TY  - JOUR
T1  - Synthesis and Antimicrobial Evaluation of Novel 5,8-Dibromo-2-O/Ssubstituted-1,4-naphthoquinone Derivatives
TT  - Yeni 5,8-Dibromo-2-O/S-sübstitüe-1,4-naftakinon Türevlerinin Sentezi ve Antimikrobiyal Aktivitelerinin Değerlendirilmesi
AU  - Berkil Akar, Kıymet
AU  - Kılınç, Hasan
PY  - 2018
DA  - August
JF  - Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi
PB  - Afyon Kocatepe Üniversitesi
WT  - DergiPark
SN  - 2149-3367
SP  - 451
EP  - 457
VL  - 18
IS  - 2
LA  - en
AB  - 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.
KW  - 1
KW  - 4-Naphthoquinone
KW  - Nucleophilic
KW  - substitution
KW  - Antimicrobial activity
N2  - 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.
CR  - 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.
CR  - 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.
CR  - Anderson, J.B., 2005. Evolution of antifungal-drug resşstabce: mechanisms and pathogen fitness. Nature Reviews Microbiology, 3, 547-556.
CR  - Andrews, J.M., 2001. Determination of minimum inhibition concentrations, Journal of Antimicrobial Chemotherapy, 48 Suppl. S1, 5-16.
CR  - 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.
CR  - Çakmak, O., Berkil Akar, K. and Kaplan, N., 2012. Functionalization of naphthalene: a novel synthetic route to brominated naphthoquiones. Arkivoc, 50 (4), 274-281.
CR  - 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.
CR  - Sayil, C. and Ibis., C., 2010. Synthesis and Spectral Properties of Novel Thionaphtoquinone Dyes. Bulletin of the Korean Chemical Society, 31 (5), 1233-1236.
CR  - 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.
CR  - 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.
CR  - 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.
UR  - http://dergipark.org.tr/tr/pub/akufemubid/issue//539252
L1  - http://dergipark.org.tr/tr/download/article-file/669698
ER  -