Exploration of Indolo[3,2c]isoquinoline derived triazoles as potential antimicrobial and DNA cleavage agents: Synthesis, DFT calculations, and molecular modeling studies

Bioorganic Chemistry, Год журнала: 2023, Номер 137, С. 106598 - 106598

Опубликована: Май 9, 2023

Язык: Английский

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Corrosion Inhibition and Adsorption Properties of N-{2-[2-(5-Methyl-1H-pyrazol-3-yl)acetamido]phenyl}benzamide Monohydrate on C38 Steel in 1 M HCl: Insights from Electrochemical Analysis, DFT, and MD Simulations

ACS Omega, Год журнала: 2025, Номер 10(6), С. 6244 - 6257

Опубликована: Фев. 3, 2025

The heterocyclic compound N-{2-[2-(5-methyl-1H-pyrazol-3-yl)acetamido]-phenyl}benzamide monohydrate (MPAPB) was synthesized and structurally characterized by using nuclear magnetic resonance (NMR), mass spectrometry, infrared (IR) spectroscopy. Its corrosion inhibition performance for C38 in 1 M HCl evaluated gravimetric weight loss measurements, electrochemical impedance spectroscopy (EIS), potentiodynamic polarization (PDP) techniques. MPAPB demonstrated a high efficiency of 90.2% at concentration mM, accompanied substantial decrease the current density. Electrochemical results revealed that acts as mixed-type inhibitor, reducing both anodic cathodic reactions, while increasing charge transfer resistance (R p) decreasing double-layer capacitance (C dl), indicative effective surface adsorption. adsorption behavior consistent with Langmuir isotherm, suggesting combination physical chemical mechanisms. Density functional theory (DFT) calculations molecular dynamics (MD) simulations further elucidated interaction between steel surface, highlighting role electron-donating heteroatoms π-electron systems These theoretical findings were agreement experimental results, confirming formation protective layer inhibits corrosion.

Язык: Английский

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Investigating the molecular interactions of 11-substituted-1-(4-chlorophenyl)-8H-indolo[3,2-c][1,2,4]triazolo[3,4-a]isoquinolines for Antimicrobial Potential: Synthesis, Spectral, In vitro and In silico study interpretations

Journal of Molecular Structure, Год журнала: 2024, Номер 1312, С. 138617 - 138617

Опубликована: Май 12, 2024

Язык: Английский

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In vitro bioactivities and in silico enzyme interactions of abietatrien-3 β -ol by bio-guided isolation from Nepeta italica subsp. italica

Journal of Biomolecular Structure and Dynamics, Год журнала: 2024, Номер unknown, С. 1 - 24

Опубликована: Март 5, 2024

Abietatrien-3β-ol (ATO) was isolated from the aerial part of Nepeta italica subsp. methanol-chloroform extract and studied antioxidant, enzyme inhibition, DNA protection activities. The plant fractionated by silica gel column chromatography using four different solvents. After active chloroform fraction divided into six subfractions under guidance bioactivity, ATO fourth subfraction. molecular structure determined NMR techniques confirmed with literature data. In antioxidant test, showed excellent DPPH˙ (IC50-1.18 ± 0.11 µg/mL), ABTS˙+ (IC50-1.82 0.00 metal chelating (IC50-2.90 0.05 superoxide anion scavenging (IC50-11.59 0.27 reducing power (A0.5-21.09 1.42 H2O2 (A0.5-57.81 4.54 phosphomolybdenum (A0.5-124.23 0.69 µg/mL) activities when compared to standards. potential also found be strong in Form I (47.89%) II (4.56%) formations. had high inhibitions AChE (IC50-1.25 0.04 BChE (IC50-1.26 0.03 lipase (IC50-7.58 tyrosinase (IC50-9.60 µg/mL). docking studies, a binding affinity α-amylase (−8.80 kcal/mol), (−8.10 urease kcal/mol) enzymes. addition, detailing interaction key enzymes that give best interactions through dynamics performing ADMET DFT calculations, it tried explain could suitable drug candidate. light these is thought an effective inhibitor protective molecule against oxidation its properties.

Язык: Английский

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Synthesis, Spectral Analysis, DFT Calculations, in Vitro Screening, and Molecular Docking of New Metal Complexes with Quinoline and Isoniazid Schiff Base as Antimicrobial and Antioxidant Agents

Polycyclic aromatic compounds, Год журнала: 2023, Номер 44(8), С. 5439 - 5459

Опубликована: Окт. 10, 2023

AbstractWe herein report the synthesis, spectral analysis, DFT calculations, in vitro and silico biological activities of novel N'-((2-thioxo-1,2-dihydroquinolin-3 yl)methylene)isonicotinohydr-azide with its Cu(II), Co(II), Ni(II), Zn(II) complexes have been successfully prepared. The ligand were characterized by analytical, FT-IR, 1H NMR, mass, UV–visible spectroscopy, molar conductivity, magnetic susceptibility measurements. Density Functional Theory (DFT) estimations for at DFT/B3LYP level via 6-31 G++ (d, p) replicate structure geometry. Furthermore, molecular docking ADME calculations also performed to correlate interpret experimental results. antimicrobial activity study illustrated enhancement free upon complex formation, Cu(II) (MIC 25 µg mL−1) may be considered a promising antibacterial agent, Ni(II) as antifungal agent. Also, synthesized metal 3.125 showed anti-TB against Mycobacterium tuberculosis. In antioxidant activity, excellent compared standard drugs studies carried out Cytochrome c Peroxidase (PDB ID: 2X08).Keywords: AntimicrobialADME-ToxantioxidantDFTisoniazidtransition complexesquinoline AcknowledgementsThe authors are grateful UGC-CPE, New Delhi K FIST (VGST, Government Karnataka) providing grants form laboratory facilities. thankful Principal, Guru Nanak First Grade College, Bidar We STIC Cochin University SAIF Punjab University, data. author BSM thanks UGC funding (2029-MRP/15-16KABA057/UGC-SWRO). Director, Skanda Life Sciences Pvt. Ltd., Sunkadakatte, Bengaluru studies.Disclosure statementNo potential conflict interest was reported authors.

Язык: Английский

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Investigation of Novel 2‐(Chloromethyl)‐5‐(3, 5‐Disubstituted‐1H‐Indol‐2‐yl)‐1,3,4‐Oxadiazole Derivatives as In Vitro, and In Silico Bioactivity Potential: Anti‐inflammatory, Anti‐TB and Antioxidant Activities Study

ChemistrySelect, Год журнала: 2024, Номер 9(33)

Опубликована: Сен. 4, 2024

Abstract A series of novel 2‐(chloromethyl)‐5‐(3, 5‐disubstituted‐1 H ‐indol‐2‐yl)‐1,3,4‐oxadiazole ( 3 a – h ) derivatives have been synthesized as potential COX inhibitors, anti‐TB, and anti‐oxidant activities. The structures were confirmed by IR, NMR 1 13 C) mass spectral techniques. physicochemical properties, ADME, drug‐likeness profile for the compounds evaluated SwissADME. Based on our interest in indole chemistry SAR study, foresaid examined vitro inhibitory activity, antioxidant ADME studies disclosed newly compounds. , b c recognized outstanding COX‐II inhibitions with IC 50 values 0.28, 0.24, 0.45 μM compared to standard drugs. ,and showed anti‐TB activity MIC value 0.78 μg/mL. attested at 10 μg/ml rate inhibition 66.52 %, 68.25 65.95 % respectively. Finally, molecular docking carried out cyclooxygenase‐2 PDB ID: 6COX ), M. tuberculosis enoyl reductase (INHA) complexed 1‐cyclohexyl‐ N ‐(3,5‐dichlorophenyl)‐5‐oxopyrrolidine‐3‐carboxamide 4TZK cytochrome peroxidase 2X08 all derivatives. selected taken their dynamic studies.

Язык: Английский

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An Investigation into the Synthesis and Characterization of Novel Tetrazole Derivatives for Application as Mild Steel Corrosion Inhibitors in a Solution of Hydrochloric Acid

ACS Omega, Год журнала: 2025, Номер 10(2), С. 2069 - 2080

Опубликована: Янв. 6, 2025

The objective of the study was to synthesize tetrazole molecules featuring nitro groups positioned at para and meta locations. We aimed assess their effectiveness in inhibiting corrosion mild steel a 1 M HCl solution 298 K. Tetrazoles with 2,5-disubstitution were created using [3 + 2] cycloaddition N-alkylation techniques, particular emphasis on synthesizing that contain groups. Tafel polarization experiments, which employ curve approach, used inhibition. Furthermore, quantum chemical calculations density functional theory Monte Carlo simulations investigate connection between molecular structure produced tetrazoles efficacy as inhibitors. results showed 2,5-disubstituted exhibited high inhibition efficiencies, compounds P1 P2 achieving rates 82.7 94.6%, respectively, concentration 10–4 M. confirmed synthesized tetrazoles, while theoretical supported experimental outcomes, establishing strong correlation performance.

Язык: Английский

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Novel D-Ribofuranosyl Tetrazoles: Synthesis, Characterization, In Vitro Antimicrobial Activity, and Computational Studies

ACS Omega, Год журнала: 2025, Номер 10(2), С. 2116 - 2129

Опубликована: Янв. 7, 2025

The goal of this study was to synthesize and evaluate new antimicrobial compounds. We specifically focused on the development 2,5-disubstituted tetrazole derivatives containing O-methyl-2,3-O-isopropylidene-(D)-ribofuranoside groups through N-alkylation reactions. synthesized compounds were characterized using 1H 13C nuclear magnetic resonance (NMR) spectroscopy. Their antibacterial activity tested against Pseudomonas aeruginosa, Escherichia coli, Streptococcus fasciens, Staphylococcus aureus. Density functional theory (DFT) applied examine electronic properties, including highest occupied molecular orbital (HOMO)–least unoccupied (LUMO) gap, hardness, softness, density states (DOS), electrostatic potential. Additionally, crystal structure modeling protein 7AZ5 performed binding affinities hydrophobic interactions hydrogen bonding. Molecular dynamics simulations carried out for 100 ns OPLS_2005 force field re investigate stability 3c 5c into site. Root-mean-square deviation (RMSD), root mean square fluctuation (RMSF), intermolecular analysis showed that these two may gave relative Several N-ribofuranosyl displayed a strong activity. Compounds 1c particularly effective, with minimum inhibitory concentration (MIC) 15.06 μM 13.37 μM, respectively, E. coli S. aureus both surpassing efficacy chloramphenicol (19.34 μM) ampicillin (28.62 μM). These also energies in modeling, indicating DNA polymerase sliding clamp coli. show promise as potent agents notable chemical favorable profiles. findings suggest serve valuable leads drugs.

Язык: Английский

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Synthesis, X-ray Structure, DFT, Hirshfeld Surface, QTAIM/RDG and Molecular Docking Analysis of 3-methyl-4-nitro-1,1-biphenyl (3-MNB)

Journal of Chemical Crystallography, Год журнала: 2025, Номер unknown

Опубликована: Март 21, 2025

Язык: Английский

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An Investigation of Novel Series of 2-Thioxo-1,3-dithiol-carboxamides as Potential Antispasmodic Agents: Design, Synthesis via Coupling Reactions, Density Functional Theory Calculations, and Molecular Docking

Molecules, Год журнала: 2024, Номер 29(16), С. 3855 - 3855

Опубликована: Авг. 14, 2024

This study reports the synthesis of 2-thioxo-1,3-dithiol-carboxamides (TDTCAs) under mild conditions at room temperature using HBTU as a coupling agent, which significantly improved amide bond formation. The synthesized compounds were characterized several analytical techniques, including 1H and 13C NMR spectroscopy, HRMS, confirming their intended structures structural integrity. A DFT computational B3LYP/6-31G(d,p) level was conducted on four to compare electronic properties molecular structures. results showed that these demonstrated antispasmodic effects jejunum contractions. Molecular docking revealed c d displayed highest scores potassium voltage-gated calcium channels adrenergic receptors. In summary, exhibit effects, potentially blocking alpha-adrenergic receptors channels, thus providing scientific basis for potential use in treating gastrointestinal disorders.

Язык: Английский

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