Synthesis and antibacterial activity of some thio trinems.

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 15, 1997, Pages 2061-2066

  Biondi, Stefano ^a   Piga, Elisabetta ^a   Rossi, Tino ^a   Vigelli, Gilberto ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOACYLASE; BETA LACTAMASE; IMIPENEM; TRIBACTAM; TRINEM DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTEROIDES FRAGILIS; CHIRALITY; CLOSTRIDIUM PERFRINGENS; DRUG SYNTHESIS; ENZYME INHIBITION; ESCHERICHIA COLI; HUMAN; IN VITRO STUDY; REACTION ANALYSIS; STAPHYLOCOCCUS AUREUS; STEREOCHEMISTRY; STRAIN DIFFERENCE;

EID: 0030751908     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00360-0     Document Type: Article

References (23)

1. a) Tamburini, B.; Perboni, A.; Rossi, T.; Donati, D.; Andreotti, D.; Gaviraghi, G.; Carlesso, R.; Bismara, C.; Eur Pat. Appl. EP 0416953 A2, 1991; Chem. Abstr. 1992, 116, 235337t.
2. a) Tamburini, B.; Perboni, A.; Rossi, T.; Donati, D.; Andreotti, D.; Gaviraghi, G.; Carlesso, R.; Bismara, C.; Eur Pat. Appl. EP 0416953 A2, 1991; Chem. Abstr. 1992, 116, 235337t.
3. b) Perboni, A.; Rossi, T.; Gaviraghi, G.; Ursini, A.; Tarzia, G.; WO 9203437, 1992; Chem; Abstr. 1992, 117, 7735m.
4. b) Perboni, A.; Rossi, T.; Gaviraghi, G.; Ursini, A.; Tarzia, G.; WO 9203437, 1992; Chem; Abstr. 1992, 117, 7735m.
5. For a recent review on trinems see: Biondi, S.; In ANTI-INFECTIVES Recent Advances in Chemistry and structure activity Relationships; Bentley, P.H.; O'Hanlon, P.J.; Eds.; RSC: Cambridge; Special Publication No.198; 1997, pp 86-100.
6. a) Di Modugno, E.; Erbetti, I.; Ferrari, L.; Galassi, G.; Hammond, S.M.; Xerri, L.; Antimicrob. Agents Chemother. 1994, 38, 2362.
7. b) Andreotti, D.; Rossi, T.; Gaviraghi, G.; Donati, D.; Marchioro, C.; Di Modugno, E.; Perboni, A.; Bioorg. Med. Chem. Lett. 1996, 6, 491.
8. For a recent total syntheses of Sanfetrinem see: Hanessian, S.; Rozema, M.J.; J. Am. Chem. Soc. 1996, 118, 9884.
9. (3R,4R,1'R)-(+)-4-acetoxy-3[1'(tert-butyldimethylsilyloxy)ethyl]- azetidin-2-one 3 is commercially available from Aldrich Chemical Company Inc. Milwaukee, WI, USA.
10. Di Fabio, R.; Feriani, A.; Gaviraghi, G.; Rossi, T.; Bioorg. Med. Chem. Lett. 1996, 6, 2589.
11. During our studies a patent claiming thio compounds belonging to the same class was published by Takeda Chemical Industries Ltd. : Sendai, M.; Miwa, T.; Eur. Pat. Appl. EP 0422596 A2, 1991.
12. House, H.O.; Czuba, L.J.; Gall, M.; Olmstead, H.D.; J. Org. Chem. 1969, 34, 2324.
13. a) Afonso, A.; Hon, F; Weinstein, J.; Ganguli, A.K.; McPhail, A.T. J. Am. Chem. Soc. 1982, 104, 6138;
14. b) Yoshida, A.; Hayashi, T.; Takeda, N.; Oida, S.; Ohki, E. Chem. Pharm. Bull., 1983, 31, 768.
15. Perboni, A.; Tamburini, B.; Rossi, T.; Donati, D.; Tarzia, G.; Gaviraghi, G.; In Recent Advances in the Chemistry of AntiInfective Agents; Bentley, P.H.; Posford, R.; Eds.; RSC: Cambridge 1992; pp 21-35.
16. We were unable to detect the presence of regioisomers of compounds 26 i.e. deriving from the lithium enolate obtained by deprotonation at position 4 of the 3-thiopyranone.
17. The use of LDA resulted in lower yields.
18. a) Woodward R. B.; In Recent Advances in the Chemistry Of β-Lactam Antibiotics, Elks, J., Ed.; Spec. Pub. N.28; Roy. Soc. Chem.; London; 1977; cap. 18.
19. a) Woodward R. B.; In Recent Advances in the Chemistry Of β-Lactam Antibiotics, Elks, J., Ed.; Spec. Pub. N.28; Roy. Soc. Chem.; London; 1977; cap. 18.
20. b) Scartazzini, R.; Peter, H.; Bickel, H.; Heusler, K.; Woodward, R.B.; Helv. Chim. Acta 1972, 55, 408.
21. Gaviraghi G.; In Proceedings of the XIIIth International Symposium on Medicinal Chemistry, Muller, J.C.; Ed.; Editions Scientifiques Elsevier 1995; pp 467S-478S.
22. 4. The solvent was removed under reduced pressure to give a foam which was purified by flash chromatography eluting with a mixture of ethyl acetate / cyclohexane in a 20 / 80 ratio to give 700 mg of intermediate 27b. Compound 27b was dissolved in xylene (70 ml) and heated at 100°C for 2 hrs. The reaction mixture was cooled at room temperature and the solvent removed under reduced pressure to give an oil which was purified by flash chromatography eluting with a mixture of cyclohexane / ethyl acetate in a 95 / 5 ratio obtaining 320 mg of compound 28b.
23. The yield is based on recovered starting material. Bioorganic & Medicinal Chemistry Letters, Vol. 7, No. 15, pp. 2067-2070, 1997