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Synthesis and Antifungal Activity of New Heterocyclic Compounds

Year 2013, Volume: 38 Issue: 1, 103 - 107, 01.03.2013

Abstract

Purpose:The objective of this study was to describe the synthesis of 2-arylthio-N-(2-methoxydibenzo[b,d]furan-3-yl)acetamide derivatives as heterocyclic compounds and focused on their potential antifungal effects against fungi species. Method: The reaction of 2-chloro-N-(2-methoxydibenzo[b,d]furan-3-yl)acetamide with various aromatic thiols gave 2-arylthio-N-(2-methoxydibenzo[b,d]furan-3-yl)acetamide derivatives. Antifungal activities of the synthesized compounds have been evaluated using microbroth dilution method. Results: Four new heterocyclic compounds were synthesized. All compounds were as effective as ketoconazole against T. harzianum, A. ochraceus, C. albicans, whilst the compounds were more effective than ketoconazole against F. solani, F. moniliforme, F. culmorum. Conclusion: All synthesized compounds showed significant antifungal activity when compared with ketoconazole.

References

  • Pfaller MA. The epidemiology of invasive mycosesnarrowing the gap. Clin Infect Dis. 1998; 27:1148-50.
  • Marr KA, Carter RA, Crippa F, Wald A, Corey L. Epidemiology and outcome of mould infections in hematopoietic stem cell transplant recipients. Clin Infect Dis. 2002; 34:909-17.
  • Hood S, Denning DW. Treatment of fungal infection in AIDS. J Antimicrob Chemoth. 1996; 37:71-85.
  • Rees JR, Pinner RW, Hajjeh RA. The epidemiological features of invasive mycotic infections in the San Francisco, 1992-1993: Results of population-based laboratory active surveillance. Clin Infect Dis. 1993; 27:1138-40.
  • Polak A. The past, present and future of antimycotic combination therapy. Mycoses. 1999; 42:355-70.
  • Musiol R, Jampilek J, Buchta V, Silva L, Niedbala H, Podeszwa B, et al. Antifungal properties of new series of quinolone derivatives. Bioorg Med Chem. 2006; 14:3592-8.
  • Rao VS, Srinivas K. Modern drug discovery process. J Bioinform Seq Anal. 2011; 2: 89-94.
  • Ryu CK, Kim YH, Im HA, Kim JY, Yoon JH, Kim A. Synthesis and antifungal activity of 6,7-bis(arylthio)quinazoline-5,8-diones and furo[2,3-f]quinazolin-5ols. Bioorg Med Chem Lett. 2012; 22:500-3.
  • Ryu CK, Shim JY, Chae MJ, Choi IH, Han JY, Jung OJ, et al. Synthesis and antifungal activity of 2/3arylthio- and 2,3-bis(arylthio)-5-hydroxy-/5-methoxy1,4-naphthoquinones. Eur J Med Chem. 2005; 40:438-44.
  • Ryu CK, Sun YJ, Shim JY, You HJ, Choi KU, Lee H. Synthesis and antifungal activity of 6,7-bis-[s(aryl)thio]-5,8-quinolinediones. Arc Pharmacal Res. 2002; 25:795-800.
  • Venkatachalam TK, Barreto J, Kreher U, Reutens DC, Spiccia L. Synthesis, characterization and coordination chemistry of dibenzofuran derivatives of 1,4,7,10-tetraazacyclododecane. Inorg Chim Acta. 2010; 363:2896-904
  • Winn WC, Allen SD, Janda WM, Koneman EW, Procop GW, Schreckenberger PC, et al. Koneman’s Color Atlas and Textbook of Diagnostic Microbiology, 6th Ed. Baltimore and Philadelphia, Lippincott Williams & Wilkins, 2006.
  • Espinel-Ingroff A. In Vitro Fungicidal Activities of Voriconazole, Itraconazole, and Amphotericin B against Opportunistic Moniliaceous and Dematiaceous Fungi. J Clin Microbiol. 2001; 39:954 Yaz
  • ışma Adresi / Address for Correspondence: Dr. Zafer Asım Kaplancıklı Anadolu University Graduate Scholl of Health Sciences ESKİŞEHİR e-mail: zakaplan@anadolu.edu.tr. geliş tarihi/received :11.07.2012 kabul tarihi/accepted:07.09.2012

Yeni Heterosiklik Bileşiklerin sentezleri ve Antifungal Etkileri

Year 2013, Volume: 38 Issue: 1, 103 - 107, 01.03.2013

Abstract

Amaç: Bu çalışmanın amacı, heterosiklik bileşik olarak, 2-ariltiyo-N-(2-metoksidibenzo[b,d]furan-3-il)asetamid türevlerinin sentezleri ve mantar türlerine karşı etkilerini araştırmaktır. Yöntem: 2-Kloro-N-(2-metoksidibenzo[b,d]furan-3-il)asetamid ile uygun aromatik tiyollerin reaksiyonu 2-ariltiyo-N-(2-metoksidibenzo[b,d]furan-3-il)asetamid türevlerini verdi. Sentezlenen bu bileşiklerin antifungal aktiviteleri microbroth dilution method kullanılarak araştırıldı. Bulgular: Dört yeni heterosiklik bileşik sentezlendi. Bileşiklerin tamamı F. solani, F. moniliforme, F. culmorum"a karşı Ketokonazol"den daha aktif çıkarken, C. albicans, T. harzianum, A. ochraceus"e karşı Ketokonazol ile aynı etkiyi göstermiştir. Sonuç: Ketokonazol ile kıyaslandığında, sentezlenen tüm bileşikler önemli derecede antifungal etki göstermişlerdir.

References

  • Pfaller MA. The epidemiology of invasive mycosesnarrowing the gap. Clin Infect Dis. 1998; 27:1148-50.
  • Marr KA, Carter RA, Crippa F, Wald A, Corey L. Epidemiology and outcome of mould infections in hematopoietic stem cell transplant recipients. Clin Infect Dis. 2002; 34:909-17.
  • Hood S, Denning DW. Treatment of fungal infection in AIDS. J Antimicrob Chemoth. 1996; 37:71-85.
  • Rees JR, Pinner RW, Hajjeh RA. The epidemiological features of invasive mycotic infections in the San Francisco, 1992-1993: Results of population-based laboratory active surveillance. Clin Infect Dis. 1993; 27:1138-40.
  • Polak A. The past, present and future of antimycotic combination therapy. Mycoses. 1999; 42:355-70.
  • Musiol R, Jampilek J, Buchta V, Silva L, Niedbala H, Podeszwa B, et al. Antifungal properties of new series of quinolone derivatives. Bioorg Med Chem. 2006; 14:3592-8.
  • Rao VS, Srinivas K. Modern drug discovery process. J Bioinform Seq Anal. 2011; 2: 89-94.
  • Ryu CK, Kim YH, Im HA, Kim JY, Yoon JH, Kim A. Synthesis and antifungal activity of 6,7-bis(arylthio)quinazoline-5,8-diones and furo[2,3-f]quinazolin-5ols. Bioorg Med Chem Lett. 2012; 22:500-3.
  • Ryu CK, Shim JY, Chae MJ, Choi IH, Han JY, Jung OJ, et al. Synthesis and antifungal activity of 2/3arylthio- and 2,3-bis(arylthio)-5-hydroxy-/5-methoxy1,4-naphthoquinones. Eur J Med Chem. 2005; 40:438-44.
  • Ryu CK, Sun YJ, Shim JY, You HJ, Choi KU, Lee H. Synthesis and antifungal activity of 6,7-bis-[s(aryl)thio]-5,8-quinolinediones. Arc Pharmacal Res. 2002; 25:795-800.
  • Venkatachalam TK, Barreto J, Kreher U, Reutens DC, Spiccia L. Synthesis, characterization and coordination chemistry of dibenzofuran derivatives of 1,4,7,10-tetraazacyclododecane. Inorg Chim Acta. 2010; 363:2896-904
  • Winn WC, Allen SD, Janda WM, Koneman EW, Procop GW, Schreckenberger PC, et al. Koneman’s Color Atlas and Textbook of Diagnostic Microbiology, 6th Ed. Baltimore and Philadelphia, Lippincott Williams & Wilkins, 2006.
  • Espinel-Ingroff A. In Vitro Fungicidal Activities of Voriconazole, Itraconazole, and Amphotericin B against Opportunistic Moniliaceous and Dematiaceous Fungi. J Clin Microbiol. 2001; 39:954 Yaz
  • ışma Adresi / Address for Correspondence: Dr. Zafer Asım Kaplancıklı Anadolu University Graduate Scholl of Health Sciences ESKİŞEHİR e-mail: zakaplan@anadolu.edu.tr. geliş tarihi/received :11.07.2012 kabul tarihi/accepted:07.09.2012
There are 14 citations in total.

Details

Primary Language Turkish
Journal Section Research
Authors

Zafer Asım Kaplancıklı This is me

Mehlika Dilek Altıntop This is me

Gülhan Turan-zitouni This is me

Ahmet Özdemir

Rasime Demirel This is me

Usama Abu Mohsen This is me

Weiam Hussein This is me

Publication Date March 1, 2013
Published in Issue Year 2013 Volume: 38 Issue: 1

Cite

MLA Kaplancıklı, Zafer Asım et al. “Yeni Heterosiklik Bileşiklerin Sentezleri Ve Antifungal Etkileri”. Cukurova Medical Journal, vol. 38, no. 1, 2013, pp. 103-7.