Synthesis of a 2-indolylphosphonamide derivative with inhibitory activity against yersiniabactin biosynthesis

Tetrahedron Letters

Volumn 48, Issue 35, 2007, Pages 6080-6083

  Bisseret, Philippe ^a   Thielges, Sabine ^a   Bourg, Stéphane ^a   Miethke, Marcus ^b   Marahiel, Mohamed A ^b   Eustache, Jacques ^a  

^a UNIVERSITÉ DE HAUTE ALSACE   (France)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Atherton Todd reaction; Indole; Phosphonamidate; Plague; Yersiniabactin

Indexed keywords

2 INDOLYLPHOSPHONAMIDE DERIVATIVE; AMIDE; PHOSPHATE; PHOSPHORUS DERIVATIVE; SALICYLIC ACID; UNCLASSIFIED DRUG; YERSINIABACTIN;

ADENYLATION; ARTICLE; BIOSYNTHESIS; CATALYSIS; NONHUMAN; PROTEIN DOMAIN; PROTEIN SYNTHESIS INHIBITION; SYNTHESIS; YERSINIA PESTIS;

YERSINIA PESTIS;

EID: 34547471588     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.150     Document Type: Article

References (19)

1. Crosa J.H., and Walsh C.T. Microbiol. Mol. Biol. Rev. 66 (2002) 223-249
2. Vergne A.F., Walz A.J., and Miller M.J. Nat. Prod. Rep. 17 (2000) 99-116
3. Perry R.D., Balbo P.B., Jones H.A., Fetherston J.D., and DeMoll E. Microbiology 145 (1999) 1181-1190
4. Perry R.D., and Fetherston J.D. Clin. Microbiol. Rev. 10 (1997) 35-66
5. Gomez J.E., and McKinney J.D. Tuberculosis 84 (2004) 29-44
6. Ferreras J.A., Ryu J.-S., Lello F.D., Tan D.S., and Quadri L.E.N. Nat. Chem. Biol. 1 (2005) 29-32
7. Miethke M., Bisseret P., Beckering C.L., Vignard D., Eustache J., and Marahiel M.A. FEBS J. 273 (2006) 409-419
8. Somu R.V., Boshoff H., Qiao C., Bennett E.M., Barry III C.E., and Aldrich C.C. J. Med. Chem. 49 (2006) 31-34
9. Vannada J., Bennett E.M., Wilson D.J., Boshoff H.I., Barry III C.E., and Aldrich C.C. Org. Lett. 8 (2006) 4707-4710
10. Atherton F.R., Openshaw H.T., and Todd A.R. J. Chem. Soc. (1945) 660-663
11. Atherton F.R., and Todd A.R. J. Chem. Soc. (1947) 674-678
12. Jacobsen N.E., and Bartlett P.A. J. Am. Chem. Soc. 103 (1981) 654-657
13. Phosphoramidite 11 was prepared by adding diisopropylamine (2 equiv) at room temperature and under argon atmosphere to a THF solution of commercial chlorodimethylphosphite (1 equiv); after stirring for 2 h, a white solid was formed that was removed by filtration, and concentration in vacuo resulted in the crude phosphoramidite as a colorless liquid.
14. No improvement was obtained by using a reverse addition involving the transfer of the lithio-indolyl derivative at -50 °C to a THF solution of 11.
15. 3 (9:1, v/v), 300 K). δ 152.43, 137.31, 136.63, 134.70, 134.14, 132.85, 132.70, 130.85, 126.79, 124.43, 121.47, 115.46, 115.23, 90.77, 28.07.
16. We also performed the reaction with (N,N)-dibenzoyl-2,3-O-isopropylidene-adenosine without better success. For each experiment, the reaction was followed for 12 h.
17. Thielges S., Bisseret P., and Eustache J. Org. Lett. 7 (2005) 681-684
18. Ochiai M., Toyonari M., Nagaoka T., Chen D.-W., and Kida M. Tetrahedron Lett. 38 (1997) 6709-6712
19. 2: final curve value, x: inhibitor concentration, p: curve slope.