A new synthetic access to furo[3,2-f]chromene analogues of an antimycobacterial

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 17, 2008, Pages 8264-8272

  Alvey, Luke ^a   Prado, Soizic ^b   Huteau, Valérie ^a   Saint Joanis, Brigitte ^a   Michel, Sylvie ^c   Koch, Michel ^c   Cole, Stewart T ^a   Tillequin, François ^c   Janin, Yves L ^a  

^a INSTITUT PASTEUR   (France)

^b MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

^c UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

2 Formylbenzoquinone; 2+3 Cycloaddition; 2+4 Cycloadditions; Antimycobacterial; Benzofuro 3,2 f 1 benzopyran; Furo 3,2 f chromene; Mycobacterium tuberculosis

Indexed keywords

2 (7,7 DIMETHYL 8,9 DIHYDRO 7H FURO[3,2 F]CHROMEN 2 YL)PYRIDINE; 2 FORMYLBENZOQUINONE; 3 (7,7 DIMETHYL 8,9 DIHYDRO 7H FURO[3,2 F]CHROMEN 2 YL)PYRIDINE; 3,3 DIMETHYL 3H BENZOFURO[3,2 F][1]BENZOPYRAN; 4 (7,7 DIMETHYL 7H FURO[3,2 F]CHROMEN 2 YL)PYRIDINE; [5 (7,7 DIMETHYL 7H FURO[3,2 F]CHROMEN 2 YL)PYRIDIN 2 YL]DIMETHYLPROPANE 1,3 DIAMINE; [6 (7,7 DIMETHYL 7H FURO[3,2 F]CHROMEN 2 YL)PYRIDIN 2 YL]DIMETHYLPROPANE 1,3 DIAMINE; ANTIMYCOBACTERIAL AGENT; BENZOFURAN DERIVATIVE; BENZOQUINONE DERIVATIVE; FURO[3,2 F]CHROMENE DERIVATIVE; FUROCHROMENE DERIVATIVE; ISOBUTYLENE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; YTTERBIUM;

ARTICLE; BACTERIAL GROWTH; CATALYSIS; CONTROLLED STUDY; CYCLOADDITION; DRUG ACTIVITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; BENZOFURANS; BENZOPYRANS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS;

EID: 50649093515     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.06.057     Document Type: Article

References (22)

1. Prado S., Ledeit H., Michel S., Koch M., Darbord J.C., Cole S.T., Tillequin F., and Brodin P. Bioorg. Med. Chem. 14 (2006) 5423
2. Prado S., Janin Y.L., Saint-Joanis B., Brodin P., Michel S., Koch M., Cole S.T., Tillequin F., and Bost P.E. Bioorg. Med. Chem. 15 (2007) 2177
3. Prado S., Toum V., Saint-Joanis B., Michel S., Koch M., Cole S.T., Tillequin F., and Janin Y.L. Synthesis (2007) 1566
4. Domschke G. J. Prakt. Chem. 32 (1966) 144
5. Iwai I., and Ide J. Chem. Pharm. Bull. 10 (1963) 926
6. Iwai I., and Ide J. Chem. Pharm. Bull. 11 (1963) 1042
7. Hlubucek J., Ritchie E., and Taylor W.C. Aust. J. Chem. 24 (1971) 2347
8. Stradi R., Pocar D., and Cassio C. J. Chem. Soc., Perkin Trans. 1 (1974) 2671
9. Kedrowski S.M.A., Bower K.S., and Dougherty D.A. Org. Lett. 9 (2007) 3205
10. Zhou G., and Corey E.J. J. Am. Chem. Soc. 127 (2006) 11958
11. von Kuser P., Frauenfelder E.F., and Eugster C.H. Helv. Chim. Acta 54 (1971) 969
12. Kraus G.A., Hoover K., and Zhang N. Tetrahedron Lett. 43 (2002) 5319
13. Valderrama J.A., Pessoa-Mahana D., Tapia R.A., Rojas de Arias A., Nakayama H., Torres S., Miret J., and Ferreira M.E. Tetrahedron 57 (2001) 8653
14. Valderrama J.A., Benites J., Cortes M., Pessoa-Mahana D., Prina E., and Fournet A. Tetrahedron 58 (2002) 881
15. Prado S., Janin Y.L., and Bost P.E. J. Heterocycl. Chem. 43 (2006) 1605
16. Noland W.E., and Kedrowski B.L. Org. Lett. 2 (2000) 2109
17. Bruce J.M., Heatley F., Ryles R.G., and Scrivens J.H. J. Chem. Soc., Perkin Trans. 2 (1980) 860
18. Mahboobi S., and Wiegrebe W. Arch. Pharm. 321 (1988) 175
19. Schmidt A., Mordhorst T., Fleischhauer H., and Jeschke G. ARKIVOC (2005) 150
20. Palomino J.-C., Martin A., Camacho M., Guerra H., Swings J., and Portaels F. Antimicrob. Agents Chemother. 46 (2002) 2720
21. Noyori R., Yokoyama K., and Hayakawa Y. Org. Synth. Coll. VI (1988) 520
22. LaMattina J.L. J. Heterocycl. Chem. 20 (1983) 533