Synthesis, anticancer for prostate cancer cells and antibacterial activity of new diazepine derivatives

Fahad, Nahla Ghaze; Imran, Noor H.; Kyhoiesh, Hussein Ali Kadhim; Al-Hussainawy, Mohammed K.

doi:10.1016/j.rechem.2023.101049

Cited by 15 publications

(3 citation statements)

References 35 publications

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“…The study in this area reinforces the conclusion about the structure and nature of bonding discussion in the FTIR spectra. Figures S3a and S3b represent the 1 H NMR spectra for the free ligand (DMPDE) and its Ag(I) complex in DMSO‐d 6 , using TMS as an internal standard [55] . The free ligand (DMPDE) displayed a singlet signal for OH proton in its aromatic moiety in the region of (15.39 and 14.89 ppm) respectively.…”

Section: Resultsmentioning

confidence: 99%

“…Figures S3a and S3b represent the 1 H NMR spectra for the free ligand (DMPDE) and its Ag(I) complex in DMSO-d 6 , using TMS as an internal standard. [55] The free ligand (DMPDE) displayed a singlet signal for OH proton in its aromatic moiety in the region of (15.39 and 14.89 ppm) respectively. It is well known that the OH proton appears in lower fields when hydrogen-bonded.…”

Section: H Nmr Spectramentioning

confidence: 99%

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Synthesis, Characterization, in silico DFT, Molecular docking, ADMET Profiling Studies and Toxicity Predictions of Ag(I) Complex Derived from 4‐Aminoacetophenone

Kyhoiesh,

Hassan

2024

ChemistrySelect

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The reaction of the synthesized (E)‐1‐(4‐((2,4‐dihydroxy‐6‐methylphenyl)diazenyl)phenyl)ethan‐1‐one, (DMPDE) ligand with Ag(I) ion at room temperature resulted in the formation of the complex; [Ag(DMPDE)(H2O)2]. 1H NMR, 13C NMR, FTIR, UV‐Vis, mass spectra, elemental analyses, thermal analysis (TGA/DTA), and molar conductance measurements were done to elucidate the structure of synthetic compounds. The results revealed an interesting geometrical variation; tetrahedral for Ag(I) complex. FT‐IR spectra demonstrated that the ligand (DMPDE) under investigation behaves as a bidentate ligand (N,O) through the nitrogen atom of the azo group which is the farthest of the acetophenone moiety and oxygen phenolic for benzene moiety and forms a stable five‐membered chelating ring. The electronic structure, molecular electrostatic potential (MEP) and quantum chemical calculations of the newly synthesized compounds are investigated theoretically at the DFT/B3LYP level of theory. Additionally, the ligand (DMPDE) and Ag(I) complex were screened against the growth of pathogenic bacteria [Actinomycosis (G+), E. Escherichia Coli (G−)] and fungi (Penicillium spp.) compared with the reference antibiotics, Chloramphenicol and Nystatin. Furthermore, 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) was used to evaluate the antioxidant activities of the ligand and its complex, which showed they both possess significant antioxidant properties in comparison with L‐ascorbic acid (Vit. C) as standard. Based on docking studies, (DMPDE) and Ag(I) complex demonstrated a greater affinity for (PDB ID: 3T88), which corresponds to Escherichia coli protein (−6.7818 kcal/mol) and (−6.7928 kcal/mol), respectively. Interestingly, the most active Ag(I) complex inside the active site of cervical cancer receptor (PDB ID: 4XR8) demonstrated a higher binding energy (−6.2631 kcal/mol) than free ligand (−5.8561 kcal/mol). In silico, ADMET displayed that compounds obey the Lipinski rule and the “Veber's rule. Consequently, is likely to exhibit oral bioavailability with good LD50 and a safety profile that includes non‐cytotoxicity, non‐immunotoxicity, and non‐skin sensitization. Finally, the compounds synthesized showed significant anticancer activity in human cervical cancer cell lines HeLa and SiHa compared with positive controls (cisplatin) and normal human hepatic cells (WRL‐68). In the present study, all tested cancer cell lines showed promising activity against Ag(I) complex, whose IC50 value ranged from (61.02 to 71.09) μg/mL.

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Section: Resultsmentioning

confidence: 99%

Section: H Nmr Spectramentioning

confidence: 99%

Synthesis, Characterization, in silico DFT, Molecular docking, ADMET Profiling Studies and Toxicity Predictions of Ag(I) Complex Derived from 4‐Aminoacetophenone

Kyhoiesh,

Hassan

2024

ChemistrySelect

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“…Tri-cyclic seven-membered imines/amines have emerged as privileged scaffolds in synthetic chemistry, [1] medicinal chemistry, [2] and materials science. [3] In this context, dibenzo-[b,f]azepine, dihydrodibenzo[b,f][1,4]oxazepine, and dihydrodibenzo[b,f][1,4]thiazepine derivatives possess a wide range of biological activities, such as anti-HIV, [4] antidepressant, [5] anticancer, [6] antimicrobial, [7] antiinflammatory, [8] antihistaminic, [9] anticonvulsants, [10] antiplatelet, [11] antinociceptive, [12] and antipsychotic. [13] They are present in various marketed tri-, and tetracyclic drugs, as well as drug candidates (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Recent Progress in Transformations of Azepine/Oxazepine/Thiazepine Derivatives

Doraghi,

Ameli,

Karimian

et al. 2024

ChemistrySelect

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Dibenzoazepine, dibenzoxazepine and dibenzothiazepine scaffolds are an important class of N‐heterocycles that possess multiple biological activities. Due to the widespread application of these motifs in drug discovery, the synthesis of tri‐cyclic seven‐membered imines/amines has gained huge attention of chemists. In the present review, we have highlighted recent advances in functionalization and cyclization reactions of these valuable organic compounds over the last six years.

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Synthesis, Structural Determination, DFT Calculation and Biological Evaluation Supported by Molecular Docking Approach of Some New Complexes Incorporating (E)‐N'‐(3,5‐di‐Tert‐Butyl‐2‐Hydroxybenzylidene) Isonicotino Hydrazide Ligand

Al‐Farraj,

Qasem,

Aouad

et al. 2024

Applied Organom Chemis

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The synthesis and structural analysis of complexes derived from (E)‐N′‐(3,5‐di‐tert‐butyl‐2‐hydroxybenzylidene) isonicotino hydrazide (ITB ligand) were examined using multiple analytical techniques. These techniques included TGA, decomposition point determination, elemental analysis (CHN), spectroscopic (IR, NMR, mass spectrometry) analysis, magnetic susceptibility, conductivity, as well UV–Vis spectrum analysis, along with theoretical studies. Molar conductance values indicated that the Cd (II), Co (II), Cu (II), Ni (II), and Zn (II) complexes are non‐electrolytes in fresh DMSO solutions, with conductance values ranging from 8.5 to 14.35 Ω−1 cm2 mol−1. IR spectra suggested which the ligand coordinates through the metal ions in a tridentate fashion, utilizing the (N & O) donor sites from the (CN & CO & CO) groups in the hydroxybenzylidene moiety. Analytical data from solution complexation, job's method suggested a 1:1 (metal:ligand) molar ratio. The stability order of the complexes was determined as ITBCo > ITBCu > ITBNi > ITBZn > ITBCd, consistent with the stability constant (Kf) values. The pH profile indicated that the studied complexes exhibit stability upon a wide pH scale, typically between (pH = 4:10). Magnetic and electronic spectral analyses helped deduce the ligand coordination abilities and the geometric structures of the complexes. In vitro (antimicrobial & anticancer) performances of the studied complexes were tested versus various (microbial strains & cancer cell lines), revealing higher activity in the chelates assessed to the free (ITB) ligand. The antioxidant potential was also assessed using the DPPH assay. Finally, molecular docking was performed toward estimate the binding efficiency between various protein receptors and the compounds, with results aligning with the biological investigations.

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Synthesis, anticancer for prostate cancer cells and antibacterial activity of new diazepine derivatives

Cited by 15 publications

References 35 publications

Synthesis, Characterization, in silico DFT, Molecular docking, ADMET Profiling Studies and Toxicity Predictions of Ag(I) Complex Derived from 4‐Aminoacetophenone

Synthesis, Characterization, in silico DFT, Molecular docking, ADMET Profiling Studies and Toxicity Predictions of Ag(I) Complex Derived from 4‐Aminoacetophenone

Recent Progress in Transformations of Azepine/Oxazepine/Thiazepine Derivatives

Synthesis, Structural Determination, DFT Calculation and Biological Evaluation Supported by Molecular Docking Approach of Some New Complexes Incorporating (E)‐N'‐(3,5‐di‐Tert‐Butyl‐2‐Hydroxybenzylidene) Isonicotino Hydrazide Ligand

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