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Synthesis and Antimicrobial Evaluation of Novel 5,8-Dibromo-2-O/Ssubstituted-1,4-naphthoquinone Derivatives

Year 2018, Volume: 18 Issue: 2, 451 - 457, 31.08.2018

Abstract

Novel bromo- and O/S-substituted-1,4-naphthoquninones (3a-3i) were synthesized via nucleophilic substitution reactions from 2,5,8-tribromo-1,4-naphthoquinone (1). Antimicrobial evaluation of the newly synthesized derivatives was performed using agar spot method. Compounds 3a, 3b, and 3c exhibited the greatest activity with MIC value of 61,25 μg/mL against P. vulgaris, B. cereus and B.subutilis, and B.cereus, respectively. Results revealed that compound 3c has notable activity against all tested microorganisms.

References

  • Aeken, S.V., Deblander, J., Houwer, J.D., Mosselmans, T. and Tehrani, K.A., 2011. Unexpected reaction of 2-amino-1,4-naphthoquinone with aldehydes: new synthesis of naphtho[2,1-d]oxazole compounds. Tetrahedron, 67, 512-517.
  • Ambrogi, V., Artini, D., De Carneri, I., Castellino, S., Dradi, E., Logermann, W., Meinardi, G., Di Somma, M. and Tosolini, G., 1970. Studies on the antibacterial and antifungal properties of 1,4-naphthoquinones. British Journal of Pharmacology, 40, 871-880.
  • Anderson, J.B., 2005. Evolution of antifungal-drug resşstabce: mechanisms and pathogen fitness. Nature Reviews Microbiology, 3, 547-556.
  • Andrews, J.M., 2001. Determination of minimum inhibition concentrations, Journal of Antimicrobial Chemotherapy, 48 Suppl. S1, 5-16.
  • Bolognesi, M.L., Lizzi, F., Perozzo, R., Brun, R. and Cavalli, A., 2008. 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. Bioorganic & Medicinal Chemistry Letters, 18, 2272-2276.
  • Çakmak, O., Berkil Akar, K. and Kaplan, N., 2012. Functionalization of naphthalene: a novel synthetic route to brominated naphthoquiones. Arkivoc, 50 (4), 274-281.
  • Lien, J.-C., Huang, L.-J., Wang, J.-P., Teng, C.-M., Lee, K.-H. and Kuo, S.-C., 1997. Synthesis and Antiplatelet, Antiinflammatory, and Antiallergic Activities of 2-substituted 3-Chloro-1,4-naphthoquinone Derivatives. Bioorganic & Medicinal Chemistry, 5 (12), 2111-2120.
  • Sayil, C. and Ibis., C., 2010. Synthesis and Spectral Properties of Novel Thionaphtoquinone Dyes. Bulletin of the Korean Chemical Society, 31 (5), 1233-1236.
  • Tandon, V.K., Chhor, R.B., Singh, R.V., Rai, S. and Yadav, D.B., 2004. Design, synthesis and evaluation of novel 1,4-naphthoquinone derivatives as antifungal and anticancer agents. Bioorganic & Medicinal Chemistry Letters, 14, 1079-1083.
  • Tandon, V.K., Maurya, H.K., Mishra, N.N. and Shukla, P.K., 2009. Design, synthesis and biological evaluation of novel nitrogen and sülfür containing hetero-1,4-naphthoquinones as potent antifungal and antimicrobial agents. European Journal of Medicinal Chemistry, 44, 3130-3137.
  • Wiegand, I., Hilpert, K. and Hancock, R.E.W., 2008. Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances. Nature Protocols, 3/2, 163-175.

Yeni 5,8-Dibromo-2-O/S-sübstitüe-1,4-naftakinon Türevlerinin Sentezi ve Antimikrobiyal Aktivitelerinin Değerlendirilmesi

Year 2018, Volume: 18 Issue: 2, 451 - 457, 31.08.2018

Abstract

2,5,8-Tribromo-l,4-naftokinon’dan (1) nükleofilik sübstitüsyon reaksiyonları ile yeni bromo- ve O/Ssübstitüe-1,4-naftokininon (3a-3i) türevleri sentezlendi. Yeni sentezlenen türevlerin antimikrobiyal olarak incelenmesi agar spot yöntemi kullanılarak gerçekleştirildi. Bileşik 3a, 3b ve 3c sırasıyla P. vulgaris, B. cereus ve B.subutilis, ve B.cereus'a karşı 61,25 ug/mL’lik MIC değeri ile en büyük aktivite sergiledi. Sonuçlar, bileşik 3c'nin test edilen tüm mikroorganizmalara karşı belirgin etkinliğe sahip olduğunu ortaya koymuştur.

References

  • Aeken, S.V., Deblander, J., Houwer, J.D., Mosselmans, T. and Tehrani, K.A., 2011. Unexpected reaction of 2-amino-1,4-naphthoquinone with aldehydes: new synthesis of naphtho[2,1-d]oxazole compounds. Tetrahedron, 67, 512-517.
  • Ambrogi, V., Artini, D., De Carneri, I., Castellino, S., Dradi, E., Logermann, W., Meinardi, G., Di Somma, M. and Tosolini, G., 1970. Studies on the antibacterial and antifungal properties of 1,4-naphthoquinones. British Journal of Pharmacology, 40, 871-880.
  • Anderson, J.B., 2005. Evolution of antifungal-drug resşstabce: mechanisms and pathogen fitness. Nature Reviews Microbiology, 3, 547-556.
  • Andrews, J.M., 2001. Determination of minimum inhibition concentrations, Journal of Antimicrobial Chemotherapy, 48 Suppl. S1, 5-16.
  • Bolognesi, M.L., Lizzi, F., Perozzo, R., Brun, R. and Cavalli, A., 2008. 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. Bioorganic & Medicinal Chemistry Letters, 18, 2272-2276.
  • Çakmak, O., Berkil Akar, K. and Kaplan, N., 2012. Functionalization of naphthalene: a novel synthetic route to brominated naphthoquiones. Arkivoc, 50 (4), 274-281.
  • Lien, J.-C., Huang, L.-J., Wang, J.-P., Teng, C.-M., Lee, K.-H. and Kuo, S.-C., 1997. Synthesis and Antiplatelet, Antiinflammatory, and Antiallergic Activities of 2-substituted 3-Chloro-1,4-naphthoquinone Derivatives. Bioorganic & Medicinal Chemistry, 5 (12), 2111-2120.
  • Sayil, C. and Ibis., C., 2010. Synthesis and Spectral Properties of Novel Thionaphtoquinone Dyes. Bulletin of the Korean Chemical Society, 31 (5), 1233-1236.
  • Tandon, V.K., Chhor, R.B., Singh, R.V., Rai, S. and Yadav, D.B., 2004. Design, synthesis and evaluation of novel 1,4-naphthoquinone derivatives as antifungal and anticancer agents. Bioorganic & Medicinal Chemistry Letters, 14, 1079-1083.
  • Tandon, V.K., Maurya, H.K., Mishra, N.N. and Shukla, P.K., 2009. Design, synthesis and biological evaluation of novel nitrogen and sülfür containing hetero-1,4-naphthoquinones as potent antifungal and antimicrobial agents. European Journal of Medicinal Chemistry, 44, 3130-3137.
  • Wiegand, I., Hilpert, K. and Hancock, R.E.W., 2008. Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances. Nature Protocols, 3/2, 163-175.
There are 11 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Kıymet Berkil Akar

Hasan Kılınç This is me

Publication Date August 31, 2018
Submission Date November 7, 2017
Published in Issue Year 2018 Volume: 18 Issue: 2

Cite

APA Berkil Akar, K., & Kılınç, H. (2018). Synthesis and Antimicrobial Evaluation of Novel 5,8-Dibromo-2-O/Ssubstituted-1,4-naphthoquinone Derivatives. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, 18(2), 451-457.
AMA Berkil Akar K, Kılınç H. Synthesis and Antimicrobial Evaluation of Novel 5,8-Dibromo-2-O/Ssubstituted-1,4-naphthoquinone Derivatives. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. August 2018;18(2):451-457.
Chicago Berkil Akar, Kıymet, and Hasan Kılınç. “Synthesis and Antimicrobial Evaluation of Novel 5,8-Dibromo-2-O/Ssubstituted-1,4-Naphthoquinone Derivatives”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 18, no. 2 (August 2018): 451-57.
EndNote Berkil Akar K, Kılınç H (August 1, 2018) Synthesis and Antimicrobial Evaluation of Novel 5,8-Dibromo-2-O/Ssubstituted-1,4-naphthoquinone Derivatives. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 18 2 451–457.
IEEE K. Berkil Akar and H. Kılınç, “Synthesis and Antimicrobial Evaluation of Novel 5,8-Dibromo-2-O/Ssubstituted-1,4-naphthoquinone Derivatives”, Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, vol. 18, no. 2, pp. 451–457, 2018.
ISNAD Berkil Akar, Kıymet - Kılınç, Hasan. “Synthesis and Antimicrobial Evaluation of Novel 5,8-Dibromo-2-O/Ssubstituted-1,4-Naphthoquinone Derivatives”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 18/2 (August 2018), 451-457.
JAMA Berkil Akar K, Kılınç H. Synthesis and Antimicrobial Evaluation of Novel 5,8-Dibromo-2-O/Ssubstituted-1,4-naphthoquinone Derivatives. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2018;18:451–457.
MLA Berkil Akar, Kıymet and Hasan Kılınç. “Synthesis and Antimicrobial Evaluation of Novel 5,8-Dibromo-2-O/Ssubstituted-1,4-Naphthoquinone Derivatives”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, vol. 18, no. 2, 2018, pp. 451-7.
Vancouver Berkil Akar K, Kılınç H. Synthesis and Antimicrobial Evaluation of Novel 5,8-Dibromo-2-O/Ssubstituted-1,4-naphthoquinone Derivatives. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2018;18(2):451-7.