Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents

ARSLAN, TAYFUN; KÜÇÜK, MURAT; TOSUN, Gonca; YAYLI, Nurettin; Alpay Karaoğlu, Şengül; İSKEFİYELİ, Zeynep

Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents

Gonca TOSUN, (Bilim Kimya Bölümü, Mühendislik Fakültesi, Karadeniz Teknik Üniversitesi, Trabzon, Türkiye)

Tayfun ARSLAN, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Giresun, Türkiye)

Zeynep İSKEFİYELİ, (Bilim Kimya Bölümü, Mühendislik Fakültesi, Karadeniz Teknik Üniversitesi, Trabzon, Türkiye)

Murat KÜÇÜK, (Bilim Kimya Bölümü, Mühendislik Fakültesi, Karadeniz Teknik Üniversitesi, Trabzon, Türkiye)

ŞENGÜL ALPAY KARAOĞLU, (Recep Tayyip Erdoğan Üniversitesi, Fen Fakültesi, Biyoloji Bölümü, Rize, Türkiye)

Nurettin YAYLI (Karadeniz Teknik Üniversitesi , Eczacılık Fakültesi, Trabzon, Türkiye)

Turkish Journal of Chemistry

1 0

Yıl: 2015 Cilt: 39 Sayı: 4 Sayfa Aralığı: 850 - 866 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents

Öz:

Three new series of 33 quinolone compounds, 2-(2-, 3-, and 4-fluorophenyl)-4-O-alkyl(C5−15) quinolines (7ak, 8a k, and 9a k), were synthesized from 2-(2-, 3-, and 4-fluorophenyl)-2,3-dihydroquinolin-4(1H )-one (4, 5, and 6) by the reaction of alkyl halides under basic conditions in DMF. The new compounds 7a k, 8a k, and 9a k were synthesized from flavonones 4 6, which can be considered new precursors for quinoline synthesis through a one-step reaction. All the target compounds (7a k, 8a k, and 9a k) were evaluated for their in vitro antimicrobial activity against nine test microorganisms. They showed the most activity against Mycobacterium smegmatis with minimum inhibitory concentrations (MIC) of 62.5 500 µg/mL, indicating their potential uses as antituberculosis agents. Among them 8a k (m-fluoride) were the most active compounds against M. smegmatis (MIC, 62.5 125 µg/mL). The newly synthesized title compounds were also evaluated for their in vitro antioxidant activities using DPPH radical scavenging and FRAP tests. They showed at a low concentration (mg/mL) a range of SC50 values of 0.03 12.48 mg/mL (DPPH ) and 0 722 µM (FRAP), respectively. The antioxidant results of compounds 7a k, 8a k, and 9a k revealed that the length of the alkyl chain was negatively correlated with antioxidant capacity.

Anahtar Kelime:

Konular: Mühendislik, Kimya

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

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APA	TOSUN G, ARSLAN T, İSKEFİYELİ Z, KÜÇÜK M, Alpay Karaoğlu Ş, YAYLI N (2015). Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents. , 850 - 866.
Chicago	TOSUN Gonca,ARSLAN TAYFUN,İSKEFİYELİ Zeynep,KÜÇÜK MURAT,Alpay Karaoğlu Şengül,YAYLI Nurettin Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents. (2015): 850 - 866.
MLA	TOSUN Gonca,ARSLAN TAYFUN,İSKEFİYELİ Zeynep,KÜÇÜK MURAT,Alpay Karaoğlu Şengül,YAYLI Nurettin Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents. , 2015, ss.850 - 866.
AMA	TOSUN G,ARSLAN T,İSKEFİYELİ Z,KÜÇÜK M,Alpay Karaoğlu Ş,YAYLI N Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents. . 2015; 850 - 866.
Vancouver	TOSUN G,ARSLAN T,İSKEFİYELİ Z,KÜÇÜK M,Alpay Karaoğlu Ş,YAYLI N Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents. . 2015; 850 - 866.
IEEE	TOSUN G,ARSLAN T,İSKEFİYELİ Z,KÜÇÜK M,Alpay Karaoğlu Ş,YAYLI N "Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents." , ss.850 - 866, 2015.
ISNAD	TOSUN, Gonca vd. "Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents". (2015), 850-866.

APA	TOSUN G, ARSLAN T, İSKEFİYELİ Z, KÜÇÜK M, Alpay Karaoğlu Ş, YAYLI N (2015). Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents. Turkish Journal of Chemistry, 39(4), 850 - 866.
Chicago	TOSUN Gonca,ARSLAN TAYFUN,İSKEFİYELİ Zeynep,KÜÇÜK MURAT,Alpay Karaoğlu Şengül,YAYLI Nurettin Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents. Turkish Journal of Chemistry 39, no.4 (2015): 850 - 866.
MLA	TOSUN Gonca,ARSLAN TAYFUN,İSKEFİYELİ Zeynep,KÜÇÜK MURAT,Alpay Karaoğlu Şengül,YAYLI Nurettin Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents. Turkish Journal of Chemistry, vol.39, no.4, 2015, ss.850 - 866.
AMA	TOSUN G,ARSLAN T,İSKEFİYELİ Z,KÜÇÜK M,Alpay Karaoğlu Ş,YAYLI N Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents. Turkish Journal of Chemistry. 2015; 39(4): 850 - 866.
Vancouver	TOSUN G,ARSLAN T,İSKEFİYELİ Z,KÜÇÜK M,Alpay Karaoğlu Ş,YAYLI N Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents. Turkish Journal of Chemistry. 2015; 39(4): 850 - 866.
IEEE	TOSUN G,ARSLAN T,İSKEFİYELİ Z,KÜÇÜK M,Alpay Karaoğlu Ş,YAYLI N "Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents." Turkish Journal of Chemistry, 39, ss.850 - 866, 2015.
ISNAD	TOSUN, Gonca vd. "Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents". Turkish Journal of Chemistry 39/4 (2015), 850-866.