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

Yıl 2018, Cilt: 18 Sayı: 2, 451 - 457, 31.08.2018

Öz

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.

Kaynakça

  • 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

Yıl 2018, Cilt: 18 Sayı: 2, 451 - 457, 31.08.2018

Öz

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.

Kaynakça

  • 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.
Toplam 11 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Mühendislik
Bölüm Makaleler
Yazarlar

Kıymet Berkil Akar

Hasan Kılınç Bu kişi benim

Yayımlanma Tarihi 31 Ağustos 2018
Gönderilme Tarihi 7 Kasım 2017
Yayımlandığı Sayı Yıl 2018 Cilt: 18 Sayı: 2

Kaynak Göster

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. Ağustos 2018;18(2):451-457.
Chicago Berkil Akar, Kıymet, ve 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, sy. 2 (Ağustos 2018): 451-57.
EndNote Berkil Akar K, Kılınç H (01 Ağustos 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 ve 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, c. 18, sy. 2, ss. 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 (Ağustos 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 ve 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, c. 18, sy. 2, 2018, ss. 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.