The Antifungal Activities of some 6-[N-(halophenyl)amino]-7-Chloro-5,8-Quinolinediones against Candida Species

  • Published : 1994.12.01

Abstract

A series of 6-[N-(halophenyl)amino]-7-chloro-5, 8-quinolinedione derivatives 1-10 were tested for antifungal susceptibilities, in vitro, aginst pathogenic Candida species such as C. ablbicans, C glabrata, C. krusei, C. parapsilosis and C. tropicalis. The MICs were determined by the standard macrodilution techniques, according to the NCCLS 1992 guidelines. The 6-[N-(halo-standard macrodilution techniques, according to the NCCLS 1992 gidelines. The 6-[N-(halo-phenyl)amino]-7-chloro-5, 8-quinolinedione derivatives showed generally potent antifungal activities against pathogenic Candida species. Among them, derivative 1, 2, 5, and 7 showed more potent antifungal activities than kietoconazole. All derivatives 1-10 had specially potent activities against C. torpicalis. Derivative 1 and 2 containing 9N-3, 4-dihalo-phenyl)amino moiety exhibited the potent antifugal activities. Derivative 2 with (3, 4-dichlorophenyl)amino substitutent was the most effetive in preventing the growth of Candida species at MICs 4.mu.g/ml respectively.

Keywords

References

  1. J. Med. Chem. v.14 5,8-Quinolinequinone analogs which inhibit mitocondrial succinoxidase Bowman,C.M.;Porter,T.H.;Skelton,F.S.;Folkers,K.
  2. Antiosxidant in theraphy and preventive medicine-Advances in experimental medicine and biology v.264 Effect of superoside dismutase on the autoxidation of hydroquinones formed during DT-diaphorase catalysis and glutathione nucleophilic addition. Cadenas,E.;Ernster,L.;Emerit,I.(ed.);Packer,L.(ed.);Auclair,C.(ed.)
  3. Lacet v.338 Yeast susceptibility testing Dopouy-Camet,J.;Paugam,A.;Tourte-Schaefer,C.
  4. J. Clin. Microbiol. v.30 Collaborative comparison of broth macrodilution and microdilution antifungal susceptibility tests Espinel Ingroff,A.;Kish,Jr.C.W.;Kerkering,T.M.;Fromtling,R.A.;Bartizal,K.;Galgiani,J.N.;Villareal,K.;Pfaller,M.A.;Gerarden,T.M.;Rinaldi,G.;Fothergill,A.
  5. J. Clin. Microbiol. v.29 no.6 Comparision study of broth macrodilution and microdilution antifungal susceptibility tests Espinel-Ingroff,A.;Kerkering,T.M.;Goldson,P.R.;Shadmy,S.
  6. J. Med. Vet, Mycol. v.30 no.suppl.1 Standardization of antifungal susceptibility testing Galgiani,J.N.;Rinaldi,M.G.;Polak,A.M.;Pfaller,M.A.
  7. J. Antibiotics v.41 Mechanism of inhibition of reverse transcriptase by quinone antibiotics Hafuri,Y.;Takemori,E.;Oogose,K.;Inouye,Y.;Nakamura,S.
  8. J. Antibiotics v.40 The quinolinequione as the minimum entity for reverse transcriptase-inhibitory activity of streptonigrin Inouye,Y.;Take,Y.;Keiko,O.;Kobo,A.;Nakamura,S.
  9. Antibiotics in laboratory medicine,(3rd ed.) Antifungal drug Mcginnis,M.R.;Rindali,M.G.;Lorian,V.(eds.)
  10. Document M27-P. National Committee for Cliical Laboratory Standards Reference method for broth dilution antifungal susceptibility testing of yeasts. Proposed standaed NCLS;National Committee for Clinical Labortory Standards
  11. SOD and active oxygen modulators-pharmacology and clinical trials Oyanagui,Y(eds.)
  12. J. Clin. Microbiol. v.26 Multicenter evaluation of four methods of yeast inoculum preparation Pfaller,M.A;Burmeister,L.;Bartlett,M.S.;Rinaldi,M.G.
  13. J. Med. Chem. v.14 Synthesis of 5,8-quinolinequinones as inhibitors fo coenzyme Q and antimalarials Porter,T.H.;Skelton,F.S.;Folkers,K.
  14. Clin, Microbiol. Rev. v.6 Antifungal susceptibility testing Rex,J.H.;Pfaller,M.A.;Rinaldi,M.G.;Polak,A.;Galgiani,J.N.
  15. Arch. Biochem. Biophys. v.191 The site of inhibition mitcochondrial electron transfer by coenzyme Q analogs Roberts,H.;Choo,W.M.;Smith,S.C.;Marzuki,S.;Linnane,A.W.;Porter,T.H;Folkers, K.
  16. Arch. Pharm. Res. v.17 no.3 The synthesis of 6-(N-arylamoni)-7-chloro-5,8-quinolinedione dericatives for evaluation of antifiungal activities Ryu,C.K.;Kim,H.J.
  17. Clin. Infe. Disease v.17 no.Suppl. 2 Antifungal susceptibility tests of yeasts : A brief overview Sheehan,D.J.;Espinel Ingroff,A.;Moork,D.J.;Webb,C.D.
  18. Austrian patent;220 Fungicides Wagner,A.;Beck,W.;Diskus,A.
  19. J. Heterocycl. Chem. v.24 Streptonigrin and lavandamycin partial structure. A probe for the minium potent pharmacophore of the antitumor anitibiotics Yasuda,M.;Boger,D.L.
  20. Chem. Abstract v.57 Fungicides Wagner,A.;Beck,W.;Diskus,A.
  21. Chem. Abstract v.56 Fungicides Wagner,A.;Beck,W.;Diskus,A.