Salicylanilide diethyl phosphates: Synthesis, antimicrobial activity and cytotoxicity

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 2, 2014, Pages 728-737

  Vinšová, Jarmila ^a   Kozic, Ján ^a   Krátký, Martin ^a   Stolaříková, Jiřina ^b   Mandíková, Jana ^a   Trejtnar, František ^a   Buchta, Vladimír ^a,c  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b Zdravotniho ustavu se sidlem v Ostrave   (Czech Republic)

^c CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Cytotoxicity; Diethyl phosphate; In vitro antimicrobial activity; In vitro antimycobacterial activity; Salicylanilide

Indexed keywords

2 [(3 BROMOPHENYL)CARBAMOYL] 4 CHLOROPHENYL DIETHYL PHOSPHATE; 2 [(3 BROMOPHENYL)CARBAMOYL] 5 CHLOROPHENYL DIETHYL PHOSPHATE; 2 [(4 BROMOPHENYL)CARBAMOYL] 4 CHLOROPHENYL DIETHYL PHOSPHATE; 2 [(4 BROMOPHENYL)CARBAMOYL] 5 CHLOROPHENYL DIETHYL PHOSPHATE; 4 BROMO 2 [(3 BROMOPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 4 BROMO 2 [(3 CHLOROPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 4 BROMO 2 [(3 FLUOROPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 4 BROMO 2 [(3,4 DICHLOROPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 4 BROMO 2 [(4 BROMOPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 4 BROMO 2 [(4 CHLOROPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 4 BROMO 2 [(4 FLUOROPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 4 BROMO 2 [[3 (TRIFLUOROMETHYL)PHENYL]CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 4 BROMO 2 [[4 (TRIFLUOROMETHYL)PHENYL]CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 4 CHLORO 2 [(3 CHLOROPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 4 CHLORO 2 [(3 FLUOROPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 4 CHLORO 2 [(3,4 DICHLOROPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 4 CHLORO 2 [(4 CHLOROPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 4 CHLORO 2 [(4 FLUOROPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 4 CHLORO 2 [[3 (TRIFLUOROMETHYL)PHENYL]CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 4 CHLORO 2 [[4 (TRIFLUOROMETHYL)PHENYL]CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 5 CHLORO 2 [(3 CHLOROPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 5 CHLORO 2 [(3 FLUOROPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 5 CHLORO 2 [(3,4 DICHLOROPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 5 CHLORO 2 [(4 CHLOROPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 5 CHLORO 2 [(4 FLUOROPHENYL)CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 5 CHLORO 2 [[3 (TRIFLUOROMETHYL)PHENYL]CARBAMOYL]PHENYL DIETHYL PHOSPHATE; 5 CHLORO 2 [[4 (TRIFLUOROMETHYL)PHENYL]CARBAMOYL]PHENYL DIETHYL PHOSPHATE; SALICYLANILIDE DERIVATIVE; SALICYLANILIDE DIETHYL PHOSPHATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; ORGANOPHOSPHATE;

ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; ASPERGILLUS FUMIGATUS; BACTERIAL STRAIN; BIOLOGICAL ACTIVITY; CANDIDA ALBICANS; CANDIDA KRUSEI; CELL STRAIN HEPG2; CONTROLLED STUDY; CYTOTOXICITY; DRUG EFFICACY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LICHTHEIMIA CORYMBIFERA; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; MULTIDRUG RESISTANT TUBERCULOSIS; MYCOBACTERIUM AVIUM; MYCOBACTERIUM KANSASII; MYCOBACTERIUM TUBERCULOSIS; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; STRUCTURE ACTIVITY RELATION; TRICHOPHYTON MENTAGROPHYTES; TRICHOSPORON ASAHII; BACTERIA; CELL PROLIFERATION; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; DRUG SCREENING; FUNGUS; HEPG2 CELL LINE; MICROBIAL SENSITIVITY TEST; SYNTHESIS;

CORYNEBACTERINEAE; MYCOBACTERIUM AVIUM; MYCOBACTERIUM KANSASII; MYCOBACTERIUM TUBERCULOSIS; POSIBACTERIA;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; BACTERIA; CELL PROLIFERATION; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; FUNGI; HEP G2 CELLS; HUMANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; ORGANOPHOSPHATES; SALICYLANILIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84892369035     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.12.016     Document Type: Article

References (28)

1. M. Kratky, J. Vinsova, E. Novotna, J. Mandikova, V. Wsol, F. Trejtnar, V. Ulmann, J. Stolarikova, S. Fernandes, S. Bhat, and J.O. Liu Tuberculosis 92 2012 434
2. M. Kratky, and J. Vinsova Curr. Pharm. Des. 17 2011 3494
3. M. Kratky, J. Vinsova, and J. Stolarikova Molecules 17 2012 12812
4. M. Kratky, J. Vinsova, E. Novotna, J. Mandikova, F. Trejtnar, and J. Stolarikova Molecules 18 2013 3674
5. M. Kratky, J. Vinsova, N.G. Rodriguez, and J. Stolarikova Molecules 17 2012 492
6. M.H. Gouy, L.P. Jordheim, I. Lefebvre, E. Cros, C. Dumontet, S. Peyrottes, and C. Perigaud Bioorg. Med. Chem. 17 2009 6340
7. S. Peyrottes, G. Coussot, I. Lefebvre, J.L. Imbach, G. Gosselin, A.M. Aubertin, and C. Perigaud J. Med. Chem. 46 2003 782
8. V.J. Stella, and K.W. Nti-Addae Adv. Drug Deliv. Rev. 59 2007 677
9. L.L. Murdock, and T.L. Hopkins J. Agric. Food Chem. 16 1968 954
10. B. Hetnarski, and R.D. O'Brien J. Agric. Food Chem. 20 1972 543
11. P.P. Mager, and A. Seese Pharmazie 37 1982 729
12. F. Kaschani, S. Nickel, B. Pandey, B.F. Cravatt, M. Kaiser, and R.A.L. van der Hoorn Bioorg. Med. Chem. 20 2012 597
13. N. Latif, F.M. Asaad, and H. Hosni Liebigs Ann. Chem. 1987 1987 495
14. N. Mibu, K. Yokomizo, T. Miyata, and K. Sumoto J. Heterocycl. Chem. 47 2010 1434
15. S.Q. Xie, A. Borazjani, M.J. Hatfield, C.C. Edwards, P.M. Potter, and M.K. Ross Chem. Res. Toxicol. 23 2010 1890
16. D.K. Nomura, C.S.S. Hudak, A.M. Ward, J.J. Burston, R.S. Issa, K.J. Fisher, M.E. Abood, J.L. Wiley, A.H. Lichtman, and J.E. Casida Bioorg. Med. Chem. Lett. 18 2008 5875
17. S.H. Zhou, X.H. Yang, S.J. Wu, G.R. Chen, and L.Y. Liu Prog. Biochem. Biophys. 37 2010 190
18. D.M. Maxwell, K.M. Brecht, I. Koplovitz, and R.E. Sweeney Arch. Toxicol. 80 2006 756
19. I.Y. Lee, T.D. Gruber, A. Samuels, M. Yun, B. Nam, M. Kang, K. Crowley, B. Winterroth, H.I. Boshoff, and C.E. Barry Bioorg. Med. Chem. 21 2013 114
20. M. Kratky, J. Vinsova, V. Buchta, K. Horvati, S. Bosze, and J. Stolarikova Eur. J. Med. Chem. 45 2010 6106
21. J.P. Krise, and V.J. Stella Adv. Drug Deliver. Rev. 19 1996 287
22. B.M. Liederer, and R.T. Borchardt J. Pharm. Sci. 95 2006 1177
23. D.I. Draganov, and B.N. La Du N.-S. Arch. Pharmacol. 369 2004 78
24. R.S. Bargota, M. Akhtar, K. Biggadike, D. Gani, and R.K. Allemann Bioorg. Med. Chem. Lett. 13 2003 1623
25. J.M. Ferriz, K. Vavrova, F. Kunc, A. Imramovsky, J. Stolarikova, E. Vavrikova, and J. Vinsova Bioorg. Med. Chem. 18 2010 1054
26. J. Kaustova Klin. Microbiol. Inf. Lek. 3 1997 115
27. M. Krátký, and J. Vinšová Molecules 17 2012 9426
28. ueous One Solution Cell Proliferation Assay, Instructions for use of products G3580, G3581 and G3582, http://worldwide.promega.com/~/media/Files/Resources/Protocols/ Technical%20Bulletins/0/ CellTiter%2096%20AQueous%20One%20Solution%20Cell%20Proliferation%20Assay%20Syst em%20Protocol.pdf.