Novel nitrated tetrahydroquinoline and quinoline derivatives: Synthesis, characterization and their biological activities as anticancer and antibiotic agents
Journal of Molecular Structure, cilt.1375, 2026 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 1375
- Basım Tarihi: 2026
- Doi Numarası: 10.1016/j.molstruc.2026.146902
- Dergi Adı: Journal of Molecular Structure
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Chimica, Compendex, INSPEC, Academic Search Ultimate (EBSCO), Engineering Source (EBSCO)
- Anahtar Kelimeler: Anticancer, Cytotoxicity, Nitration, Quinoline, Tetrahydroquinoline
- Yozgat Bozok Üniversitesi Adresli: Evet
Özet
A series of novel nitrated tetrahydroquinoline and quinoline derivatives was synthesized via regioselective nitration of substituted brominated precursors under mild, temperature-controlled acidic conditions. The reactions enabled the selective introduction of nitro groups at the C-5 or C-7 positions, depending on the nature and position of substituents on the quinoline or tetrahydroquinoline ring. The structures and regioselectivity of the synthesized compounds were unequivocally confirmed by various spectral methods.The biological activity of the compounds was assessed using MTT and LDH assays against a panel of human cancer cell lines (lung, brain, breast, and colon) and a normal lung epithelial line (Beas-2B). Most compounds exhibited notable antiproliferative activity, with 3,6,8-tribromo-7-nitroquinoline (5) showing the highest cytotoxicity, particularly against A549 and SH-SY5Y cells (IC50, in the low micromolar range) and good selectivity over normal cells. LDH assays supported these findings by indicating membrane-disruptive effects. Additionally, antimicrobial evaluation by the microdilution method revealed moderate to strong activity for selected derivatives, particularly 5-bromo-8-methoxy-7-nitroquinoline (14), which showed activity against clinically relevant pathogens, including MRSA and VRE, as well as Candida albicans, with MIC values ranging from <28.3 to 904.4 µM.Overall, this work demonstrates an efficient synthetic approach to halogenated nitroquinoline derivatives and identifies promising lead compounds with dual anticancer and antimicrobial potential.