Research Article

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

Volume: 39 Number: 3 September 30, 2018
Kıymet Berkil Akar , Eda Mercan , Barış Eran , Bilge Hilal Çadırcı
PDF Download
Cumhuriyet Science Journal Cover Cumhuriyet Science Journal
EN TR

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.

Keywords

1, 4-Naphthoquinone, nucleophilic substitution, antimicrobial activity, antimicrobial activity

References

  1. [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. [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. [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. [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. [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. [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. [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. [8] Sayil C. and Ibis C., Synthesis and spectral properties of novel thionaphtoquinone dyes, Bull. Korean Chem. Soc.; 31 (2010) 1233-1236.
  9. [9] Çakmak O., Berkil Akar K., Kaplan N., Functionalization of naphthalene: a novel synthetic route to brominated naphthoquiones, Arkivoc, 50 (2012) 274-281.
  10. [10] Andrews J.M., Determination of minimum inhibition concentrations, J. Antimicrob. Chemother., 48 (2001) Suppl.S1, 5-16.

Details

Primary Language

English

Subjects

Pharmacology and Pharmaceutical Sciences

Journal Section

Research Article

Authors

Eda Mercan This is me

Barış Eran This is me

Publication Date

September 30, 2018

Submission Date

November 9, 2017

Acceptance Date

July 21, 2018

Published in Issue

Year 2018 Volume: 39 Number: 3

DOI

https://doi.org/10.17776/csj.350308

IZ

https://izlik.org/JA72NP22CH

Cite

RIS / Bibtex
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
AMA
1.Berkil Akar K, Mercan E, Eran B, Çadırcı BH. Synthesis and Biological Evaluation of Novel 5,8-Dibromo-2-N-substituted-1,4-Naphthoquinone Derivatives as Potential Antimicrobial Agents. CSJ. 2018;39(3):608-614. doi:10.17776/csj.350308
Chicago
Berkil Akar, Kıymet, Eda Mercan, Barış Eran, and Bilge Hilal Çadırcı. 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): 608-14. https://doi.org/10.17776/csj.350308.
EndNote
Berkil Akar K, Mercan E, Eran B, Çadırcı BH (September 1, 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.
IEEE
[1]K. Berkil Akar, E. Mercan, B. Eran, and B. H. Çadırcı, “Synthesis and Biological Evaluation of Novel 5,8-Dibromo-2-N-substituted-1,4-Naphthoquinone Derivatives as Potential Antimicrobial Agents”, CSJ, vol. 39, no. 3, pp. 608–614, Sept. 2018, doi: 10.17776/csj.350308.
ISNAD
Berkil Akar, Kıymet - Mercan, Eda - Eran, Barış - Çadırcı, Bilge Hilal. “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 (September 1, 2018): 608-614. https://doi.org/10.17776/csj.350308.
JAMA
1.Berkil Akar K, Mercan E, Eran B, Çadırcı BH. Synthesis and Biological Evaluation of Novel 5,8-Dibromo-2-N-substituted-1,4-Naphthoquinone Derivatives as Potential Antimicrobial Agents. CSJ. 2018;39:608–614.
MLA
Berkil Akar, Kıymet, et al. “Synthesis and Biological Evaluation of Novel 5,8-Dibromo-2-N-Substituted-1,4-Naphthoquinone Derivatives As Potential Antimicrobial Agents”. Cumhuriyet Science Journal, vol. 39, no. 3, Sept. 2018, pp. 608-14, doi:10.17776/csj.350308.
Vancouver
1.Kıymet Berkil Akar, Eda Mercan, Barış Eran, Bilge Hilal Çadırcı. Synthesis and Biological Evaluation of Novel 5,8-Dibromo-2-N-substituted-1,4-Naphthoquinone Derivatives as Potential Antimicrobial Agents. CSJ. 2018 Sep. 1;39(3):608-14. doi:10.17776/csj.350308

As of 2026, Cumhuriyet Science Journal will be published in six issues per year, released in February, April, June, August, October, and December