Design, synthesis, DFT calculations, molecular docking and antimicrobial activities of novel cobalt, chromium metal complexes of heterocyclic moiety-based 1,3,4-oxadiazole derivatives

Rohand, Taoufik; Ayouchia, Hicham Ben El; Achtak, Hafid; Ghaleb, Adib; Derin, Yavuz; Tutar, Ahmet; Toko, Kiyoshi

doi:10.1080/07391102.2021.1965031

Cited by 5 publications

(3 citation statements)

References 49 publications

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“…Heterocyclic compounds play a pivotal role in synthetic organic chemistry, material science, and pharmaceutical chemistry. [ 1–5 ] Compounds featuring fused quinoline, tetrahydroquinoline, and tetrahydroacridine motifs are particularly significant in the quest for new promising drugs. [ 6–12 ] Tacrine (9‐amino‐1,2,3,4‐tetrahydroacridine), a heterocyclic compound containing a 1,2,3,4‐tetrahydroacridine ring with an amino group, was the first drug approved by the US Food and Drug Administration for treating Alzheimer's disease.…”

Section: Introductionmentioning

confidence: 99%

Novel diarylated tacrine derivatives: Synthesis, characterization, anticancer, antiepileptic, antibacterial, and antifungal activities

Mısır,

Derin,

Ökten

et al. 2024

J Biochem & Molecular Tox

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In this study, our goal was to synthesize novel aryl tacrine derivatives and assess their potential as anticancer, antibacterial agents, and enzyme inhibitors. We adopted a two‐step approach, initiating with the synthesis of dibromotacrine derivatives 3 and 4 through the Friedlander reaction. These intermediates underwent further transformation into diarylated tacrine derivatives 3a–e and 4a–e using a Suzuki–Miyaura cross‐coupling reaction. Thorough characterization of these novel diarylated tacrines was achieved using various spectroscopic techniques. Our findings highlighted the potent anticancer effects of these innovative compounds across a range of cancer cell lines, including lung, gynecologic, bone, colon, and breast cancers, while demonstrating low cytotoxicity against normal cells. Notably, these compounds surpassed the control drug, 5‐Fluorouracil, in terms of antiproliferative activity in numerous cancer cell lines. Moreover, our investigation included an analysis of the inhibitory properties of these novel compounds against various microorganisms and cytosolic carbonic anhydrase enzymes. The results suggest their potential for further exploration as cancer‐specific, enzyme inhibitory, and antibacterial therapeutic agents. Notably, four compounds, namely, 5,7‐bis(4‐(methylthio)phenyl)tacrine (3d), 5,7‐bis(4‐(trifluoromethoxy)phenyl)tacrine (3e), 2,4‐bis(4‐(trifluoromethoxy)phenyl)‐7,8,9,10‐tetrahydro‐6H‐cyclohepta[b]quinolin‐11‐amine (4e), and 6,8‐dibromotacrine (3), emerged as the most promising candidates for preclinical studies.

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Section: Introductionmentioning

confidence: 99%

Novel diarylated tacrine derivatives: Synthesis, characterization, anticancer, antiepileptic, antibacterial, and antifungal activities

Mısır,

Derin,

Ökten

et al. 2024

J Biochem & Molecular Tox

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“…4 Similarly, the cobalt and chromium complexes have also been shown to inhibit FabH activity. 5 (E)-2-((2,3-dihydrobenzo [b][1,4]dioxin-6-yl)methylene)-N-phenylhydrazinecarbothioamide (L) is a poten-tial antibacterial agent that belongs to the class of hydrazinecarbothioamide derivatives. It contains a dioxin ring system, a phenyl group, and a hydrazinecarbothioamide functional group, which are known to possess antibacterial activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structures and Antibacterial Activity of Nickel(II) and Copper(II) Complexes Derived from (E)-2-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methylene)- N-phenylhydrazinecarbothioamide

Wang,

Fei,

Zhou

et al. 2024

ACSi

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The biosynthesis of fatty acids is essential for the survival of bacteria, and β-ketoacyl-acyl carrier protein synthase III (FabH) is a promising target for antibacterial drug development. Nickel(II) complex [NiL2] (1) and copper(II) complex [CuL2] (2), where L is (E)-2-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methylene)-N-phenylhydrazinecarbothioamide, were synthesized and characterized by elemental analysis, IR and 1H NMR spectroscopy and HRMS. Structures of the complexes were further studied by single crystal X-ray determination, which reveals that the nickel and copper atoms in the complexes are in tetrahedral geometry. These compounds were evaluated for their antibacterial and E. coli FabH inhibitory activities.

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“…Metal complexes' pharmacological activity is determined by the coordination of metal ions and ligands [ 24 – 26 ]. Rohand et al [ 27 ] reported that the antimicrobial activity in vitro reveals that metal complexation increases the complexed ligand's antibacterial activity versus both bacterial strains compared to the free ligand (Complexes' higher activity could be attributed to their increased lipophilicity due to their chelation [ 28 ]. Although cisplatin and its derivatives have been widely utilized to treat certain malignancies, their therapeutic efficacy is limited by systemic toxicity and resistance [ 29 – 32 ].…”

Section: Introductionmentioning

confidence: 99%

Study of novel bidentate heterocyclic amine-based metal complexes and their biological activities: cytotoxicity and antimicrobial activity evaluation

et al. 2023

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Metallic antitumor drugs with heterocyclic ligands, such as novel AMI (amino methyl imidazole) complexes [Pd(AMI)Cl2](1), [Cu(AMI)L1](2), and [Cu(AMI)L2·2H2O](3) where L1 = oxalate and L2 = malonate, were synthesized and characterized. Assessments included elemental analyses, mass spectrometry, Fourier transform-infrared spectroscopy, ultraviolet–visible spectroscopy, and thermal analysis. The cytotoxicity of AMI complexes compared to cisplatin was assessed using MTT (3-[4,5-dimethylthiazol-2-yl] 2,5diphenyl tetrazolium bromide) assay with breast (MCF-7) and cervical (HeLa) cancer cell lines. After treating these cells with the AMI complexes' IC50 values for 48 h, malondialdehyde levels and catalase activity were used to assess oxidative stress, antioxidant activity was evaluated with DPPH radical scavenging method, comet assays assessed DNA damage, and DNA fragmentation was evaluated using the gel electrophoresis. In vitro, antimicrobial activity was assessed using a disc diffusion method. The anticancer activity results showed that IC50 (half-maximal inhibitory concentration) values of complex one, two, and three against MCF-7 and HeLa cancer cells are 0.156 ± 0.0006, 0.125 ± 0.001, 0.277 ± 0.002 μM respectively for MCF-7 cells and 0.222 ± 0.0005, 0.126 ± 0.0009, 0.152 ± 0.001 μM respectively for HeLa cells. Complex two demonstrated strong anticancer activity against MCF-7 and Hela cells. The study of oxidative stress parameters revealed that Malondialdehyde levels increased in cancer cell lines treated with complexes compared to untreated cells. Catalase activity decreased in cells treated with palladium chelate. The DPPH radical scavenging assay results identified that complex one was a more potent antioxidant in MCF-7 and Hela cells than other complexes with SC50 values of 227.5 ± 0.28 and 361 ± 1.2 μL/mL, respectively. The comet assay results showed that complex two caused significant DNA damage in MCF-7 and HeLa cancer cells treated. Antimicrobial assays identified complex three as the most effective. Copper complexes give better antifungal activity against A. flavus than the palladium complex. We conclude that complex two is the most active in both cell types and might be assessed as a clinically useful drug for breast cancer treatment. The significance of the current study is the synthesis of antitumor drugs containing heterocyclic ligands, such as novel AMI complexes, and the study of their biological activities.

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Design, synthesis, DFT calculations, molecular docking and antimicrobial activities of novel cobalt, chromium metal complexes of heterocyclic moiety-based 1,3,4-oxadiazole derivatives

Cited by 5 publications

References 49 publications

Novel diarylated tacrine derivatives: Synthesis, characterization, anticancer, antiepileptic, antibacterial, and antifungal activities

Novel diarylated tacrine derivatives: Synthesis, characterization, anticancer, antiepileptic, antibacterial, and antifungal activities

Synthesis, Crystal Structures and Antibacterial Activity of Nickel(II) and Copper(II) Complexes Derived from (E)-2-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methylene)- N-phenylhydrazinecarbothioamide

Study of novel bidentate heterocyclic amine-based metal complexes and their biological activities: cytotoxicity and antimicrobial activity evaluation

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