Synthesis, crystal structure analysis, spectral investigations, DFT computations, Biological activities and molecular docking of methyl(2E)-2-{[N-(2-formylphenyl)(4-methylbenzene) sulfonamido]methyl}-3-(4-fluorophenyl)prop-2-enoate, a potential bioactive agent

Murugavel, S.; velan, V. Vetri; Kannan, D.; Bakthadoss, Manickam

doi:10.1016/j.molstruc.2015.11.047

Cited by 26 publications

(9 citation statements)

References 75 publications

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“…The 13 C NMR spectra of 4CLPBIC that show the signal (experimental) at 139.81 ppm ( δ C‐Cl ) is allotted to C15 atom, which is bonded with a chlorine atom is computed (DFT) as 139.92 ppm and it correlates with Murugavel et al [72]. Similarly, 13 C NMR spectra of 4BRPBIC and 3BRPBIC show the signals (experimental) at 138.41 and 138.48 ppm ( δ CBr ) are allotted to C15 and C14 atoms, which are bonded with a bromine atom is computed (DFT) as 138.26 and 136.22 ppm.…”

Section: Resultssupporting

confidence: 52%

“…Similarly, for 4BRPBIC, it ranges at 175.90–27.85 ppm and 174.66–28.56 ppm, and for 3BRPBIC, the range lies at 175.99–28.85 ppm and 171.83–27.95 ppm. In 13 C‐NMR spectra of 4CLPBIC, 4BRPBIC, and 3BRPBIC, the signals at 176.22 ppm, 175.90 ppm, and 175.99 ppm occur because the C18 atom interacts with sulfur atom S1 ( δ CS) that correlates with Murugavel et al [72]. For the same, the DFT chemical shift is identified at 175.05, 174.66, and 171.83 ppm.…”

Section: Resultsmentioning

confidence: 79%

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Synthesis, spectral, crystal structure, drug‐likeness, in silico, and in vitro biological screening of halogen [Cl, Br] substituted N‐phenylbenzo[g]indazole derivatives as antimicrobial agents

Murugavel

Jayakumar

Chandrasekaran

et al. 2021

Journal of Heterocyclic Chem

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The N‐phenylbenzo[g]indazole derivatives, 3‐(4‐chlorophenyl)‐3,3a,4,5‐tetrahydro‐N‐phenylbenzo[g]indazole‐2‐carbothioamide (4CLPBIC), 3‐(4‐bromophenyl)‐3,3a,4,5‐tetrahydro‐N‐phenylbenzo[g]indazole‐2‐carbothioamide (4BRPBIC), and 3‐(3‐bromophenyl)‐3,3a,4,5‐tetrahydro‐N‐phenylbenzo[g]indazole‐2‐carbothioamide (3BRPBIC), were synthesized by the one‐pot green amalgamation of solvent‐free granulating methodology procedure at room temperature. The synthesized crystals were characterized by single‐crystal X‐ray diffraction (SC‐XRD), FT‐IR, FT‐Raman, NMR, and UV–Vis techniques. The molecular geometries from XRD experimental values of synthesized compounds 4CLPBIC, 4BRPBIC, and 3BRPBIC in the ground state are compared theoretically by applying the density functional theory (DFT), a method with the B3LYP/6‐311G(d,p) basis set using Gaussian 09 software. The vibrational assignments of the synthesized compounds were studied based on potential energy distribution (PED) by the VEDA4 program. The scaled DFT/B3LYP/6‐311G(d,p) results show the best agreement with the experimental values. Computational 1H and 13C NMR were acquired by utilizing gauge‐independent atomic orbital (GIAO) procedure, and chemical shift results are in good agreement with the experimental values. A web‐based theoretical investigation was performed to understand the drug‐likeness and ADMET properties of the compounds. Molecular docking studies were carried out against bacterial cholesterol inhibitor block and inhibitor of lanosterol‐14α‐demethylase CYP51 used in the treatment of topical and systemic mycoses in fungal to understand the inhibitory activity of synthesized compounds. The synthesized molecules were also tested for antibacterial and antifungal activities.

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Section: Resultssupporting

confidence: 52%

Section: Resultsmentioning

confidence: 79%

Synthesis, spectral, crystal structure, drug‐likeness, in silico, and in vitro biological screening of halogen [Cl, Br] substituted N‐phenylbenzo[g]indazole derivatives as antimicrobial agents

Murugavel

Jayakumar

Chandrasekaran

et al. 2021

Journal of Heterocyclic Chem

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“…The stability as well as reactivity of a chemical system was correlated to chemical potential and global hardness values [59] . The stability had a direct relation with global hardness, whereas it had an inverse relationship to its reactivity [60] .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, crystal structure, computational study and anti-virus effect of mixed ligand copper (II) complex with ONS donor Schiff base and 1, 10-phenanthroline

Mohan

Choudhary

2021

Journal of Molecular Structure

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This work deals with the synthesis, crystal structure, computational study and antiviral potential of mixed ligand copper(II) complex [Cu(L)(phen)]( 1 ), (where, H 2 L = ( Z )- N ’-(( E )-2-hydroxy-3,5-diiodobenzylidene)- N,N- dimethylcarbamohydrazonothioic acid, phen = 1,10-phenanthroline). The Schiff base ligand (H 2 L) is coordinated with Cu(II) ion in O, N, S-tridentate mode. The copper complex ( 1 ) crystallized in the monoclinic system of the space group P21/c with eight molecules in the unit cell and reveals a square pyramidal geometry. Furthermore, we also perform quantum chemical calculations to get insights into the structure-property relationship and functional properties of ligand (H 2 L) and its copper (II) complex [Cu(L)(phen)]( 1 ). Complex [Cu(L)(phen)]( 1 ) was also virtually designed in-silico evaluation by Swiss-ADME. Additionally, inspiring by recent developments to find a potential inhibitor for the COVID-19 virus, we have also performed molecular docking study of ligand and its copper complex ( 1 ) to see if our compounds shows an affinity for the main protease (M pro ) of COVID-19 spike protein (PDB ID: 7C8U ). Interestingly, the results are found quite encouraging where the binding affinity and inhibition constant were found to be -7.14 kcal/mol and 5.82 μM for ligand (H 2 L) and -6.18 kcal/mol and 0.76 μM for complex [Cu(L)(phen)]( 1 ) with M pro protein. This binding affinity is reasonably well as compared to recently known antiviral drugs. For instance, the binding affinity of ligand and complex was found to be better than docking results of chloroquine (-6.293 kcal/mol), hydroxychloroquine (-5.573 kcal/mol) and remdesivir (-6.352 kcal/mol) with M pro protein. The present study may offer the technological solutions and potential inhibition to the COVID-19 virus in the ongoing and future challenges of the global community. In the framework of synthesis and characterization of mixed ligand copper (II) complex; the major conclusions can be drawn as follow:

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“…The values of the global reactivity parameters are listed in Table 5 . Overall, the electron donating and accepting abilities were described by ionization potential and electron affinity [64] . The Global reactivity parameters (GRPs) explicated that all the complexes showed greater electron affinity (EA) than the ionization potential (IP) ( Table 5 ); hence, complexes have greater electron-accepting ability.…”

Section: Resultsmentioning

confidence: 99%

“…The Global reactivity parameters (GRPs) explicated that all the complexes showed greater electron affinity (EA) than the ionization potential (IP) ( Table 5 ); hence, complexes have greater electron-accepting ability. The stability as well as reactivity of a chemical system was correlated to chemical potential and global hardness values [64] . The stability had a direct relation with global hardness, whereas it had an inverse relationship to its reactivity [65] .…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis and characterization of novel Ni(II) and Cu(II) complexes as antivirus drug candidates against SARS-CoV-2 and HIV virus

Aprajita

Choudhary

2022

Journal of Molecular Structure

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Synthesis, crystal structure analysis, spectral investigations, DFT computations, Biological activities and molecular docking of methyl(2E)-2-{[N-(2-formylphenyl)(4-methylbenzene) sulfonamido]methyl}-3-(4-fluorophenyl)prop-2-enoate, a potential bioactive agent

Cited by 26 publications

References 75 publications

Synthesis, spectral, crystal structure, drug‐likeness, in silico, and in vitro biological screening of halogen [Cl, Br] substituted N‐phenylbenzo[g]indazole derivatives as antimicrobial agents

Synthesis, spectral, crystal structure, drug‐likeness, in silico, and in vitro biological screening of halogen [Cl, Br] substituted N‐phenylbenzo[g]indazole derivatives as antimicrobial agents

Synthesis, crystal structure, computational study and anti-virus effect of mixed ligand copper (II) complex with ONS donor Schiff base and 1, 10-phenanthroline

Design, synthesis and characterization of novel Ni(II) and Cu(II) complexes as antivirus drug candidates against SARS-CoV-2 and HIV virus

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