Research Article
Synthesis and Biological Evaluation of Novel 5,8-Dibromo-2-N-substituted-1,4-Naphthoquinone Derivatives as Potential Antimicrobial Agents
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.
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
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 | Research Article |
| Authors | |
| Submission Date | November 9, 2017 |
| Acceptance Date | July 21, 2018 |
| Publication Date | September 30, 2018 |
| DOI | https://doi.org/10.17776/csj.350308 |
| IZ | https://izlik.org/JA72NP22CH |
| Published in Issue | Year 2018 Volume: 39 Issue: 3 |
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