1379
39. A. Siwek, M. Wujec, M. Dobosz, and I. Wawrzycka-Gorczyca Study of direction of cyclization of 1-azolil-4-aryl/alkyl-thiosemicarbazides Heteroatom. Chem. 21 2010 521 532
40. Clinical and Laboratory Standards Institute Performance Standards for Antimicrobial Disc Susceptibility Tests; Approved Standard M2-A9 2006 Clinical and Laboratory Standards Institute Wayne, PA, USA
41. Clinical and Laboratory Standards Institute Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically; Approved Standard M7-A7 2006 Clinical and Laboratory Standards Institute Wayne, PA, USA
42. Hyperchem 8.0.3 2007 HyperCube Inc. Gainsville, FL, USA
43. O. Trott, and A.J. Olson AutoDockVina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading J. Comput. Chem. 31 2010 455 461
44. www.pdb.org and the following citation: H.M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov, P.E. Bourne, The protein data bank, Nucleic Acids Res. 28 (2000) 235-242. (Pubitemid 30047768)
45. V. Lamour, L. Hoermann, J.M. Jeltsch, P. Oudet, and D. Moras An open conformation of the Thermus thermophilus gyrase B ATP-binding domain J. Biol. Chem. 277 2002 18947 18953 (Pubitemid 34952456)