Synthesis, crystal structure analysis, spectral (NMR, FT-IR, FT-Raman and UV–Vis) investigations, molecular docking studies, antimicrobial studies and quantum chemical calculations of a novel 4-chloro-8-methoxyquinoline-2(1H)-one: An effective antimicrobial agent and an inhibition of DNA gyrase and lanosterol-14α-demethylase enzymes

Murugavel, S.; Sundramoorthy, S.; Lakshmanan, Dinesh Kumar; Subashini, R.; Kumar, Pradeep

doi:10.1016/j.molstruc.2016.11.035

Cited by 24 publications

(10 citation statements)

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“…The sp 4.79 natural atomic hybrid orbital of B7 and sp 1.35 natural atomic hybrid orbital of O25 interact with each other and then form a σ(B7–O25) bond where O25 and B7 make 83.65% and 16.35% contributions, respectively. 85 The properties of the new NBO are of a p -character rich NBO because the interacting atomic hybrid orbitals are controlled by p -character (as shown in Table 6 ). A similar pattern can also be perceived for the CS2 and CS3 conjugated structures.…”

Section: Resultsmentioning

confidence: 99%

A theoretical study of allopurinol drug sensing by carbon and boron nitride nanostructures: DFT, QTAIM, RDG, NBO and PCM insights

et al. 2021

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Section: Resultsmentioning

confidence: 99%

A theoretical study of allopurinol drug sensing by carbon and boron nitride nanostructures: DFT, QTAIM, RDG, NBO and PCM insights

et al. 2021

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“…The binding energy, bond length, and bonding type of interaction in complex ADTNT-DNA gyrase were listed in Table 7. The docking output predicts that the binding affinity of ADTNT-DNA gyrase complex (-7.10 kcal/mol) has comparatively a better binding energy score when compared with Ciprofloxacin-DNA gyrase complex (-4.01 kcal/mol) [42]. The ADTNT-Lanosterol 14αdemethylase complex is stabilized by six hydrogen interactions with residues GLN72, ARG96, and GLY388 as shown in Figure 12b and the binding energy, bond length, and bonding type of interaction in this complex is given in Table 7.…”

Section: Molecular Docking Analysismentioning

confidence: 99%

“…The docking output predicts that the binding affinity of ADTNT-Lanosterol 14α-demethylase complex (-8.80 kcal/mol) is almost twice the binding energy score as in the case of Fluconazole-Lanosterol 14α-demethylase complex (-3.59 kcal/mol) [42]. The ADTNT reveals a strong binding interaction with the targets (DNA gyrase/Lanosterol 14α-demethylase) and have more docking affinity score than the standard drugs (Ciprofloxacin and fluconazole).…”

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confidence: 99%

Synthesis, X-ray crystal structure, DFT, Hirshfeld surfaces, energy frameworks, and molecular docking analysis of a bicyclic ortho-aminocarbonitrile derivative

et al. 2022

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2-Amino-4-(2, 5-dimethoxyphenyl)-4a,5,6,7-tetrahydronaphthalene-1,3,3(4H)-tricarbonitrile has been synthesized and characterized by conventional spectroscopic techniques (FT-IR and 1H NMR) and the three-dimensional structure elucidated by single crystal X-ray diffraction studies (SC-XRD). It exists in monoclinic crystal system with space group P21/c and lattice parameters: a = 14.641(13) Å, b = 8.653(4) Å, c = 16.609(10) Å, β = 116.34(3)°, and Z = 4. In the crystal packing, molecules are connected through N-H···O and N-H···N intermolecular and intramolecular C-H···O interactions. The N1-H11···N2 interaction results in the formation of a dimer corresponding to R22(12) graph-set motif. The molecular structure has been theoretically optimized by using density functional theory (DFT) with the basis set B3LYP/6-311G (d,p). The optimized bond geometry shows consistency with the SC-XRD data. Besides this, the molecular electrostatic potential (MEP), Mulliken charges, and frontier molecular orbital analysis have been described. The dnorm, shape index, curvedness, crystal voids, 2D fingerprint (FP) plots, and 3D energy frameworks using Hirshfeld surface (HS) studies have also been computed and investigated. The molecular docking studies for 2-amino-4-(2, 5-dimethoxyphenyl)-4a,5,6,7-tetrahydronaphthalene-1,3,3(4H)-tricarbonitrile with DNA gyrase/lanosterol 14α-demethylase suggest that the compound may act as an active antimicrobial drug.

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“…DNA gyrase is considered a fundamental type II DNA topoisomerase that maneuvers DNA topology by making temporary double-strand breaks and DNA strand passage. 36 It is considered as an important drug target due to its vital role in bacterial survival. 37 An example of DNA gyrase poisons of commercial importance is ciprofloxacin (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

<p>Novel <em>N</em>-(Substituted) Thioacetamide Quinazolinone Benzenesulfonamides as Antimicrobial Agents</p>

Ghorab

Alqahtani

Soliman

et al. 2020

IJN

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Aim: With the rapid emergence of antibiotic resistance, efforts are being made to obtain new selective antimicrobial agents. Hybridization between quinazolinone and benzenesulfonamide can provide new antimicrobial candidates. Also, the use of nanoparticles can help boost drug efficacy and lower side effects. Materials and Methods: Novel quinazolinone-benzenesulfonamide derivatives 5-18 were synthesized and screened for their antimicrobial activity against Gram-positive bacteria, Gramnegative bacteria, MRSA and yeast. The most potent compound 16 was conjugated with copper oxide nanoparticles 16-CuONPs by gamma irradiation (4.5 KGy). Characterization was performed using UV-Visible, TEM examination, XRD patterns and DLS. Moreover, compound 16 was used to synthesize two nanoformulations: 16-CNPs by loading 16 in chitosan nanoparticles and the nanocomposites 16-CuONPs-CNPs. Characterization of these nanoformulations was performed using TEM and zeta potential. Besides, the inhibitory profile against Staphylococcus aureus DNA gyrase was assayed. Cytotoxic evaluation of 16, 16-CNPs and 16-CuONPs-CNPs on normal VERO cell line was carried out to determine its relative safety. Molecular docking of 16 was performed inside the active site of S. aureus DNA gyrase. Results: Compound 16 was the most active in this series against all the tested strains and showed inhibition zones and MICs in the ranges of 25-36 mm and 0.31-5.0 µg/mL, respectively. The antimicrobial screening of the synthesized nanoformulations revealed that 16-CuONPs-CNPs displayed the most potent activity. The MBCs of 16 and the nanoformulations were measured and proved their bactericidal mode of action. The inhibitory profile against S. aureus DNA gyrase showed IC 50 ranging from 10.57 to 27.32 µM. Cytotoxic evaluation of 16, 16-CNPs and 16-CuONPs-CNPs against normal VERO cell lines proved its relative safety (IC 50 = 927, 543 and 637 µg/mL, respectively). Molecular docking of 16 inside the active site of S. aureus DNA gyrase showed that it binds in the same manner as that of the co-crystallized ligand, ciprofloxacin. Conclusion: Compound 16 could be considered as a new antimicrobial lead candidate with enhanced activity upon nanoformulation.

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Cited by 24 publications

References 84 publications

A theoretical study of allopurinol drug sensing by carbon and boron nitride nanostructures: DFT, QTAIM, RDG, NBO and PCM insights

A theoretical study of allopurinol drug sensing by carbon and boron nitride nanostructures: DFT, QTAIM, RDG, NBO and PCM insights

Synthesis, X-ray crystal structure, DFT, Hirshfeld surfaces, energy frameworks, and molecular docking analysis of a bicyclic ortho-aminocarbonitrile derivative

<p>Novel <em>N</em>-(Substituted) Thioacetamide Quinazolinone Benzenesulfonamides as Antimicrobial Agents</p>

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