Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents

KOCAGÖZ, Zühtü Tanıl; KARAYEL, Kaan Gökçe; Küçükgüzel, İlkay; TAŞLI, Pakize Neslihan; Sahin, Fikrettin; unubol, Nihan; oktem okullu, sinem; TATAR, Esra; DEMİRCİ, Aslı

doi:10.3906/kim-1710-35

Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents

Aslı DEMİRCİ, (Marmara Üniversitesi, Eczacılık Fakültesi, Farmasötik Kimya Anabilim Dalı, İstanbul, Türkiye)

Kaan Gökçe KARAYEL, (Marmara Üniversitesi, Eczacılık Fakültesi, Farmasötik Kimya Anabilim Dalı, İstanbul, Türkiye)

Esra TATAR, (Marmara Üniversitesi, Eczacılık Fakültesi, Farmasötik Kimya Anabilim Dalı, İstanbul, Türkiye)

Sinem ÖKTEM OKULLU, (Acıbadem Üniversitesi, Tıp Fakültesi,Tıbbi Mikrobiyoloji Anabilim Dalı, İstanbul, Türkiye)

Nihan ÜNÜBOL, (Acıbadem Üniversitesi, Tıp Fakültesi, Tıbbi Mikrobiyoloji Anabilim Dalı, İstanbul, Türkiye)

Pakize Neslihan TAŞLI, (Yeditepe Üniversitesi, Mühendislik Fakültesi, Genetik ve Biyomühendislik Bölümü, İstanbul, Türkiye)

Zühtü Tanıl KOCAGÖZ, (Acıbadem Üniversitesi, Tıp Fakültesi, Tıbbi Mikrobiyoloji Anabilim Dalı, İstanbul, Türkiye)

Fikrettin ŞAHİN, (Yeditepe Üniversitesi, Mühendislik Fakültesi, Genetik ve Biyomühendislik Bölümü, İstanbul, Türkiye)

İlkay KÜÇÜKGÜZEL (Marmara Üniversitesi, Eczacılık Fakültesi, Farmasötik Kimya Anabilim Dalı, İstanbul, Türkiye)

Turkish Journal of Chemistry

2 0

Yıl: 2018 Cilt: 42 Sayı: 3 Sayfa Aralığı: 839 - 858 Metin Dili: İngilizce DOI: 10.3906/kim-1710-35 İndeks Tarihi: 20-12-2020

Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents

Öz:

A series of 5-substituted-1,3,4-thiadiazole-based fluoroquinolone derivatives were designed as potential antibacterial and anticancer agents using a molecular hybridization approach. The target compounds 16–25 were synthesized by reacting the corresponding N -(5-substituted-1,3,4-thiadiazol-2-yl)-2-chloroacetamides with ciprofloxacin ornorfloxacin. The purity and identity of the synthesized compounds were determined by the use of chromatographicand spectral techniques (NMR, IR, MS, etc.) besides elemental analysis. Antibacterial, antituberculosis, and anticancer activity of the target compounds were evaluated against selected strains and cancer cell lines. Compound 20was appreciated as the most active agent representing antibacterial activity against Escherichia coli and Staphylococcusaureus with MIC values of 4 µg/mL and 2 µg/mL, respectively. Amongst the synthesized fluoroquinolone derivatives,compounds 19 and 20 were found to have modest antitubercular activity with 8 µg/mL MIC values for each. Mostpotent derivative, compound 20 was docked against Staphylococcus aureus and Mycobacterium tuberculosis DNA gyraseenzymes to visualize the possible conformation of the compound. Additionally, anticancer activities of target compoundswere evaluated on seven different cancer cell lines.

Anahtar Kelime:

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

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APA	DEMİRCİ A, KARAYEL K, TATAR E, oktem okullu s, unubol N, TAŞLI P, KOCAGÖZ Z, Sahin F, Küçükgüzel İ (2018). Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents. , 839 - 858. 10.3906/kim-1710-35
Chicago	DEMİRCİ Aslı,KARAYEL Kaan Gökçe,TATAR Esra,oktem okullu sinem,unubol Nihan,TAŞLI Pakize Neslihan,KOCAGÖZ Zühtü Tanıl,Sahin Fikrettin,Küçükgüzel İlkay Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents. (2018): 839 - 858. 10.3906/kim-1710-35
MLA	DEMİRCİ Aslı,KARAYEL Kaan Gökçe,TATAR Esra,oktem okullu sinem,unubol Nihan,TAŞLI Pakize Neslihan,KOCAGÖZ Zühtü Tanıl,Sahin Fikrettin,Küçükgüzel İlkay Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents. , 2018, ss.839 - 858. 10.3906/kim-1710-35
AMA	DEMİRCİ A,KARAYEL K,TATAR E,oktem okullu s,unubol N,TAŞLI P,KOCAGÖZ Z,Sahin F,Küçükgüzel İ Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents. . 2018; 839 - 858. 10.3906/kim-1710-35
Vancouver	DEMİRCİ A,KARAYEL K,TATAR E,oktem okullu s,unubol N,TAŞLI P,KOCAGÖZ Z,Sahin F,Küçükgüzel İ Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents. . 2018; 839 - 858. 10.3906/kim-1710-35
IEEE	DEMİRCİ A,KARAYEL K,TATAR E,oktem okullu s,unubol N,TAŞLI P,KOCAGÖZ Z,Sahin F,Küçükgüzel İ "Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents." , ss.839 - 858, 2018. 10.3906/kim-1710-35
ISNAD	DEMİRCİ, Aslı vd. "Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents". (2018), 839-858. https://doi.org/10.3906/kim-1710-35

APA	DEMİRCİ A, KARAYEL K, TATAR E, oktem okullu s, unubol N, TAŞLI P, KOCAGÖZ Z, Sahin F, Küçükgüzel İ (2018). Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents. Turkish Journal of Chemistry, 42(3), 839 - 858. 10.3906/kim-1710-35
Chicago	DEMİRCİ Aslı,KARAYEL Kaan Gökçe,TATAR Esra,oktem okullu sinem,unubol Nihan,TAŞLI Pakize Neslihan,KOCAGÖZ Zühtü Tanıl,Sahin Fikrettin,Küçükgüzel İlkay Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents. Turkish Journal of Chemistry 42, no.3 (2018): 839 - 858. 10.3906/kim-1710-35
MLA	DEMİRCİ Aslı,KARAYEL Kaan Gökçe,TATAR Esra,oktem okullu sinem,unubol Nihan,TAŞLI Pakize Neslihan,KOCAGÖZ Zühtü Tanıl,Sahin Fikrettin,Küçükgüzel İlkay Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents. Turkish Journal of Chemistry, vol.42, no.3, 2018, ss.839 - 858. 10.3906/kim-1710-35
AMA	DEMİRCİ A,KARAYEL K,TATAR E,oktem okullu s,unubol N,TAŞLI P,KOCAGÖZ Z,Sahin F,Küçükgüzel İ Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents. Turkish Journal of Chemistry. 2018; 42(3): 839 - 858. 10.3906/kim-1710-35
Vancouver	DEMİRCİ A,KARAYEL K,TATAR E,oktem okullu s,unubol N,TAŞLI P,KOCAGÖZ Z,Sahin F,Küçükgüzel İ Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents. Turkish Journal of Chemistry. 2018; 42(3): 839 - 858. 10.3906/kim-1710-35
IEEE	DEMİRCİ A,KARAYEL K,TATAR E,oktem okullu s,unubol N,TAŞLI P,KOCAGÖZ Z,Sahin F,Küçükgüzel İ "Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents." Turkish Journal of Chemistry, 42, ss.839 - 858, 2018. 10.3906/kim-1710-35
ISNAD	DEMİRCİ, Aslı vd. "Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents". Turkish Journal of Chemistry 42/3 (2018), 839-858. https://doi.org/10.3906/kim-1710-35