The Chemistry of Pseudomonic Acid Part 14 Synthesis and In Vivo Biological Activity of Heterocyclyl Substituted Oxazole Derivatives

The Journal of Antibiotics

Volumn 48, Issue 11, 1995, Pages 1336-1344

  Broom, N J P ^a   Elder, J S ^a   Hannan, P C T ^a   Pons, J E ^a   O'Hanlon, P J ^a   Walker, G ^a   Wilson, J ^a   Woodall, P ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; ANTIINFECTIVE AGENT; OXAZOLE DERIVATIVE; PSEUDOMONIC ACID; PSEUDOMONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; REACTION ANALYSIS;

ANIMAL; ANTIBIOTICS; COMPARATIVE STUDY; FURANS; HUMAN; ISOXAZOLES; MICE; MUPIROCIN; OXAZOLES; PYRAZOLES; PYRIDINES; SEPSIS; STAPHYLOCOCCAL INFECTIONS; THIAZOLES; THIOPHENES;

EID: 0028805477     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.7164/antibiotics.48.1336     Document Type: Article

References (15)

1. Forrest, A. K.; P. J. O'Hanlon & G. Walker: The chemistry of pseudomonic acid, Part 13. Modifications at C-12 to C-14. Tetrahedron 1994: 10739–10748, 1994
2. Crimmin, M. J.; P.J. O'Hanlon, N.H. Rogers, F.M. Sime & G. Walker: The chemistry of pseudomonic acid, Part 11. Dehydrative cyclisation of a-acylamino ketones to oxazoles. J. Chem. Soc. Perkin Trans. 1 1989: 2059–2063, 1989
3. Walker, G.; P. Brown, M. J. Crimmin, A. K. Forrest, P. J. O'Hanlon & J. E. Pons: New antibacterial agents: synthesis and antibacterial activity of heterocyclic derivatives of pseudomonic acid. In Recent Advances in the Chemistry of Anti-Infective Agents. Eds. P. H. Bentley & R. Ponsford, pp. 106—116, Royal Society of Chemistry, Cambridge (UK), 1993
4. Clayton, J. P.; K. Luk & N. H. Rogers: 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: 308–313, 1979
5. Blazevic, N; D. Kolbah, B. Belin, V. Sunjic & F. Kajfez: Hexamethylenetetramine, a versatile reagent in organic synthesis. Synthesis 1979: 161 — 176, 1979
6. Clemo, G. R.; T. Holmes & G. C. Leitch: The synthesis of phenyl-and pyridyl-glyoxalines. J. Chem. Soc. 1938: 753–755, 1938
7. Hamada, Y.; S. Morita & T. Shioiri: A new synthesis of 4-methoxycarbonyloxazoles using diethyl phosphorocyanidate (DEPC) and its application to the synthesis of 3-amino-4-hydroxytetrones. Heterocycles 17: 321 — 324, 1982
8. Houwing, H. A.; J. Wildeman & A. M. Van Leusen: Synthesis of 2,5-disubstituted oxazoles from aldehydes and N-(tosylmethyl)imino synthons. Application to the synthesis of pimprinine analogues. J. Heterocyclic Chem. 18: 1133–1139, 1981
9. Fournari, P. & J. P. Chane: Researches in the heterocyclic series. IV. Synthesis of disubstituted thiophenes and application of polarographic analysis to the separation of nitro-isomers. Bull. Chim. Soc. Fr. 1963: 479–484, 1963
10. Lejeune, R. & L. Thunus: Contributions to the study of mercaptopyridine carboxylic acids. III. Preparation of the esters, ethers, and ether-esters of the mercaptopyridine carboxylic acids. J. Pharm. Belg. 35: 98 ~ 102, 1980
11. Bradlow, H. L. & C. A. Vanderwerf: Studies on the acid hydrolysis of a-halogenated pyridine compounds. J. Org. Chem. 14: 509–515, 1949
12. Noyce, D. S. & G. V. Kaiser: The solvolysis of furylmethylcarbinol derivatives. J. Org. Chem. 34: 1008-1012, 1969
13. Chung, N. M. & H. Tieckelmann: Alkylations of heterocyclic ambident anions. 4. Alkylation of 5-carbethoxy-and 5-nitro-2-pyridone salts. J. Org. Chem. 35: 2517–2520, 1970
14. Henecka, H. & P. Kurtz: Funktionelle N-derivative der carboxylgruppe. In Methoden der Organischen Chemie, Vol. 8. Ed., E. Muller, pp. 647— 713, Georg Thieme Verlag, Stuttgart, 1952
15. Chiarino, D.; M. Napoletano & A. Sala: 1,3-Dipolar cycloaddition synthesis of 3-bromo-5-substituted isoxazoles, useful intermediates for the preparation of pharmacologically active compounds. J. Heterocyclic Chem. 24: 43–46, 1987