Hybrid Quinoline-Sulfonamide Complexes (M2+) Derivatives with Antimicrobial Activity

Abstract

Two new series of hybrid quinoline-sulfonamide complexes (M2+: Zn2+, Cu2+, Co2+ and Cd2+) derivatives (QSC) were designed, synthesized and tested for their antimicrobial activity. The synthesis is straightforward and efficient, involving two steps: acylation of aminoquinoline followed by complexation with metal acetate (Cu2+, Co2+ and Cd2+) or chloride (Zn2+). The synthesized QSC compounds were characterized by FTIR and NMR spectroscopy and by X-ray diffraction on single crystal. The QSC compounds were preliminary screened for their antibacterial and antifungal activity and the obtained results are very promising. In this respect, the hybrid N-(quinolin-8-yl)-4-chloro-benzenesulfonamide cadmium (II), considered as leading structure for further studies, has an excellent antibacterial activity against Staphylococcus aureus ATCC25923 (with a diameters of inhibition zones of 21 mm and a minimum inhibitory concentration (MIC) of 19.04 × 10−5 mg/mL), a very good antibacterial activity against Escherichia coli ATCC25922 (with a diameters of inhibition zones of 19 mm and a MIC of 609 × 10−5 mg/mL), and again an excellent antifungal activity against Candida albicans ATCC10231 (with a diameters of inhibition zones of 25 mm and a MIC of 19.04 × 10−5 mg/mL).

Benzoquinoline Derivatives: A Straightforward and Efficient Route to Antibacterial and Antifungal Agents

“…tifungal, anti-HIV, anticancer, antinociceptive and anti-inflammatory, antipsychotic, algesic, anti-Alzheimer's, antihypertensive properties, etc. [5][6][7][8][9][10][11][12][13][14][15][16][17]. Moreover, the quinol pharmacophore has proved to be one of the most effective motifs used in antibacterial a antifungal therapy, and many of the existing drugs on the market incorporate a quinol scaffold e.g., ciprofloxacin (antibacterial), bedaquiline (antitubercular), etc.…”

“…Because the antimicrobial activity of the obtained cycloaddu PBQC 4e and 4g, was negligible, we did not continue our studies in this direction. The structures of compounds were proved by elemental and spectral analysis (FT-1 H-NMR, 13 C-NMR, and two-dimensional experiments 2D-COSY, HMQC, HMBC). T main data furnished by FT-IR and NMR spectral analysis are listed in Table 1.…”

“…Quinoline and its benzo-fused derivative, benzoquinoline, are crucial scaffolds in medicinal chemistry and they have been reported to possess a large variety of biological activities which include antiplasmodial and antimalarial, antitubercular, antibacterial, antifungal, anti-HIV, anticancer, antinociceptive and anti-inflammatory, antipsychotic, analgesic, anti-Alzheimer’s, antihypertensive properties, etc. [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 ]. Moreover, the quinoline pharmacophore has proved to be one of the most effective motifs used in antibacterial and antifungal therapy, and many of the existing drugs on the market incorporate a quinoline scaffold e.g., ciprofloxacin (antibacterial), bedaquiline (antitubercular), etc.…”

“…Taking into consideration the above considerations and our expertise in the field of antibacterial and antifungal agents [ 13 , 15 , 20 , 21 , 22 , 23 , 24 , 25 ], we report here the design, synthesis, molecular docking, antibacterial and antifungal evaluation of some new benzo[f]quinoline derivatives.…”

Folic acid-sulfonamide conjugates as antibacterial agents: design, synthesis and molecular docking studies

“…These are structurally similar to p-aminobenzoic acid (PABA), so as an analog of PABA, sulfonamides can compete with it efficiently to prevent the synthesis of proteins and nucleic acid which results in the inhibition of various microorganisms. [5][6][7][8] Moreover, a sulfonamide is a versatile moiety owing to its diverse pharmacological activities from antimicrobial to anticancer activities [9][10][11][12][13][14][15][16] and its enzyme inhibition, such as cyclooxygenase, carbonic anhydrase, urease, acetylcholinesterase, butyrylcholinesterase, dihydropteroate synthase and DHFR. [17][18][19][20][21][22][23][24][25] Sulfonamides play a vital role as antibiotics, anti-malarial agents, protease inhibitors, antiretroviral agents in the treatment of HIV/AIDS, and for treating asthma, leukemia and epilepsy.…”