Synthesis and biological activity of novel tricyclic β-lactams

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 5, 1996, Pages 525-528

  Biondi, Stefano ^a   Gaviraghi, Giovanni ^a   Rossi, Tino ^a  

^a GSK   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; BETA LACTAM DERIVATIVE; IMIPENEM; MEROPENEM;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; MINIMUM INHIBITORY CONCENTRATION; NUCLEAR MAGNETIC RESONANCE;

EID: 0029971644     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00061-3     Document Type: Article

References (19)

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3. For recent reviews on β-lactam antibiotics see: Neuhaus, F.C.; Georgopapadakou, N.H. in Emerging Targets in Antibacterial and Antifungal Chemotherapy, Sutcliffe, J.; Georgopapadakou, N.H. Ed. Chapman and Hall, New York, 1992; Georgopapadakou, N.H. Antimicrobial Agents Ann. 1988, 3. 409; Southgate, R.; Elson, S. in Progress in the Chemistry of Organic Natural Products, Herz, W.; Grisebach, H.; Kirby, G.W.; Tamm, C., Springer Verlag: New York, 1985; p. 1; Durckheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem. Int. Ed. Engl. 1985, 24, 180, Recent Advances in the Chemistry of β- Lactam Antibiotics; Brown, A. G.; Roberts, S. M.; The Royal Society of Chemistry: Burlington House, Cambridge, U.K. 1984; Georgopapadakou, N.H. Ann. Rep. Med. Chem. 1983, 18. 119.
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18. 3OH (60ml) and 2,6-lutidine (2.5ml) was added. The solution was stirred at reflux for 5 hours, cooled to 23°C and concentrated to give an oil which was dissolved in diethyl ether and washed with a pH=3 citrate buffer. The organic layer was dried, concentrated and purified by flash chromatography to give compound 14 as a colourless oil (630mg, 51%).
19. 2=3.5Hz), 4.11 (m, 1H), 3.40-3.30 (m, 2H), 3.14 (s, 3H), 2.34-2.20 (m, 1H), 1.85-1.50 (m, 2H), 1.20 (m, 1H), 1.11 (d, 3H, J=6.6Hz).