Yeni 5,8-Dibromo-2-O/S-sübstitüe-1,4-naftakinon Türevlerinin Sentezi ve Antimikrobiyal Aktivitelerinin Değerlendirilmesi
2,5,8-Tribromo-l,4-naftokinon’dan (1) nükleofilik sübstitüsyon reaksiyonları ile yeni bromo- ve O/S- sübstitüe-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.
Synthesis and Antimicrobial Evaluation of Novel 5,8-Dibromo-2-O/S- substituted-1,4-naphthoquinone Derivatives
Novel bromo- and O/S-substituted-1,4-naphthoquninones (3a-3i) were synthesized via nucleophilicsubstitution reactions from 2,5,8-tribromo-1,4-naphthoquinone (1). Antimicrobial evaluation of thenewly synthesized derivatives was performed using agar spot method. Compounds 3a, 3b, and 3cexhibited the greatest activity with MIC value of 61,25 μg/mL against P. vulgaris, B. cereus andB.subutilis, and B.cereus, respectively. Results revealed that compound 3c has notable activity againstall tested microorganisms.
___
- 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.