Design and synthesis of novel 5-acetylthiomethyl oxazolidinone analogs

Synthetic Communications

Volumn 40, Issue 6, 2010, Pages 789-798

  Chen, Lei ^a   Wang, Jian Wei ^a   Hai, Li ^a   Wang, Guang Ming ^b   Wu, Yong ^a  

^a SICHUAN UNIVERSITY   (China)

^b Chengdu Jinbei Sci and Tech Co Ltd   (China)

Author keywords

Antibacterial agent; Drug resistant; Oxazolidinone; Synthesis

Indexed keywords

[[3 (3 FLUORO 4 MORPHOLINYLPHENYL) 2 OXO 5 OXAZOLIDINYL]METHYL]THIOACETATE; [[3 [3 FLUORO 4 (1 IMIDAZOLYL)PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]THIOACETATE; [[3 [3 FLUORO 4 (1 PIPERIDINYL)PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]THIOACETATE; [[3 [3 FLUORO 4 (1 PYRAZOLYL)PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]THIOACETATE; [[3 [3 FLUORO 4 (1 PYRROLIDINYL)PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]THIOACETATE; [[3 [3 FLUORO 4 (1 PYRROLYL)PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]THIOACETATE; [[3 [3 FLUORO 4 (4 ACETYL 1 PIPERAZINYL)PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]THIOACETATE; [[3 [3 FLUORO 4 (4 METHYL 1 PIPERAZINYL)PHENYL] 2 OXO 5 OXAZOLIDINYL]METHYL]THIOACETATE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG DESIGN; DRUG SYNTHESIS; INFRARED RADIATION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

EID: 77349107948     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902756197     Document Type: Article

References (26)

1. Emori, T. G.; Gaynes, R. P. An overview of nosocomial infections, including the role of the microbiology laboratory. Clin. Microbiol. Rev. 1993, 6, 428-442.
2. Jones, R. N. Resistance patterns among nosocomial pathogens: Trends over the past few years. Chest 2001, 119, 397S-404S.
3. Nicolau, D. Clinical and economic implications of antimicrobial resistance for the management of community-acquired respiratory tract infections. J. Antimicrob. Chemother. 2002, 50, 61-70.
4. Pfefferkorn, J. A.; Larsen, S. D.; Huis, C. V.; Sorenson, R.; Barton, T.; Winters, T.; Auerbach, B.; Wu, C.; Wolfram, T. J.; Cai, H.; Welch, K.; Esmaiel, N.; Davis, J.; Bousley, R.; Olsen, K.; Mueller, S. B.; Mertz, T. Substituted oxazolidinones as novel NPC1L1 ligands for the inhibition of cholesterol absorption. Bioorg. Med. Chem. Lett. 2008, 18, 546-553.
5. Means, J. A.; Katz, S.; Nayek, A.; Anupam, R.; Hines, J. V.; Bergmeier, S. C. Structure-activity studies of oxazolidinone analogs as RNA-binding agents. Bioorg. Med. Chem. Lett. 2006, 16, 3600-3604.
6. Bergmeier, S. C.; Katz, S. J. A method for the parallel synthesis of multiply substituted oxazolidinones. J. Comb. Chem. 2002, 4, 162-166.
7. Gregory, W. A.; Brittelli, D. R.; Wang, C. L. J.; Kezar, H. S.; Carlson, R. K.; Park, C. H.; Corless, P. F.; Miller, S. J.; Rajagopalan, P.; Wuonola, M. A.; McRipley, R. J.; Eberly, V. S.; See, A. M.; Forbes, M. Antibacterials: Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines, 2: The "A" group. J. Med. Chem. 1990, 33, 2569-2578.
8. Reck, F.; Zhou, F.; Eyermann, C. J.; Kern, G.; Carcanague, D.; Ioannidis, G.; Illingworth, R.; Poon, G.; Gravestock, M. B. Novel substituted (pyridin-3-yl)phenyloxazolidinones: Antibacterial agents with reduced activity against monoamine oxidase a and increased solubility. J. Med. Chem. 2007, 50, 4868-4881.
9. Alice, H. L.; Robert, W. M.; Thomas, J. V.; Keith R. M. The oxazolidinone eperezolid binds to the 50S ribosomal subunit and competes with binding of chloramphenicol and lincomycin. Antimicrob. Agents Chemother. 1997, 41, 2127-2131.
10. Steve, M. S.; Hiroyuki, A.; Clelia, M. G.; Dean, L. S. The oxazolidinone linezolid inhibits initiation of protein synthesis in bacteria. Antimicrob. Agents Chemother. 1998, 42, 3251-3255.
11. Alan, H. M.; Douglas, J. B.; John, D. T.; Ronald, N. J. Spectrum and potency evaluation of a new oxazolidinone, linezolid: Report from the SENTRY Antimicrobial Surveillance Program, 1998-2000. Diagnostic Microbiol. Infect. Dis. 2002, 43, 65-73.
12. Sattigeri, V. J.; Soni, A.; Singhal, S.; Khan, S.; Pandya, M.; Bhatejab, B.; Tarun Mathur, P.; Rattan, A.; Khanna, J. M.; Mehta, A. Synthesis and antimicrobial activity of novel thiazolidinones. Arkivoc 2005, 2, 46-59.
13. Wang, C. L. J.; Gregory, W. A.; Wuonola, M. A. Chlral synthesis of dup 721, a new antibacterial agent. Tetrahedron 1989, 45, 1323-1326.
14. Ronald, D. G.; Paul, C. S.; Mary, B. G.; Swathi, K.; Karen, D.; John, P. Q. Infections due to vancomycin-resistant enterococcus faecium resistant to linezolid. Lancet 2001, 357, 1179.
15. Johnson, A. P.; Tysall, L.; Stockdale, M. W.; Woodford, N.; Kaufmann, M. E.; Warner, M.; Livermore, D. M.; Asboth, F.; Allerberger, F. J. Emerging linezolid-resistant Entero-coccus faecalis and Enterococcus faecium isolated from two Austrian patients in the same intensive care unit. Eur. J. Clin. Microbiol. Infect. Dis. 2002, 21, 751-754.
16. Ryukou, T.; Yoshiei, T.; Yayoi, T.; Tomio, S.; Toshihiko, Y.; Nobuhiko, I.; Noriyuki, K.; Eiichi, O.; Osamu, N. Structure-activity relationship (SAR) studies on oxazolidinone antibacterial agents, 1: Conversion of 5-substituent on oxazolidinone. Chem. Pharm. Bull. 2001, 49, 347-352.
17. Ryukou, T.; Yoshiei, T.; Yayoi, T.; Masatoshi, T.; Toshihiko, Y.; Nobuhiko, I.; Noriyuki, K.; Eiichi, O.; Osamu, N. Structure-activity relationship (SAR) studies on oxazolidinone antibacterial agents, 2: Relationship between lipophilicity and antibacterial activity in 5-thiocarbonyl oxazolidinones. Chem. Pharm. Bull. 2001, 49, 353-360.
18. Ryukou, T.; Yoshiei, T.; Yayoi, T.; Masatoshi, T.; Nobuhiko, I.; Noriyuki, K.; Eiichi, O.; Osamu, N. Structure-activity relationship (SAR) studies on oxazolidinone antibacterial agents, 3: Synthesis and evaluation of 5-thiocarbamate oxazolidinones. Chem. Pharm. Bull. 2001, 49, 361-367.
19. Braj, B. L.; Vidya, B. L.; Brijesh, K. S.; Prashant, B. K.; Purvi, P. Novel tetrahydro-thienopyridyl oxazolidinone: An antibacterial agent. Bioorg. Med. Chem. 2004, 12, 4557-4564.
20. Shingo, Y.; Kazuo, O.; Masakazu, F. Thiazolidine derivative and pharmaceutical composition containing the same. PCT Int. Appl. 9422857, 13 Oct. 1994.
21. Genim, M. J.; Allwine, D. A.; Anderson, D. J.; Barbachyn, M. R.; Emmert, D. E.; Garmon, S. A.; Graber, D. R.; Grega, K. C.; Hester, J. B.; Hutchinson, D. K.; Morris, J.; Reischer, R. J.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H. Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl) oxazolidinones with expanded activity against the fastidious Gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis. J. Med. Chem. 2000, 43, 953-970.
22. Keshav, D. P.; Dattatraya, S. M.; Shriram, P. M.; Dattatrya, Y. R.; Vinayak, G. S.; Yati, C.; Nitin, S.; Subhash, B. S.; John, D. S. N.; Vithalbhai, P. M. Substituted piperidino phenyloxazolidinones having antimicriobial activity with improved in vivo efficacy. PCT Int. Appl. 2005054234, 16 Jun. 2005.
23. Yasumichi, F. Cyclopropyl group substituted oxazolidinone antibiotics and derivatives thereof. PCT Int. Appl. 2005005398, 20 Jan. 2005.
24. Keol, R. J.; Bin, I. W.; Hwang, C. C.; Hak, C. S.; Ho, L. T. Novel oxazolidinone derivatives. PCT Int. Appl. 2005058886, 30 Jun. 2005.
25. Gregory, W. A.; Brittelli, D. R.; Wang, C. L. J.; Wuonola, M. A.; McRipley, R. J.; Eustice, D. C.; Eberly, V. S.; Bartholomew, P. T.; Slee, A. M.; Forbes, M. Antibacterials: Synthesis and structure-activity studies of 3-aryl-2-oxooxazoliding, 1: The "B" group. J. Med. Chem. 1989, 32, 1673-1681. (Pubitemid 19204345)
26. Brickner, S. J.; Hutchinson, D. K.; Barbachyn, M.; Manninen, R. P. R.; Ulanowicz, D. A.; Garmon, S. A.; Grega, K. C.; Hendges, S. K.; Toops, D. S.; Ford, C. W.; Zurenko, G. E. Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant Gram-positive bacterial infections. J. Med. Chem. 1996, 39, 673-679.