Synthesis and Biological Evaluation as a Potential Allylamine Type Antimycotics

알릴아민 항진균제의 합성과 생물학적 평가

  • Published : 2003.10.01

Abstract

Structure-activity relationship studies of allylamine type of antimycotics were carried out to evaluate the effect of naphthyl and methyl portion of naftifine. Compounds with 4-fluorophenyl(2a-5a), 2-fluorophenyl(2b-5b), 2,4-dichlorophenyl(2c-5c), 2,6-dichlorophenyl(2d-5d), 4-nitrophenyl(2e-5e), and 2,3-dihydro-benzo[1,4]dioxan-6-yl( 2f-5f) instead of naphthyl group with hydrogen(3a-3f), methyl(4a-4f), and ethyl(5a-5f) in the place of methyl in naftifine were synthesized and tested their in vitro anti-fungal activity against five different fungi. Eight compounds(3a, 5a, 3c, 4c, 4d, 5d, 5e, and 4f) showed significant antifungal activity against T. mentagrophytes. (E)-N-Ethyl-(3-phenyl-2-propenyl)-4-nitro-benzenemethaneamine(5e) displayed moderate antifungal activity against all five different fungi.

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References

  1. Antibiot. Ann. v.56 Amphotericins A and B, antibiotics produced by a streptomycete Gold,W.;Stout,H.A.;Pagano,J.F.;Donovick,R.
  2. Science v.122 Two antifungal agents produced by a soil acetinomyces Hazen,E.L.;Brown,L.
  3. J. Am. Chem. Soc. v.64 N-Allylnormorpholins Weijlard,J.;Erickson,A.E. https://doi.org/10.1021/ja01256a036
  4. Drugs of Today v.20 Imidazoles as medically important antifungal agents: An overview Robert,A.;Fromtling,Ph.D.
  5. Chemtheraphy v.17 Miconazole, a broad spectrum antimycotic agent with amtibacterial activity Van Cutsem, J. M.;Thienpont,D. https://doi.org/10.1159/000220875
  6. Drugs v.16 Econazole, a review of its antifungal activity and therapeutic efficacy Heel,R.C.;Brogden,R.N,;Speight,T.M.;Avery,G.S. https://doi.org/10.2165/00003495-197816030-00001
  7. J. Med. Chem. v.22 Antimycotic imidazole. Ⅳ. Synthesis and antifungal activity of ketoconazole, a new potent orally activity broadspectrum antifungal agent Heeres,R.J.;Backx,J.J.;Mostmans,J.H.;Van Gutsem, J. https://doi.org/10.1021/jm00194a023
  8. CRC Handbook of chemotherapeutic agents v.1 Conner,D.T.;Verderame,M.(Ed.)
  9. Drugs of the Future v.14 Saperconazole, A new potent antifungal triazole: In vitro activity spectrum and therapeutic efficacy Van Cutsem, J.;Van GerVen, F.;Janssen,P.A.J. https://doi.org/10.1358/dof.1989.014.12.109655
  10. Helv. Chim. Acta. v.61 Heterocyclic spiro-naphthalenones, Part Ⅰ: Synthesis and reactions of same spiro [(¹H-naphth-alenone)-1,3-piperidines] Berny,D.;Schun,K.
  11. J. Med. Chem. v.27 Synthesis and antifungal activity of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphth-alenemethaneamine (SF 86-327) and related allylamine derivatives with enhanced oral activity Stuetz,A.;Petranyi,G. https://doi.org/10.1021/jm00378a003
  12. J. Med. Chem. v.29 Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics Stuetz,A.Georgopoulos,A.;Grantzer,W.;Petranyi,G.;Berny,D. https://doi.org/10.1021/jm00151a019
  13. Ann. N. Y. Acad. Sci. Synthesis and structure-activity correlations within allylamine antimycotics Stuetz,A.