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

Yıl 2018, Cilt: 39 Sayı: 3, 608 - 614, 30.09.2018
https://doi.org/10.17776/csj.350308

Öz

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.

Kaynakça

  • [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

Yıl 2018, Cilt: 39 Sayı: 3, 608 - 614, 30.09.2018
https://doi.org/10.17776/csj.350308

Öz

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.

Kaynakça

  • [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.
Toplam 12 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Eczacılık ve İlaç Bilimleri
Bölüm Natural Sciences
Yazarlar

Kıymet Berkil Akar

Eda Mercan

Barış Eran

Bilge Hilal Çadırcı

Yayımlanma Tarihi 30 Eylül 2018
Gönderilme Tarihi 9 Kasım 2017
Kabul Tarihi 21 Temmuz 2018
Yayımlandığı Sayı Yıl 2018Cilt: 39 Sayı: 3

Kaynak Göster

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