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Synthesis and Biological Evaluation of Novel 5,8-Dibromo-2-N-substituted-1,4-Naphthoquinone Derivatives as Potential Antimicrobial Agents

Year 2018, Volume: 39 Issue: 3, 608 - 614, 30.09.2018
https://doi.org/10.17776/csj.350308

Abstract

The seven 5,8-dibromo-2-N-substituted-1,4-naphthoquinone
derivatives have been synthesized and tested for their in vitro antimicrobial
activities. The results suggest that the synthesized
2-N-substituted-1,4-naphthoquinones
have high antimicrobial activity. The diffusion capacities of the compounds are
also important for the determination of the antimicrobial activities; 2c, 2f and 2g have been
shown to be promising compounds for future studies.

References

  • [1] Hodnett E.M., Wongwiechintana C., Dunn III W.J., Marrs P., Substituted 1,4-naphthoquinones vs. the ascitic sarcoma 180 of mice, J. Med. Chem., 26 (1983) 570-574.
  • [2] Gershon H. and Shanks L., Fungitoxicity of 1,4-naphthoquinones to candida albicans and trichophyton menthagrophytes, Can. J. Microbiol., 21 (1975) 1317-1320.
  • [3] Riffel A., Medina L.F., Stefani V., Santos R.C., Bizani D., Brandelli A., In vitro antimicrobial activity of a new series of 1,4-naphthoquinones, Braz. J. Med. Biol. Res., 35 (2002) 811-818.
  • [4] Aeken S.V., Deblander J., Houwer J.D., Mosselmans T., Tehrani K.A., Unexpected reaction of 2-amino-1,4-naphthoquinone with aldehydes: new synthesis of naphtho[2,1-d]oxazole compounds, Tetrahedron 67 (2011) 512-517.
  • [5] Liu B. and Ji S-J., Facile synthesis of 2-amino-1,4-naphthoquinones catalyzed by molecular iodine under ultrasonic irradiation, Synth. Commun., 38 (2008) 1201-1211.
  • [6] Tandon V.K., Maurya H.K., Mishra N.N., Shukla P.K., Design, synthesis and biological evaluation of novel nitrogen and sülfür containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents, Eur. J. Med. Chem., 44 (2009) 3130-3137.
  • [7] Bolognesi M.L., Lizzi F., Perozzo R., Brun R., Cavalli A., Synthesis of a small library of 2-phenoxy-1,4-naphthoquinone and 2-phenoxy-1,4-anthraquione derivatives bearing anti-trypanosomal and anti-leishmanial activity, Bioorg. Med. Chem. Lett., 18 (2008) 2272-2276.
  • [8] Sayil C. and Ibis C., Synthesis and spectral properties of novel thionaphtoquinone dyes, Bull. Korean Chem. Soc.; 31 (2010) 1233-1236.
  • [9] Çakmak O., Berkil Akar K., Kaplan N., Functionalization of naphthalene: a novel synthetic route to brominated naphthoquiones, Arkivoc, 50 (2012) 274-281.
  • [10] Andrews J.M., Determination of minimum inhibition concentrations, J. Antimicrob. Chemother., 48 (2001) Suppl.S1, 5-16.
  • [11] Karadag A., Aydın A., Dede S., Tekin S., Yanar Y., Cadirci B.H., Soylu M.S., Andac O., Five novel dicyanidoaurate(I)-based complexes exhibiting significant biological activities: synthesis, characterization and three crystal structures, New J. Chem., 39 (2015) 8136-8152.
  • [12] Wiegand I., Hilpert K., Hancock R.E.W., Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances, Nat. Protoc., 3/2 (2008) 163-175.

Potansiyel Antimikrobiyal Ajanlar Olarak Yeni 5,8-Dibromo-2-N-Sübstitüe-1,4-Naftokinon Türevlerinin Sentezi ve Biyolojik Değerlendirmesi

Year 2018, Volume: 39 Issue: 3, 608 - 614, 30.09.2018
https://doi.org/10.17776/csj.350308

Abstract

Yedi adet
5,8-dibromo-2-N-sübstitüe-1,4-naftakinon türevi sentezlenmiş ve bu
bileşiklerin in vitro antimikrobiyal aktiviteleri test edilmiştir. Elde edilen
sonuçlar 2-N-sübstite-1,4-naftakinonların yüksek antimikrobiyal etkinliğe sahip
olduklarını göstermektedir. Bileşiklerin difüzyon kapasitesi de antimikrobiyal
aktivitelerin belirlenmesinde önem taşımaktadır; Sonuçlar 2c, 2f ve 2g bileşiklerinin gelecekteki
çalışmalar için umut verici bileşikler olduklarını ortaya koymuştur.

References

  • [1] Hodnett E.M., Wongwiechintana C., Dunn III W.J., Marrs P., Substituted 1,4-naphthoquinones vs. the ascitic sarcoma 180 of mice, J. Med. Chem., 26 (1983) 570-574.
  • [2] Gershon H. and Shanks L., Fungitoxicity of 1,4-naphthoquinones to candida albicans and trichophyton menthagrophytes, Can. J. Microbiol., 21 (1975) 1317-1320.
  • [3] Riffel A., Medina L.F., Stefani V., Santos R.C., Bizani D., Brandelli A., In vitro antimicrobial activity of a new series of 1,4-naphthoquinones, Braz. J. Med. Biol. Res., 35 (2002) 811-818.
  • [4] Aeken S.V., Deblander J., Houwer J.D., Mosselmans T., Tehrani K.A., Unexpected reaction of 2-amino-1,4-naphthoquinone with aldehydes: new synthesis of naphtho[2,1-d]oxazole compounds, Tetrahedron 67 (2011) 512-517.
  • [5] Liu B. and Ji S-J., Facile synthesis of 2-amino-1,4-naphthoquinones catalyzed by molecular iodine under ultrasonic irradiation, Synth. Commun., 38 (2008) 1201-1211.
  • [6] Tandon V.K., Maurya H.K., Mishra N.N., Shukla P.K., Design, synthesis and biological evaluation of novel nitrogen and sülfür containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents, Eur. J. Med. Chem., 44 (2009) 3130-3137.
  • [7] Bolognesi M.L., Lizzi F., Perozzo R., Brun R., Cavalli A., Synthesis of a small library of 2-phenoxy-1,4-naphthoquinone and 2-phenoxy-1,4-anthraquione derivatives bearing anti-trypanosomal and anti-leishmanial activity, Bioorg. Med. Chem. Lett., 18 (2008) 2272-2276.
  • [8] Sayil C. and Ibis C., Synthesis and spectral properties of novel thionaphtoquinone dyes, Bull. Korean Chem. Soc.; 31 (2010) 1233-1236.
  • [9] Çakmak O., Berkil Akar K., Kaplan N., Functionalization of naphthalene: a novel synthetic route to brominated naphthoquiones, Arkivoc, 50 (2012) 274-281.
  • [10] Andrews J.M., Determination of minimum inhibition concentrations, J. Antimicrob. Chemother., 48 (2001) Suppl.S1, 5-16.
  • [11] Karadag A., Aydın A., Dede S., Tekin S., Yanar Y., Cadirci B.H., Soylu M.S., Andac O., Five novel dicyanidoaurate(I)-based complexes exhibiting significant biological activities: synthesis, characterization and three crystal structures, New J. Chem., 39 (2015) 8136-8152.
  • [12] Wiegand I., Hilpert K., Hancock R.E.W., Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances, Nat. Protoc., 3/2 (2008) 163-175.
There are 12 citations in total.

Details

Primary Language English
Subjects Pharmacology and Pharmaceutical Sciences
Journal Section Natural Sciences
Authors

Kıymet Berkil Akar

Eda Mercan

Barış Eran

Bilge Hilal Çadırcı

Publication Date September 30, 2018
Submission Date November 9, 2017
Acceptance Date July 21, 2018
Published in Issue Year 2018Volume: 39 Issue: 3

Cite

APA Berkil Akar, K., Mercan, E., Eran, B., Çadırcı, B. H. (2018). Synthesis and Biological Evaluation of Novel 5,8-Dibromo-2-N-substituted-1,4-Naphthoquinone Derivatives as Potential Antimicrobial Agents. Cumhuriyet Science Journal, 39(3), 608-614. https://doi.org/10.17776/csj.350308