Bulky 1,4-benzoxazine derivatives with antifungal activity

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 11, 2009, Pages 3838-3846

  Fringuelli, Renata ^a   Giacchè, Nicola ^a   Milanese, Lara ^a   Cenci, Elio ^a   Macchiarulo, Antonio ^a   Vecchiarelli, Anna ^a   Costantino, Gabriele ^a   Schiaffella, Fausto ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

1,4 Benzoxazine; Azole antifungals; CA CYP51 inhibitors; Ketoconazole like drugs

Indexed keywords

1,4 BENZOXAZINE DERIVATIVE; 2 BUTYL 6 [[2 (2,4 DICHLOROPHENYL) 2 (1H IMIDAZOL 1 YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY] 4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 3 ONE; 6 [[2 (2,4 DICHLOROPHENYL) 2 (1H IMIDAZOL 1 YLMETHYL) 1,3 DIOXOLAN 4 YL]METHOXY] 4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 3 ONE; BENZOXAZINE DERIVATIVE; FLUCONAZOLE; KETOCONAZOLE; PIPERAZINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; STEROL 14ALPHA DEMETHYLASE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CANDIDA GLABRATA; CANDIDA KRUSEI; CANDIDA PARAPSILOSIS; CANDIDIASIS; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; CRYPTOCOCCUS NEOFORMANS; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; FUNGAL STRAIN; FUNGUS GROWTH; IN VITRO STUDY; MOLECULAR DOCKING; MOUSE; NONHUMAN; STEREOCHEMISTRY; SURVIVAL; TARGET ORGAN;

ANIMALS; ANTIFUNGAL AGENTS; BENZOXAZINES; CANDIDA; CRYPTOCOCCUS NEOFORMANS; FEMALE; MICE; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

ANIMALIA; CANDIDA; CANDIDA ALBICANS; FILOBASIDIELLA NEOFORMANS; MURINAE; MYCOBACTERIUM TUBERCULOSIS;

EID: 65549137466     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.04.051     Document Type: Article

References (28)

1. Marr K.A. Med. Mycol. 46 (2008) 293
2. Bhatti Z., Shaukat A., Almyroudis N.G., and Segal B.H. Mycopathologia 162 (2006) 1
3. Prasad R., and Kapoor K. Int. Rev. Cytol. 242 (2004) 215
4. Chang A., Neofytos D., and Horn D. Future Microbiol. 3 (2008) 463
5. Moyssakis I., Vassilakopoulos T.P., Sipsas N.V., Perakis A., Petrou A., Kosmas N., and Pangalis G.A. Int. J. Antimicrob. Agents 25 (2005) 444
6. Podust L.M., Poulos T.L., and Waterman M.R. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 3068
7. Fringuelli R., Schiaffella F., Bistoni F., Pitzurra L., and Vecchiarelli A. Bioorg. Med. Chem. 6 (1998) 103
8. Pitzurra L., Fringuelli R., Perito S., Schiaffella F., Barluzzi R., Bistoni F., and Vecchiarelli A. Antimicrob. Agents Chemother. 43 (1999) 2170
9. Schiaffella F., Guarraci A., Fringuelli R., Pitzurra L., Bistoni F., and Vecchiarelli A. Med. Chem. Res. 9 (1999) 291
10. Fringuelli R., Pietrella D., Schiaffella F., Guarraci A., Perito S., Bistoni F., and Vecchiarelli A. Bioorg. Med. Chem. 10 (2002) 1681
11. Macchiarulo A., Costantino G., Fringuelli D., Vecchiarelli A., Schiaffella F., and Fringuelli R. Bioorg. Med. Chem. 10 (2002) 3415
12. Schiaffella F., Macchiarulo A., Milanese L., Vecchiarelli A., Costantino G., Pietrella D., and Fringuelli R. J. Med. Chem. 48 (2005) 7658 13
13. Milanese L., Giacchè N., Schiaffella F., Vecchia relli A., Macchiarulo A., and Fringuelli R. ChemMedChem 2 (2007) 1208
14. Schiaffella F., Macchiarulo A., Milanese L., Vecchiarelli A., and Fringuelli R. Bioorg. Med. Chem. 14 (2006) 5196
15. Rupp B., Raub S., Marian C., and Höltje H.D. J. Comput. Aided Mol. Des. 19 (2005) 149
16. Sevrioukova I.F., Li H., Zhang H., Peterson J.A., and Poulos T.L. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 1863
17. Xiao L., Madison V., Chau A.S., Loebenberg D., Palermo R.E., and McNicholas P.M. Antimicrob. Agents Chemother. 48 (2004) 568
18. Rotstein D.M., Kertesz D.J., Walker A.M., and Swinney D.C. J. Med. Chem. 35 (1992) 2818
19. Itoh N., Sakamoto T., Miyazawa E., and Kikugawa Y. J. Org. Chem. 67 (2002) 7424
20. Wheeler K.W. J. Med. Chem. 5 (1962) 1378
21. Anaissie E.J., Karyotakis N.C., Hachem R., Dignani M.C., Rex J.H., and Paetznick V. J. Infect. Dis. 170 (1994) 384
22. Rex J.H., Galgiani J.N., Bartlett M.S., Espaniel-Ingroff A., Ghannoum M.A., Lancaster M., Odds F.C., Rinaldi M.G., and Barry A.L. Clin. Infect. Dis. 24 (1997) 235
23. Rex J.H., Nelson P.W., Paetznick V.L., Lozano-Chiu M., Espinel-Ingroff A., and Anaissie E.J. Antimicrob. Agents Chemother. 42 (1998) 129
24. Gibson F.S., Park M.S., and Rapoport H. J. Org. Chem. 59 (1994) 7503
25. Cerius-2, Accelrys, San Diego, CA.
26. Rappe A.K., Casewit C.J., Colwell K.S., Goddard W.A., and Skiff W.M. J. Am. Chem. Soc. 114 (1992) 10024
27. Bistoni F., Vecchiarelli A., Cenci E., Puccetti P., Marconi P., and Cassone A. Infect. Immun. 51 (1986) 668
28. National Committee for Clinical Laboratory Standards. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts. Approved Standards. Document M27A. Wayne, PA: National Committee for Clinical Laboratory Standards, 1997.