Antifungal 3,5-disubstituted furanones: From 5-acyloxymethyl to 5-alkylidene derivatives

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 5, 2010, Pages 1988-2000

  Šenel, Petr ^a   Tichotová, Lucie ^a   Votruba, Ivan ^b   Buchta, Vladimír ^a,c   Špulák, Marcel ^a   Kuneš, Jiří ^a   Nobilis, Milan ^a   Krenk, Ondřej ^a   Pour, Milan ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^c UNIVERSITY HOSPITAL HRADEC KRALOVE   (Czech Republic)

Author keywords

Antifungal activity; Butenolides; Cytostatic activity; Flow cytometry; Furanones; Pd catalysis; Synthesis

Indexed keywords

3 (4 BROMOPHENYL) 2,5 DIHYDROFURAN 2 ONE; 3 (4 BROMOPHENYL) 5 (3 HYDROXYPROPYLIDENE) 2,5 DIHYDROFURAN 2 ONE; 3 (4 BROMOPHENYL) 5 [(3 BROMOPHENOXY)METHYL] 2,5 DIHYDROFURAN 2 ONE; 3 (4 BROMOPHENYL) 5 [(4 HYDROXYPHENOXY)METHYL] 2,5 DIHYDROFURAN 2 ONE; 3 (4 BROMOPHENYL) 5 [(4 IODOPHENOXY)METHYL] 2,5 DIHYDROFURAN 2 ONE; 3 (4 BROMOPHENYL) 5 [(4 METHOXYPHENOXY)METHYL] 2,5 DIHYDROFURAN 2 ONE; 3 (4 BROMOPHENYL) 5 ETHOXYMETHYL 2,5 DIHYDROFURAN 2 ONE; 3 (4 BROMOPHENYL) 5 ETHYLIDENE 2,5 DIHYDROFURAN 2 ONE; 3 (4 BROMOPHENYL) 5 METHOXYMETHYL 2,5 DIHYDROFURAN 2 ONE; 3 (4 BROMOPHENYL) 5 METHYLENE 2,5 DIHYDROFURAN 2 ONE; 3 (4 BROMOPHENYL) 5 PHENOXYMETHYL 2,5 DIHYDROFURAN; 3 (4 ROMOPHENYL) 5 (2 HYDROXYETHYLIDENE) 2,5 DIHYDROFURAN 2 ONE; 3 [[4 (4 BROMOPHENYL) 5 OXO 2,5 DIHYDROFURAN 2 YL] METHOXY]BENZOIC ACID; 3,5 FURANONE DERIVATIVE; 4 [[4 (4 BROMOPHENYL) 5 OXO 2,5 DIHYDROFURAN 2 YL] METHOXY]BENZOIC ACID; 5 ACYLOXYMETHYL DERIVATIVE; 5 ALKOXYMETHYL DERIVATIVE; 5 ALKYLIDENE DERIVATIVE; 5 METHYLENE 3 (4 BROMOPHENYL) 2,5 DIHYDROFURAN 2 ONE; 5 METHYLENE FURANONE; ALKYLOXY; ARYLOXY; CYTOSTATIC AGENT; FURANONE DERIVATIVE; METHOXYMETHYL 3 [[4 (4 BROMOPHENYL) 5 OXO 2,5 DIHYDROFURAN 2 YL]METHOXY]BENZOATE; METHOXYMETHYL 4 [[4 (4 BROMOPHENYL) 5 OXO 2,5 DIHYDROFURAN 2 YL]METHOXY]BENZOATE; METHYL 4 [[4 (4 BROMOPHENYL) 5 OXO 2,5 DIHYDROFURAN 2 YL]METHOXY]BENZOATE; METHYL GROUP; PHENOXYMETHYL DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIFUNGAL ACTIVITY; ARTICLE; CELL CYCLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

ANTIFUNGAL AGENTS; APOPTOSIS; CELL LINE; CYTOSTATIC AGENTS; FURANS; HELA CELLS; HUMANS; MICROBIAL SENSITIVITY TESTS;

EID: 77249128854     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.01.030     Document Type: Article

References (34)

1. Richardson M.D. J. Antimicrob. Chemother. 56 (2005) i5
2. Kale P., and Johnson L.B. Drugs Today 41 (2005) 91
3. Spellberg B.J., Filler S.G., and Edwards Jr. J.E. Clin. Pract. 42 (2006) 244
4. Oppenheim B.A., and Herbrecht R. Clin. Infect. Dis. 21 (1995) 1145
5. Bhatti Z., Shaukat A., Almyroudis N.G., and Segal B.H. Mycopathologia 162 (2006) 1
6. De Sarro A., La Camera E., and Fera M.T. J. Chemother. 20 (2008) 661
7. La Regina G., D'Auria F.D., Tafi A., Piscitelli F., Olla S., Caporuscio F., Nencioni L., Cirilli R., La Torre F., De Melo N.R., Kelly S.L., Lamb D.C., Artico M., Botta M., Palamara A.T., and Silvestri R. J. Med. Chem. 51 (2008) 3841
8. Pfaller M.A., and Diekema D.J. Clin. Microbiol. Rev. 20 (2007) 133
9. Playford E.G., Eggimann P., and Calandra T. Curr. Opin. Infect. Dis. 21 (2008) 610
10. Pour M., Špulák M., Balšánek V., Kuneš J., Buchta V., and Waisser K. Bioorg. Med. Chem. Lett. 10 (2000) 1893
11. Pour M., Špulák M., Balšánek V., Kuneš J., and Buchta V. Bioorg. Med. Chem. 11 (2003) 2843
12. Pour M., Špulák M., Buchta V., Kubanová P., Vopršalová M., Wsól V., Fáková H., Koudelka P., Pourová H., and Schiller R. J. Med. Chem. 44 (2001) 2701
13. Buchta V., Pour M., Kubanová P., Silva L., Votruba I., Vopršalová M., Schiller R., Fáková H., and Špulák M. Antimicrob. Agents Chemother. 48 (2004) 873
14. Šnajdr I., Pavlík J., Schiller R., Kuneš J., and Pour M. Collect. Czech. Chem. Commun. 72 (2007) 1472
15. Vale-Silva L.A., Buchta V., Vokurková D., and Pour M. Bioorg. Med. Chem. Lett. 16 (2006) 2492
16. Nobilis M., Pour M., Šenel P., Pavlík J., Kuneš J., Vopršalová M., Kolářová L., and Holčapek M. J. Chromatogr., B 853 (2007) 10
17. Horimoto, A. Jpn. Kokai Tokkyo Koho 2007277137, 2007.
18. Fáková H., Pour M., Kuneš J., and Šenel P. Tetrahedron Lett. 46 (2005) 8137
19. More J.D., and Finney N.S. Org. Lett. 4 (2002) 3001
20. Tretyakov E.V., Tkachev A.V., Rybalova T.V., Gatilov Y.V., Knight D.W., and Vasilevsky S.F. Tetrahedron 56 (2000) 10075
21. Gabriele B., Salerno G., Costa M., and Chiusoli G.P. Tetrahedron Lett. 40 (1999) 989
22. Rossi R., Bellina F., and Mannina L. Tetrahedron Lett. 39 (1998) 3017
23. Rossi R., Bellina F., Biagetti M., and Mannina L. Tetrahedron Lett. 39 (1998) 7799
24. Biagetti M., Bellina F., Carpita A., Viel S., Mannina L., and Rossi R. Eur. J. Org. Chem. (2002) 1063
25. Pavlík J., Šnajdr I., Kuneš J., Špulák M., and Pour M. J. Org. Chem. 74 (2009) 703
26. Pour M., and Negishi E.-I. Tetrahedron Lett. 38 (1997) 525
27. Li X.-C., Ferreira D., Jacob M.R., Zhang Q., Khan S.I., ElSohly H.N., Nagle D.G., Smillie T.J., Khan I.A., Walker L.A., and Clark A.M. J. Am. Chem. Soc. 126 (2004) 6872
28. Dean W.D., and Blum D.M. J. Org. Chem. 58 (1993) 7916
29. Li W., Li J., Lin M., Wacharasindhu S., Tabei K., and Mansour T.S. J. Org. Chem. 72 (2007) 6016
30. Li W., Li J., Wan Z.-K., Wu J., and Massefski W. Org. Lett. 9 (2007) 4607
31. National Committee for Clinical Laboratory Standards. Reference method for broth dilution antifungal susceptibility testing of yeasts: Approved Standard, NCCLS document M27-A, 771 E. Lancaster Avenue, Villanova, PA, 19085, 1997.
32. Hocek M., Holý A., Votruba I., and Dvořáková H. J. Med. Chem. 43 (2000) 1817
33. Carmichael J., DeGraff W.G., Gazdar A.F., Minna J.D., and Mitchell J.B. Cancer Res. 47 (1987) 936
34. Havranek M., Sauerberg P., Mogensen J.P., Kratina P., Jeppesen C.B., Pettersson I., and Pihera P. Bioorg. Med. Chem. Lett. 17 (2007) 4144