Chiral derivatives of Butenafine and Terbinafine: synthesis and antifungal activity

Tetrahedron

Volumn 65, Issue 47, 2009, Pages 9807-9813

  Fuglseth, Erik ^a   Otterholt, Eli ^b   Høgmoen, Hanne ^a   Sundby, Eirik ^a   Charnock, Colin ^b   Hoff, Bård Helge ^a  

^a NORWEGIAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Norway)

^b OSLO METROPOLITAN UNIVERSITY   (Norway)

Author keywords

Amines; Antifungal agents; Butenafine; Chiral; Substituent effects

Indexed keywords

ANTIFUNGAL AGENT; BUTENAFINE; N(4 TERT BUTYLBENZYL) 2 FLUORO N METHYL 1 (NAPHTHALEN 1 YL)ETHANAMINE; N(4 TERT BUTYLBENZYL) 2,2 DIFLUORO N METHYL 1 (NAPHTHALEN 1 YL)ETHANAMINE; N(4 TERT BUTYLBENZYL) 2,2,2 TRIFLUORO N METHYL 1 (NAPHTHALEN 1 YL)ETHANAMINE; N(4 TERT BUTYLBENZYL)N METHYL 1 (NAPHTHALEN 1 YL)ETHANAMINE; N(4 TERT BUTYLBENZYL)N METHYL 1 (NAPHTHALEN 1 YL)PROPAN 1 AMINE; N,6,6 TRIMETHYL N[1 (NAPHTHALEN 1 YL)PROPYL]HEPT 2 EN 4 YN 1 AMINE; N,6,6 TRIMETHYL N[1 (NAPHTHALEN 8 YL)ETHYL]HEPT 2 EN 4 YN 1 AMINE; N,6,6 TRIMETHYL N[2,2,2 TRIFLUORO 1 (NAPHTHALEN 1 YL)ETHYL]HEPT 2 EN 4 YN 1 AMINE; N[2 FLUORO 1 (NAPHTHALEN 1 YL)ETHYL]N 6,6 TRIMETHYLHEPT 2 EN 4 YN 1 AMINE; N[2,2 DIFLUORO 1 (NAPHTHALEN 1 YL)ETHYL]N 6,6 TRIMETHYLHEPT 2 EN 4 YN 1 AMINE; TERBINAFINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CRYPTOCOCCUS; CRYPTOCOCCUS NEOFORMANS; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; FUNGAL STRAIN; FUNGICIDAL ACTIVITY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; TRICHOSPORON CUTANEUM;

CRYPTOCOCCUS DIFFLUENS; FILOBASIDIELLA NEOFORMANS; TRICHOSPORON CUTANEUM;

EID: 70349972674     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.09.067     Document Type: Article

References (35)

1. Sanglard D., Kuchler K., Ischer F., Pagani J.L., Monod M., and Bille J. Antimicrob. Agents Chemother. 39 (1995) 2378-2386
2. Osborne C.S., Leitner I., Hofbauer B., Fielding C.A., Favre B., and Ryder N.S. Antimicrob. Agents Chemother. 50 (2006) 2234-2236
3. Rocha E.M.F., Gardiner R.E., Park S., Martinez-Rossi N.M., and Perlin D.S. Antimicrob. Agents Chemother. 50 (2006) 2533-2536
4. Favre B., Ghannoum M., and Ryder N. Med. Mycol. 42 (2004) 525-529
5. Williamson P.R., Zhang S., Panepinto J., Hu G., Waterman S.R., Park Y.D., and Shin S. Curr. Enzyme Inhib. 4 (2008) 186-193
6. Nelson R.T., and Lodge J.K. Mycota 13 (2006) 237-266
7. Waters L., and Nelson M. Expert Opin. Pharmacother. 6 (2005) 2633-2644
8. Bisson G.P., Lukes J., Thakur R., Mtoni I., and MacGregor R.R. S. Afr. Med. J. 98 (2008) 724-725
9. Brouwer A.E., van Kan H.J.M., Johnson E., Rajanuwong A., Teparrukkul P., Wuthiekanun V., Chierakul W., Day N., and Harrison T.S. Antimicrob. Agents Chemother. 51 (2007) 1038-1042
10. Sugita T., Saito M., Ito T., Kato Y., Tsuboi R., Takeuchi S., and Nishikawa A. Microbiol. Immunol. 47 (2003) 945-950
11. Kataoka-Nishimura S., Akiyama H., Saku K., Kashiwa M., Mori S., Tanikawa S., Sakamaki H., and Onozawa Y. Cancer 82 (1998) 484-487
12. Ryder N.S., and Favre B. Rev. Contemp. Pharmacother. 8 (1997) 275-287
13. Lin P.C., Adak A.K., Ueng S.H., Huang L.D., Huang K.T., Ho J.a.A., and Lin C.C. J. Org. Chem. 74 (2009) 4041-4048
14. Gokhale V.M., and Kulkarni V.M. Bioorg. Med. Chem. 8 (2000) 2487-2499
15. Gokhale V.M., and Kulkarni V.M. J. Med. Chem. 42 (1999) 5348-5358
16. Nussbaumer P., Petranyi G., and Stuetz A. J. Med. Chem. 34 (1991) 65-73
17. Nussbaumer P., Dorfstaetter G., Leitner I., Mraz K., Vyplel H., and Stuetz A. J. Med. Chem. 36 (1993) 2810-2816
18. Nussbaumer P., Dorfstaetter G., Grassberger M.A., Leitner I., Meingassner J.G., Thirring K., and Stuetz A. J. Med. Chem. 36 (1993) 2115-2120
19. Nussbaumer P., Leitner I., and Stuetz A. J. Med. Chem. 37 (1994) 610-615
20. Nussbaumer P., Leitner I., Mraz K., and Stuetz A. J. Med. Chem. 38 (1995) 1831-1836
21. Ji H., Zhang W., Zhou Y., Lu J., Zhu J., Li K., Chen W., and Liu N. Yaoxue Xuebao 33 (1998) 188-193
22. Maeda, T., Yamamoto, T., Takase, M., Sasaki, K., Arika, T., Yokoo, M., Hashimoto, R., Amemiya, K.; Koshikawa, S. EP 164697, 1985.
23. Chen W.P., Liu L.L., and Yang J.Q. Yaoxue Xuebao 24 (1989) 895-905
24. Ji H., Zhang W., Zhou Y., Lu J., Li K., Zhu J., and Liu N. Yaoxue Xuebao 32 (1997) 593-599
25. Kloetzel M.C., and Wildman W.C. J. Org. Chem. 11 (1946) 390-394
26. Fuglseth E., Krane Thvedt T.H., Førde Møll M., and Hoff B.H. Tetrahedron 64 (2008) 7318-7323
27. Katoch-Rouse R., Pavlova O.A., Caulder T., Hoffman A.F., Mukhin A.G., and Horti A.G. J. Med. Chem. 46 (2003) 642-645
28. Hanch C., Leo A., and Hoekman D. Exploring QSAR-Hydrophobic, Electronic and Steric Constants (ACS Professional Reference Book) (1995), American Chemical Society, Washington, DC
29. Provine H., and Hadley S. J. Clin. Microbiol. 38 (2000) 537-541
30. National Committee for Clinical Laboratory Standards. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts. Approved standard M27-A (1997), National Committee for Clinical Laboratory Standards, Wayne, PA
31. Bouziane A., Carboni B., Bruneau C., Carreaux F., and Renaud J.L. Tetrahedron 64 (2008) 11745-11750
32. Surya Prakash G.K., Hu J., and Olah G.A. J. Fluorine Chem. 112 (2001) 357-362
33. Fuji K., Node M., Kawabata T., and Fujimoto M. J. Chem. Soc., Perkin Trans. 1 (1987) 1043-1047
34. Konno T., Takehana T., Mishima M., and Ishihara T. J. Org. Chem. 71 (2006) 3545-3550
35. Stanetty P., and Wallner H. Arch. Pharm. (Weinheim, Ger.) 326 (1993) 341-350