Synthesis and evaluation of analogues of S-adenosyl-L-methionine, as inhibitors of the E. coli cyclopropane fatty acid synthase

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 7, 2004, Pages 1661-1664

  Guérard, Christine ^a   Bréard, Maud ^a   Courtois, Fabienne ^a   Drujon, Thierry ^a   Ploux, Olivier ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Antituberculous drug; Cyclopropane fatty acid synthase; Inhibitors; S adenozyl L homocysteine sulfoxide; S adenozyl L methionine

Indexed keywords

BACTERIAL ENZYME; CYCLOPROPANE FATTY ACID SYNTHETASE; S ADENOSYLMETHIONINE; SULFONIUM DERIVATIVE; SULFOXIDE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG BINDING; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; ESCHERICHIA COLI; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN;

DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; ESCHERICHIA COLI PROTEINS; METHYLTRANSFERASES; S-ADENOSYLMETHIONINE;

EID: 17644448251     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.01.051     Document Type: Article

References (34)

1. De Meijere A. Chem. Rev. 103:2003;931.
2. Liu, H-w.; Walsh, C. T. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; J. Wiley and Sons, 1987; p 959.
3. Grogan D.W., Cronan J.E. Microb. Mol. Biol. Reviews. 61:1997;429.
4. Barry C.E., Lee R.E., Mdluli K., Sampson A.E., Schroeder B.G., Slayden R.A., Yuan Y. Prog Lipid Res. 37:1998;143.
5. Pohl S., Law J.H., Ryhage R. Biochim. Biophys. Acta. 70:1963;583.
6. Polacheck J.W., Tropp B.E., Law J.W. J. Biol. Chem. 241:1966;3362.
7. Law J.H. Acc. Chem. Res. 4:1970;199.
8. Cronan J.E., Nunn W.D., Batchelor J.G. Biochimi. Biophys. Acta. 348:1974;63.
9. Lederer E.Q. Rev. 23:1969;453.
10. Cohen T., Herman G., Chapman T.M., Kuhn D. J. Am. Chem. Soc. 96:1974;5627.
11. Buist P.H., MacLean D.B. Can. J. Chem. 59:1980;828.
12. Buist P.H., MacLean D.B. Can. J. Chem. 60:1981;371.
13. Huang C.C., Smith C.V., Glickman M.S., Jacobs W.R. Jr., Sacchettini J.C. J. Biol. Chem. 277:2002;11559.
14. Glickman M.S., Cox J.S., Jacobs W.R. Mol. Cell. 5:2000;717.
15. Taylor F.R., Grogan D.W., Cronan J.E. Methods Enzymol. 71:1981;133.
16. Wang A.-Y., Grogan D.W., Cronan J.E. Biochemistry. 31:1992;11020.
17. Boyle P.H., Davis A.P., Dempsey K.J., Hosken G.D. Tetrahedron: Asymmetry. 6:1995;2819.
18. Anderson G.L., Bussolotti D.L., Coward J.K. J. Med. Chem. 24:1981;1271.
19. +} 312].
20. 3COOH (10% w/v) and 3 times with 1 mL of water. After drying, the filter disks were transferred to a scintillation vial, and 3 mL of Optiphase HighSafe (Wallac) scintillation fluid were added and the radioactivity counted (Rackbeta, LKB, Sweeden).
21. Taylor F.R., Cronan J.E. Biochemistry. 18:1979;3292.
22. Coward J.K., Anderson G.L., Tang K.-C. Methods Enzymol. 94:1983;286.
23. Ramalingam K., Woodard R.W. Carbohydr. Res. 142:1985;123.
24. Francesconi K.A., Edmonds J.S., Stick R.V. J. Chem. Soc., Perkin Trans 1. 1992;1349.
25. +} 314].
26. 3).
27. Kuhn R., Jahn W. Chem. Ber. 98:1965;1699.
28. Borchardt R.T., Wu Y.S. J. Med. Chem. 17:1974;862.
29. +} 401].
30. Balicki R. Synth. Commun. 29:1999;2235.
31. +} 417].
32. Micetich R.G., Betageri S., Singh R., Payne P. J. Org. Chem. 52:1987;915.
33. Borchardt R.T., Pugh C.S.G. Biochemistry. 21:1982;1535.
34. Smith D.D., Norton S.J. Biochem. Biophys. Res. Commun. 94:1980;1458.