Effects of varied substituents on the antibacterial activity of triazolylmethyl oxazolidinones

Archiv der Pharmazie

Volumn 345, Issue 10, 2012, Pages 790-803

  Phillips, Oludotun A ^a   Udo, Edet E ^a   Abdel Hamid, Mohammed E ^a   Varghese, Reny ^a  

^a KUWAIT UNIVERSITY   (Kuwait)

Author keywords

Antibacterial activity; Gram positive bacteria; Guanidino oxazolidinone; Linezolid; Triazolylmethyl oxazolidinone

Indexed keywords

2 [4 [2 FLUORO 4 [5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL) METHYL] 2 OXOOXAZOLIDIN 3 YL]PHENYL]PIPERAZIN 1 YL]ACETAMIDE; 2 [4 [2 FLUORO 4 [5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL] 2 OXOOXAZOLIDIN 3 YL]PHENYL]PIPERAZIN 1 YL] 2 OXOETHANAMINIUM 2,2,2 TRIFLUOROACETATE; 3 [3 [FLUORO 4 [4 (5 NITROFURAN 2 CARBONYL)PIPERAZIN 1 YL]PHENYL] 5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [3 FLUORO 4 (4 ISONICOTINOYLPIPERAZIN 1 YL)PHENYL] 5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [3 FLUORO 4 (4 NICOTINOYLPIPERAZIN 1 YL)PHENYL] 5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [3 FLUORO 4 [4 (2 ISOTHIOCYANATOACETYL)PIPERAZIN 1 YL]HENYL] 5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [3 FLUORO 4 [4 (3 FLUOROBENZOYL)PIPERAZIN 1 YL]PHENYL] 5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [3 FLUORO 4 [4 (3 METHOXYBENZOYL)PIPERAZIN 1 YL] PHENYL] 5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [3 FLUORO 4 [4 (3 METHYLBENZOYL)PIPERAZIN 1 YL]PHENYL] 5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [3 FLUORO 4 [4 (3 NITROBENZOYL)PIPERAZIN 1 YL]PHENYL] 5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [3 FLUORO 4 [4 (FURAN 2 CARBONYL)PIPERAZIN 1 YL] PHENYL] 5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL] OXAZOLIDIN 2 ONE; 3 [3 FLUORO 4 [4 (THIOPHENE 2 CARBONYL)PIPERAZIN 1 YL]PHENYL] 5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [4 [4 (3,5 DINITROBENZOYL)PIPERAZIN 1 YL] 3 FLUOROPHENYL] 5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [4 [4 (3,5 DINITROBENZYL)PIPERAZIN 1 YL] 3 FLUOROPHENYL] 5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL] OXAZOLIDIN 2 ONE; 3 [4 [4 (4 CHLOROBENZOYL)PIPERAZIN 1 YL] 3 FLUOROPHENYL] 5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 5 [(1H 1,2,3 TRIAZOL 1 YL)METHYL] 3 (4 (4 (3,5 DINITROBENZYL)PIPERAZIN 1 YL] 3 FLUOROPHENYL]OXAZOLIDIN 2 ONE; 5 [(1H 1,2,3 TRIAZOL 1 YL)METHYL] 3 [4 [4 (3,5 DINITROBENZOYL)PIPERAZIN 1 YL] 3 FLUOROPHENYL]OXAZOLIDIN 2 ONE; ANTIINFECTIVE AGENT; ETHYL 2 (1,3 DITHIOLAN 2 YLIDENE) 3 [4 [2 FLUORO 4 [5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL] 2 OXOOXAZOLIDIN 3 YL]PHENYL]PIPERAZIN 1 YL] 3 OXOPROPANOATE; ETHYL 3 [4 [2 FLUORO 4 [5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL] 2 OXOOXAZOLIDIN 3 YL]PHENYL]PIPERAZIN 1 YL] 3 OXOPROPANOATE; ETHYL 3 [4 [4 [5 [(1H 1,2,3 TRIAZOL 1 YL)METHYL] 2 OXOOXAZOLIDIN 3 YL] 2 FLUOROPHENYL]PIPERAZIN 1 YL] 3 OXOPROPANOATE; ETHYL 5 [4 [2 FLUORO 4 [5 [(4 METHYL 1H 1,2, 3 TRIAZOL 1 YL)METHYL] 2 OXOOXAZOLIDIN 3 YL]PHENYL]PIPERAZIN 1 YL] 5 OXOPENTANOATE; METHYL 4 [4 [2 FLUORO 4 [5 [(4 METHYL 1H 1,2,3 TRIAZOL 1 YL)METHYL] 2 OXOOXAZOLIDIN 3 YL]PHENYL]PIPERAZIN 1 YL] 4 OXOBUTANOATE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; ENTEROCOCCUS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; MORAXELLA CATARRHALIS; NONHUMAN; PRIORITY JOURNAL; STAPHYLOCOCCUS;

ANTI-BACTERIAL AGENTS; DRUG RESISTANCE, BACTERIAL; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MICROBIAL SENSITIVITY TESTS; MORAXELLA (BRANHAMELLA) CATARRHALIS; OXAZOLIDINONES; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84867008865     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.201100332     Document Type: Article

References (15)

1. R. Wise, On behalf of the BSAC Working Party on The Urgent Need: Regenerating Antibacterial Drug. J. Antimicrob. Chemother. 2011, DOI: 10.1093/jac/dkr261
2. F. R. de Castro, O. R. Naranjo, J. A. Marco, J. S. Violán, Semin. Respir. Crit. Care Med. 2009, 30 (2), 161-171.
3. M. H. Wilcox, Expert Opin. Pharmacother. 2005, 6, 2315-2326.
4. J. A. Ippolito, Z. F. Kanyo, D. Wang, F. J. Franceschi, P. B. Moore, T. A. Steitz, E. M. Duffy, J. Med. Chem. 2008, 51, 3353-3356.
5. G. Poce, G. Zappia, G. C. Porretta, B. Botta, M. Biava, Expert Opin. Ther. Patents 2008, 18 (2), 97-121.
6. O. A. Phillips, E. E. Udo, A. A. M. Ali, N. Al-Hasawi, Bioorg. Med. Chem. 2003, 11, 35-41.
7. O. A. Phillips, E. E. Udo, A. A. M. Ali, S. Samuel, Eur. J. Med. Chem. 2007, 42, 214-225.
8. O. A. Phillips, E. E. Udo, A. A. M. Ali, S. Samuel, Eur. J. Med. Chem. 2009, 44, 3217-3227.
9. F. Reck, F. Zhou, M. Girardot, G. Kern, C. J. Eyermann, N. J. Hales, R. R. Ramsay, M. B. Gravestock, J. Med. Chem. 2005, 48, 499-506.
10. X. J. Wang, N. Wu, G. J. Du, S. Q. Zhao, M. Yan, L. Q. Gu, Arch. Pharm. Chem. Life Sci. 2009, 342, 377-385.
11. S. J. Brickner, D. K. Hutchinson, M. R. Barbachyn, P. R. Manninnen, D. A. Ulanowicz, et al., J. Med. Chem. 1996, 39, 673-679.
12. E. Kabha, C. Jacquement, G. Pembouong, N. Mignet, D. Scherman, J. Herscovici, Bioorg. Med. Chem. 2008, 16, 4003-4008.
13. D. S. Dodd, A. P. Kozikowski, Tet. Lett. 1994, 35 (7), 977-980.
14. National Committee for Clinical Laboratory Standards. 1997, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically, 4th edition, Approved standard. NCCLS document M7-A4. National Committee for Clinical Laboratory Standards, Villanova, PA.
15. O. A. Phillips, L. H. Sharaf, M. E. Abdel-Hamid, R. Varghese, Med. Princ. Pract. 2011, 20, 51-59.