Design, synthesis, and evaluation of 1-(N-benzylamino)-2-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-2-ols as antifungal agents

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 6, 2008, Pages 1820-1824

  Giraud, Francis ^a   Logé, Cédric ^a   Pagniez, Fabrice ^a   Crepin, Damien ^a   Le Pape, Patrice ^a   Le Borgne, Marc ^a  

^a UNIVERSITÉ DE NANTES   (France)

Author keywords

Antifungal agents; Azide; Candida albicans; CYP51 inhibitors; Docking; H bond acceptor; Homology model; Microwave irradiation; Oxirane; Triazole

Indexed keywords

1 (N BENZYLAMINO) 2 PHENYL 3 (1H 1,2,4 TRIAZOL 1 YL)PROPAN 2 OL DERIVATIVE; ANTIFUNGAL AGENT; BENZYLAMINE DERIVATIVE; FLUCONAZOLE; ITRACONAZOLE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITOR INTERACTION; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR MODEL; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANTIFUNGAL AGENTS; ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; DRUG DESIGN; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; PROPANOLS; STRUCTURE-ACTIVITY RELATIONSHIP;

CANDIDA ALBICANS;

EID: 40949114620     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.02.027     Document Type: Article

References (18)

1. Na Y.M., Le Borgne M., Pagniez F., Le Baut G., and Le Pape P. Eur. J. Med. Chem. 38 (2003) 75
2. Pagniez, F.; Le Pape, P.; Na, Y. M.; Lebouvier, N.; Le Borgne, M.; Le Baut, G. Abstracts of paper, 10th Congress of the European Confederation of Medical Mycology, Wroclaw, Poland, June 17-20, 2004; P023.
3. Sheng C., Zhang W., Ji H., Zhang M., Song Y., Xu H., Zhu J., Miao Z., Jiang Q., Yao J., Zhou Y., Zhu J., and Lu J. J. Med. Chem. 49 (2006) 2512
4. Lebouvier N., Giraud F., Corbin T., Na Y.M., Le Baut G., Marchand P., and Le Borgne M. Tetrahedron Lett. 47 (2006) 6479
5. Lebouvier N., Pagniez F., Duflos M., Le Pape P., Na Y.M., Le Baut G., and Le Borgne M. Bioorg. Med. Chem. Lett. 17 (2007) 3686
6. Kempf D.J., De Lara E., Stein H.H., Cohen J., and Platnner J.J. J. Med. Chem. 30 (1987) 1978 Synthesis of 1-azido-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol (4). To a solution of 2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)-1,2-epoxypropane (3) (4.36 g, 16.14 mmol) in 50 mL of methanol was added sodium azide (3.15 g, 48.42 mmol). Then ammonium chloride (1.95 g, 36.48 mmol) was added and the solution was refluxed for 15 h. Mixture was diluted with water and product was extracted with dichloromethane.
7. Fringuelli F., Pizzo F., Rucci M., and Vaccaro L. J. Org. Chem. 68 (2003) 7041
8. Shiozaki M., Arai M., Kobayashi Y., Kasuya A., Miyamoto S., Furukawa Y., Takayama T., and Haruyama H. J. Org. Chem. 59 (1994) 4450
9. Kamal A., Srinivasa K., Reddy B., Prasad R., Hari Babu A., and Venkata Ramana A. Tetrahedron Lett. 45 (2004) 6517
10. Mangelinckx S., Boeykens M., Vliegen M., Van der Eycken J., and De Kimpe N. Tetrahedron Lett. 46 (2005) 525
11. 2)
12. aliph.), 3318 (ν O-H). MS m/z 423.1 (M+H).
13. Bolognesi M.L., Andrisano V., Bartolini M., Banzi R., and Melchiorre C. J. Med. Chem. 48 (2005) 24
14. +).
15. Compounds 8a and 9a were prepared from 6a and 7a according to the same protocol as described for compound 5 but the reaction time was reduced to 1.5 h. Products were purified on silica gel column chromatography (ethanol/dichloromethane 1:10).
16. Pagniez F., and Le Pape P. J. Mycol. Med. 11 (2001) 73
17. Lebouvier, N. Ph.D. Thesis, Université de Nantes, Nantes Atlantique Universités, October 2004.
18. Giraud, F. Ph.D. Thesis, Université de Nantes, Nantes Atlantique Universités, October 2007.