Synthesis of 5-(5-methyl-benzofuran-3-ylmethyl)-3H- [1, 3, 4] oxadiazole-2-thione and investigation of its spectroscopic, reactivity, optoelectronic and drug likeness properties by combined computational and experimental approach

Hiremath, Sudhir M.; Suvitha, A.; Patil, N. R.; Hiremath, Chidanandayya S.; Khemalapure, Seema S.; Pattanayak, Subrat Kumar; Negalurmath, Veerabhadrayya S.; Kotresh, Obelannavar; Armaković, Sanja J.

doi:10.1016/j.saa.2018.07.003

Cited by 49 publications

(12 citation statements)

References 77 publications

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“…Generally computed vibrational wavenumbers are found to be greater than the experimentally obtained wavenumbers. Hence to obtain proper comparison between experimental and theoretical wave numbers, the theoretical wavenumbers are scaled by the scaling factor of 0.9614 [17]. The entire vibrational assignments for the computed wave numbers of the title molecule is conducted with the help of PED (%) acquired by VEDA 04 software [18].…”

Section: Methodsmentioning

confidence: 99%

Synthesis, spectroscopic (FT-IR, FT-Raman, NMR & UV-Vis), reactive (ELF, LOL, Fukui), drug likeness and molecular docking insights on novel 4-[3-(3-methoxy-phenyl)-3-oxo-propenyl]-benzonitrile by experimental and computational methods

Radder

Melavanki

Hiremath

et al. 2021

Heliyon

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The spectroscopic analysis such as FT-IR, FT-Raman, UV-Vis and NMR are conducted for the synthesized molecule by both experimental and theoretical approach. The theoretical computations were achieved by DFT method with B3LYP functional and 6–311 ++ G (d, P) basis set. Firstly the geometrical parameters obtained by DFT are compared with the related experimental parameters. Experimental FT-IR and FT-Raman spectra of the title molecule have been acquired. The vibrational analysis is conducted and the assignments concerned to the observed bands are mentioned through the potential energy distribution (PED). The GIAO method was employed for theoretical NMR analysis and the results are compared with experimental chemical shifts. In accumulation to these analyses NLO, NBO, FMO and MEP analysis have been conducted to understand the nature of the molecule. ELF and LOL were performed. The drug likeness and molecular docking studies also conducted. The potency of inhibition of molecule against M PRO and PL PRO receptors has been performed using molecular docking studies.

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Section: Methodsmentioning

confidence: 99%

Synthesis, spectroscopic (FT-IR, FT-Raman, NMR & UV-Vis), reactive (ELF, LOL, Fukui), drug likeness and molecular docking insights on novel 4-[3-(3-methoxy-phenyl)-3-oxo-propenyl]-benzonitrile by experimental and computational methods

Radder

Melavanki

Hiremath

et al. 2021

Heliyon

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“…Benzofurans: 2017 Differentiation of 6-MAPB and its positional isomer, 2-MAPB by GC-MS and GC-MS/MS [ 908 ]; 2018 experimental and theoretical FT-IR, FT-Raman, H-1 NMR, C-13 NMR and UV–Vis spectral studies on 2-DBAA [ 909 ]; 5MBOT characterization by FT-IR, FT-Raman, H-1 NMR, C-13 NMR and UV spectral studies [ 910 ]; synthesis and characterization of HBFAA by FT-IR, FT-Raman and NMR [ 911 ]; 2019 synthesis of a range of polycyclic benzofurans [ 912 ]; synthesis of 2,3-disubstituted benzofurans [ 913 ]; synthesis of substituted 2-methylbenzofuran [ 914 ]; one-pot synthesis of benzofurans and naphtho [2,3-b]furans [ 915 ].…”

Section: Routine and Improved Analyses Of Abused Substancesmentioning

confidence: 99%

Interpol review of controlled substances 2016–2019

Jones

Comparin

2020

Forensic Science International: Synergy

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“…Recently, there are ongoing efforts to utilize benzofuran hydrazones as potential scaffolds in the development of multifunctional drugs [ 12 ]. The use of molecular docking studies also suggested antimicrobial and antifungal activity of the probe molecules [ 13 , 14 ]. Studies have also been carried out on the benzofuran derivative 2MBA in terms of its spectroscopic, quantum chemical, molecular docking, and drug likeness parameter properties.…”

Section: Introductionmentioning

confidence: 99%

Modulation of benzofuran structure as a fluorescent probe to optimize linear and nonlinear optical properties and biological activities

Krawczyk

2020

J Mol Model

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The study presents the influence of structure modulation by introducing selected donor and acceptor substituents on optical properties of benzofuran used in biological imaging. As the starting form, 2-(5-formylbenzofuran-2-yl)acetamide described experimentally was used. This molecule contains an aldehyde group as reactive site, through which conjugation with protein occurs. Structure modulation was carried out by attaching additional electron-donating and electron-withdrawing substituents to the amino group, namely -NH2, -NHCH3, -NO2, -OH, and -OCH3. Studies have shown that the -NH2, -NHCH3, -OH, and -OCH3 substituents do not induce a significant change in the position of maximum absorption and fluorescence relative to each other. They also do not change the parameters describing the nonlinear response. Only the presence of the -NO2 substituent results in significant solvatochromic shifts. Changing substituents also does not significantly affect the LD50 value, and all tested fluorescent probes should not be considered toxic to humans. Modulation of the benzofuran derivative structure also does not change the active center in which the biocomplex with the protein is formed. In each case, the conjugation takes place via LYS114. In addition, the study was prompted to analyze the linear and nonlinear optical properties of conjugates formed after the reaction with Concanavalin A. Graphical abstract

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Synthesis of 5-(5-methyl-benzofuran-3-ylmethyl)-3H- [1, 3, 4] oxadiazole-2-thione and investigation of its spectroscopic, reactivity, optoelectronic and drug likeness properties by combined computational and experimental approach

Cited by 49 publications

References 77 publications

Synthesis, spectroscopic (FT-IR, FT-Raman, NMR & UV-Vis), reactive (ELF, LOL, Fukui), drug likeness and molecular docking insights on novel 4-[3-(3-methoxy-phenyl)-3-oxo-propenyl]-benzonitrile by experimental and computational methods

Synthesis, spectroscopic (FT-IR, FT-Raman, NMR & UV-Vis), reactive (ELF, LOL, Fukui), drug likeness and molecular docking insights on novel 4-[3-(3-methoxy-phenyl)-3-oxo-propenyl]-benzonitrile by experimental and computational methods

Interpol review of controlled substances 2016–2019

Modulation of benzofuran structure as a fluorescent probe to optimize linear and nonlinear optical properties and biological activities

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