Quantum computational, Spectroscopic investigations on benzofuranylcarbonylpyrazolopyridine by DFT/TD-DFT: Synthesis, Structure, NBO and NLO research

Halim, Shimaa Abdel; Ibrahim, Magdy A.

doi:10.1016/j.molstruc.2023.136201

Cited by 9 publications

(1 citation statement)

References 39 publications

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“…Khellin, a photochemotherapeutic, is frequently used to treat vitiligo and psoriasis, as well as skin diseases [14,15]. Furo [3,2-g]chromenes have been examined for their solvatochromic, electronic and photoelectrical characteristics, as well as theoretical DFT calculations [16,17]. A wide range of furo[3,2-g]chromenes and benzofurans have been synthesized using khellin containing electron-withdrawing substituents at position 6 [18,19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antimicrobial and Anticancer Evaluations of Some Novel Heteroannulated Difuro[3,2-c:3′,2′-g]Chromenes

Alshaye,

Ibrahim,

Badran

2024

Molecules

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The goal of this study was directed to synthesize a novel class of annulated compounds containing difuro[3,2-c:3′,2′-g]chromene. Friedländer condensation of o-aminoacetyl derivative 3 was performed with some active methylene ketones, namely, 1,3-cyclohexanediones, pyrazolones, 1,3-thiazolidinones and barbituric acids, furnished furochromenofuroquinolines (4,5), furochromenofuropyrazolopyridines (6–8), furochromenofurothiazolopyridines (9,10) and furochromenofuropyridopyrimidines (11, 12), respectively. Also, condensation of substrate 3 with 5-amine-3-methyl-1H-pyrazole and 6-amino-1,3-dimethyluracil, as cyclic enamines, resulted in polyfused systems 13 and 14, respectively. In vitro antimicrobial efficiency of the prepared heterocycles against microbial strains exhibited variable inhibition action, where compound 3 was the most effective against all kinds of microorganisms. A significant cytotoxic activity was seen upon the annulation of the starting compound with thiazolopyridine (9 and 10) as well as pyridopyrimidine moieties (11, 12 and 14). The spectroscopic and analytical results were used to infer the structures of the novel synthesized compounds.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antimicrobial and Anticancer Evaluations of Some Novel Heteroannulated Difuro[3,2-c:3′,2′-g]Chromenes

Alshaye,

Ibrahim,

Badran

2024

Molecules

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Recyclization of 3‐substituted‐6,8‐dimethylchromones with some heterocyclic enamines: Spectroscopic, quantum calculations (HOMO–LUMO, MEP, NLO), biological evaluation, and ADME investigation

Badran,

Ibrahim

2024

Journal of Heterocyclic Chem

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The chemical reactivity of some 6,8‐dimethylchromones was studied toward certain heterocyclic enamines. Treatment of carboxaldehyde 1a with the certain enamines proceeded via condensation with concomitant γ‐pyrone ring opening. Reaction of carbonitrile 1b with enamine derivatives proceeded through opening of γ‐pyrone moiety associated with cycloaddition into the nitrile function. A novel angular chromenopyrazolopyridine and chromenopyridopyrimidines were efficiently synthesized from reacting carboxamide 1c with the current enamines. Moreover, frontier molecular orbitals analysis, electronegativity, global hardness, global softness, ionization energy, and HOMO‐LUMO energy gap were calculated by using DFT/B3LYP/6‐311++G(d,p) level. Using the GIAO approach, the 1H and 13C NMR spectra were calculated and showed good agreement with the experimental values. Additionally, the nonlinear optical (NLO) properties of the prepared compounds were found higher than urea. MEP was utilized to ascertain reactive sites within the molecules. The produced compounds exhibited varying degrees of inhibitory effect when tested for their antimicrobial and anticancer properties. The evaluation of ADME (absorption, distribution, metabolism, and excretion) parameters indicated good drug‐like properties of all the investigated compounds.

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Green synthesis, spectroscopic investigation, quantum chemical and molecular docking studies of 3-methylisoxazolo [4,5-b]pyridine

Dhanalakshmi,

Rajesh,

Suresh

et al. 2024

Journal of Molecular Structure

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Quantum computational, Spectroscopic investigations on benzofuranylcarbonylpyrazolopyridine by DFT/TD-DFT: Synthesis, Structure, NBO and NLO research

Cited by 9 publications

References 39 publications

Synthesis, Characterization and Antimicrobial and Anticancer Evaluations of Some Novel Heteroannulated Difuro[3,2-c:3′,2′-g]Chromenes

Synthesis, Characterization and Antimicrobial and Anticancer Evaluations of Some Novel Heteroannulated Difuro[3,2-c:3′,2′-g]Chromenes

Recyclization of 3‐substituted‐6,8‐dimethylchromones with some heterocyclic enamines: Spectroscopic, quantum calculations (HOMO–LUMO, MEP, NLO), biological evaluation, and ADME investigation

Green synthesis, spectroscopic investigation, quantum chemical and molecular docking studies of 3-methylisoxazolo [4,5-b]pyridine

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