The chemistry of pseudomonic acid. 15. Synthesis and antibacterial activity of a series of 5-alkyl, 5-alkenyl, and 5-heterosubstituted oxazoles

Journal of Medicinal Chemistry

Volumn 39, Issue 2, 1996, Pages 446-457

  Brown, Pamela ^a   Davies, David T ^a   O'Hanlon, Peter J ^a   Wilson, Jennifer M ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 (1 NORMON 2 YL) 5 PHENOXYOXAZOLE; 5 (1,3 DITHIAN 2 YL) 2 (1 NORMON 2 YL)OXAZOLE; 5 [3 (METHOXYCARBONYL)PROPYL] 2 (1 NORMON 2 YL)OXAZOLE; 5 BUTYL 2 (1 NORMON 2 YL)OXAZOLE; 5 ETHOXY 2 (1 NORMON 2 YL)OXAZOLE; ISOLEUCINE TRANSFER RNA LIGASE; OXAZOLE DERIVATIVE; PSEUDOMONIC ACID; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG POTENCY; DRUG SYNTHESIS; LIPOPHILICITY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MAGNETIC RESONANCE SPECTROSCOPY; MUPIROCIN; OXAZOLES;

EID: 0030054110     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9503862     Document Type: Article

References (23)

1. Part 14: Broom, N. J. P.; Elder, J. S.; Hannan, P. C. T.; Pons, J. E.; O'Hanlon, P. J.; Walker, G.; Wilson J.; Woodall, P. The Chemistry of Pseudomonic acid Part 14. Synthesis and in vivo biological activity of heterocyclyl substituted oxazole derivatives. J. Antibiot., in press.
2. Basker, M. J.; Comber, K. R.; Clayton, J. P.; et al. Ethyl Monate A: a Semisynthetic Antibiotic Derived from Pseudomonic Acid A. In Current Chemotherapy and Infectious Diseases; Nelson, J. D., Grassi, C., Eds.; American Society for Microbiology: Washington, 1980; Vol. 1, p 471.
3. (a) Hughes, J.; Mellows, G. Inhibition of Isoleucyl Transfer-Ribonucleic Acid Synthetase in Escherichia Coli by Pseudomonic Acid. Biochem. J. 1978, 176, 305-318.
4. (b) Hughes, J.; Mellows, G. Interaction of Pseudomonic Acid with Escherichia Coli B Isoleucyl tRNA synthetase. Biochem. J. 1980, 191, 209-219.
5. Crimmin, M. J.; O'Hanlon, P. J.; Rogers, N. H.; Walker, G. The Chemistry of Pseudomonic Acid. Part 10. Preparation of Heterocyclic Derivatives. J. Chem. Soc., Perkin Trans. 1 1989, 2047-2057.
6. Crimmin, M. J.; O'Hanlon, P. J.; Rogers, N. H.; Sime, F. M.; Walker, G. The Chemistry of Pseudomonic Acid. Part 11. Dehydrative Cyclization of α-Acylamino Ketones to Oxazoles. J. Chem. Soc., Perkin Trans. 1 1989, 2059-2063.
7. Clayton, J P.; Luk, K.; Rogers, N. H. The Chemistry of Pseudomonic Acid. Part 2. The Conversion of Pseudomonic Acid A into Monic Acid A and its Esters. J. Chem. Soc., Perkin Trans. 1, 1979, 308.
8. Sime, J. T.; Pool, C. R.; Tyler, J. W. Regioselective enzymic hydrolysis in the isolation of isomers of Pseudomonic acid. Tetrahedron Lett. 1987, 28, 5169-5172.
9. Nahm, S.; Weinreb, S. M. N-Methoxy-N-methylamides as Effective Acylating Agents. Tetrahedron Lett. 1981, 22, 3815-3818.
10. Corey, E. J.; Erickson, B. W. Oxidative Hydrolysis of 1,3-Dithiane Derivatives to Carbonyl Compounds using N-Halosuccinimide Reagents. J. Org. Chem. 1971, 36, 3553.
11. Clark Still, W.; Gennari, C. Direct Synthesis of Z-unsaturated esters. A useful modification of the Horner-Emmons olefination. Tetrahedron Lett. 1983, 24, 4405-4408.
12. Tsuji, J.; Ohno, K. Decarbonylation Reactions Using Transition Metal Complexes. Synthesis 1969, 157.
13. Lindgren, B. O.; Nillson, T. Preparation of Carboxylic Acids from Aldehydes by oxidation with chlorite. Acta Chem. Scand. 1973, 27, 888.
14. Clayton, J. P.; Oliver, R. S.; Rogers, N. H.; King, T. J. The Chemistry of Pseudomonic Acid. Part 3. The rearrangement of Pseudomonic Acid A in Acid and Basic Solution. J. Chem. Soc., Perkin Trans. 1 1979, 838.
15. Clerin, D.; Fleury, J.-P. Hétérocyclisation des α-acylaminoamides. (Heterocyclization of α-acylaminoamides.) Bull. Soc. Chim. Fr. 1973 No. 11, 3127.
16. Murakami, M.; Iwanami, M. Synthesis of Pyridoxine. Synthesis of 4-methyl-5-ethoxycarbonyloxyoxazole. Bull. Chem. Soc. Jpn. 1968, 41, 726.
17. Alonso, M.; Jaao, P. The Synthesis of Ethoxycarbonyl-1,3-dioxoles and oxazoles from the Copper Catalysed thermolysis of ethyl diazopyruvate in the Presence of Ketones, Aldehydes and Nitriles. J. Heterocycl. Chem. 1980, 721.
18. Connell, R.; Scavo, F.; Helquist, P. Functionalised oxazoles from Rhodium-Catalysed Reaction of Dimethyl Diazomalonate with Nitriles. Tetrahedron Lett. 1986, 27, 5559-5562.
19. Klein, L. L.; Yeung, C. M.; Kwatu, J. C. M.; Fernandes, P. B.; Larky, P. A.; Pernet, A. G. Synthesis and Activity of Nonhydrolysable Pseudomonic Acid Analogues. J . Med. Chem. 1989, 32, 151.
20. Durekovic, A.; Flossdorf, J.; Kula, M.-R. Isolation and properties of isoleucyl tRNA synthetase from Escherichia coli MRE 600. Eur. J. Biochem. 1973, 36, 528-533.
21. Turchi, I. J.; Dewar, M. J. S. The Chemistry of Oxazoles. Chem. Rev. 1975, 75, 389.
22. A solution of 2o in 50% MeOH/water or 50% MeOH/pH 4.5 0.05 M ammonium acetate buffer was found to have completely degraded over a period of 2 h at room temperature. A solution of 2p under the same conditions showed a half-life of 20 h.
23. Zook, H. D.; Knight, J. A. Addition of hydrogen bromide to trans-4-heptenoic acid. J . Am. Chem. Soc. 1954, 76, 2302.