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Synthesis, Characterization, and DFT-Based Electronic and Nonlinear Optical Properties of Methyl 1-(arylsulfonyl)-2-aryl-1H-benzo[d]imidazole-6-carboxylates.

ABSTRACT: Herein, a series of N-1-sulfonyl substituted derivatives of 2-substituted benzimidazoles (2a-2e) were designed and synthesized via structural tailoring of the acceptor part of donor-π-acceptor schemes, and their nonlinear optic (NLO) characteristics were reported. The structures of 2a-2e were investigated and their characterization was accomplished by employing spectroscopic procedures, i.e., UV-vis, FT-IR, and ¹H and ¹³C NMR. Further, a density functional theory (DFT) approach was used to calculate UV-vis, vibrational, and ¹H and ¹³C NMR techniques; frontier molecular orbitals (FMOs); global reactivity parameters (GRPs); natural bond orbitals (NBOs); optical and vibrational analysis; and nonlinear optics (NLO). The most promising results were obtained for 6-nitro-2-(4-nitrophenyl)-1-(4-nitrophenylsulfonyl)-1H-benzo[d]imidazole among entitled compounds, as it exhibited the highest ⟨α⟩ and β_tot values, showing it is an eye-catching NLO material. This DFT study evokes the interest of researchers regarding the development of benzimidazole-based tempting NLO compounds that could be beneficial in modern hi-tech applications.

SUBMITTER: Aslam S

PROVIDER: S-EPMC9453983 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Synthesis, Characterization, and DFT-Based Electronic and Nonlinear Optical Properties of Methyl 1-(arylsulfonyl)-2-aryl-1H-benzo[d]imidazole-6-carboxylates.

Aslam Shumaila S Haroon Muhammad M Akhtar Tashfeen T Arshad Muhammad M Khalid Muhammad M Shafiq Zahid Z Imran Muhammad M Ullah Aman A

ACS omega 20220823 35

Herein, a series of N-1-sulfonyl substituted derivatives of 2-substituted benzimidazoles (2a-2e) were designed and synthesized via structural tailoring of the acceptor part of donor-π-acceptor schemes, and their nonlinear optic (NLO) characteristics were reported. The structures of 2a-2e were investigated and their characterization was accomplished by employing spectroscopic procedures, i.e., UV-vis, FT-IR, and 1H and 13C NMR. Furth ...[more]

PMID: 36092624

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Project description:To identify new candidate anticancer compounds, we here report the synthesis of benzimidazole derivatives: diethyl 2,2'-(2-oxo-1H-benzo[d]imidazole-1,3(2H)-diyl) diacetate and its arylideneacetohydrazide derivatives, using ultrasonic irradiation and conventional heating. The compounds were confirmed by Nuclear magnetic resonance (NMR) (JEOL, Tokyo, Japan) and Fourier transform infrared spectroscopy (FTIR) spectroscopy (Thermoscientific, Waltham, MA, USA). The molecular structure and electronic properties of the studied compounds were predicted for the acetohydrazide hydrazones. These compounds exist as a mixture of configurational and conformational isomerism as well as amido-amidic acid tautomerism. The NMR spectral data proved the predominance of syn-E amido isomers. In addition, density functional theory (DFT) predicted stability in the gas phase and showed that syn-E amido isomers are the most stable in the presence of an electron donating group, while the anti-isomer is the most stable in the presence of electron-attracting substituents. The anticancer activity of these synthetic compounds 6a, 6b and 6c towards both colon cancer (HCT-116) and cervical cancer (HeLa) cells was examined by MTT assay and DAPI staining. The MTT assay revealed a strong antiproliferative effect against the cancer cells at low concentrations, and interestingly, no significant inhibitory action against the non-cancerous cell line, HEK-293. The IC50 values for HCT-116 were 29.5 + 4.53 µM, 57.9 + 7.01 µM and 40.6 + 5.42 µM for 6a, 6b, and 6c, respectively. The IC50 values for HeLa cells were 57.1 + 6.7 µM, 65.6 + 6.63 µM and 33.8 + 3.54 µM for 6a, 6b, and 6c, respectively. DAPI staining revealed that these synthesized benzimidazole derivatives caused apoptotic cell death in both the colon and cervical cancer cells. Thus, these synthetic compounds demonstrate encouraging anticancer activity as well as being safe for normal human cells, making them attractive candidates as anticancer agents.

Dataset Information

Synthesis, Characterization, and DFT-Based Electronic and Nonlinear Optical Properties of Methyl 1-(arylsulfonyl)-2-aryl-1H-benzo[d]imidazole-6-carboxylates.

Publications

Synthesis, Characterization, and DFT-Based Electronic and Nonlinear Optical Properties of Methyl 1-(arylsulfonyl)-2-aryl-1H-benzo[d]imidazole-6-carboxylates.

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