Synthesis of isothiochroman 2,2-dioxide and 1,2-benzooxathiin 2,2- dioxide gyrase B inhibitors

Tetrahedron Letters

Volumn 41, Issue 11, 2000, Pages 1741-1745

  Peixoto, Christophe ^a   Laurin, Patrick ^a   Klich, Michel ^a   Dupuis Hamelin, Claudine ^b   Mauvais, Pascale ^b   Lassaigne, Patrice ^b   Bonnefoy, Alain ^b   Musicki, Branislav ^a  

^a Medicinal Chemistry   (France)

^b Infectious Disease Group   (France)

Author keywords

Antibiotics; Glycosidation; Hydrogen bonding; Structure activity

Indexed keywords

1,2 BENZOOXATHIIN 2,2 DIOXIDE; COUMARIN DERIVATIVE; GYRASE INHIBITOR; ISOTHIOCHROMAN 2,2 DIOXIDE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; LIPOPHILICITY; NONHUMAN; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0034635901     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00044-7     Document Type: Article

References (20)

1. For reviews on structure and mode of action of coumarins on DNA gyrase, see: (a) Reece, R. J.; Maxwell, A. Crit. Rev. Biochem. Mol. Biol. 1991, 26, 335-375.
2. (b) Levine, C.; Hiasa, H.; Marians, K. J. Biochim. Biophys. Acta 1998, 1400, 29-43.
3. (c) Berger, J. M. Biochim. Biophys. Acta 1998, 1400, 3-18.
4. (d) Maxwell, A. Biochem. Soc. Trans. 1999, 27, 48-53.
5. (a) Laurin, P.; Ferroud, D.; Klich, M.; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 1999, 9, 2079-2084.
6. (b) Haesslein, J.-L.; Klich, M.; Laurin, P.; Musicki, B.; Periers, A.-M. PCT. Int. Appl. WO 9935155, 1999. Chem. Abstr. 1999, 131, 454249.
7. (c) Laurin, P.; Ferroud, D.; Schio, L.; Klich, M.; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 1999, 9, 2875-2880.
8. (d) Ferroud, D.; Collard, J.; Klich, M.; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 1999, 9, 2881-2886.
9. (e) Periers, A. M.; Laurin, P.; Ferroud, D.; Haesslein, J. L.; Klich, M.; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 2000, 10, 161-165.
10. (a) Wigley, D. B.; Davies, G. J.; Dodson, E. J.; Maxwell, A.; Dodson, G. Nature 1991, 351, 624-629.
11. (b) Lewis, R. J.; Singh, O. M. P.; Smith, C. V.; Maxwell, A.; Skarzynsky, T.; Wonacott, A. J.; Wigley, D. B. J. Mol. Biol. 1994, 241, 128-130.
12. (c) Lewis, R. J.; Singh, O. M. P.; Smith, C. V.; Skarzynski, T.; Maxwell, A.; Wonacott, A. J.; Wigley, D. B. EMBO J. 1996, 15, 1412-1420.
13. (d) Tsai, F. T. F.; Singh, O. M. P.; Skarzynski, T.; Wonacott, J. A.; Weston, S.; Tucker, A.; Pauptit, R. A.; Breeze, A.; Poyser, J. P.; O'Brien, R.; Ladbury, J. E.; Wigley, D. B. Proteins: Struct., Funct., Genet. 1997, 28, 41-52.
14. Houbion, J. A.; Miles, J. A.; Paton, J. A. Org. Prep. Proced. Int. 1979, 11, 27-32.
15. This mixture of regioisomers was tested without separation.
16. Jones, G.; Stantforth, S. P. In Organic Reactions; John Willey & Sons: New York, 1997; Vol. 49, pp. 1-330.
17. Corey, E. J.; Gilman, N. W.; Ganem, B. E. J. Am. Chem. Soc. 1968, 90, 5616.
18. Partition coefficient P expressed as logP for the compounds 29 and 30 was determined according to Ref. 9 as 3.1 and 5.2, respectively.
19. (a) Dross, K.; Sonntag, C.; Mannhold, R. J. Chromatogr. 1993, 639, 287-294.
20. (b) Dross, K.; Sonntag, C.; Mannhold, R. J. Chromatogr. 1994, 673, 113-124.