Dataset Information

Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles.

ABSTRACT: The reaction of 5-aryl-NH-tetrazoles with adamantan-1-ol in concentrated sulfuric acid proceeds regioselectively with the formation of the corresponding 2-adamantyl-5-aryl-2H-tetrazoles. Nitration of these compounds leads to 2-(adamantan-1-yl)-5-(3-nitroaryl)-2Htetrazoles. The structures and composition of the obtained novel 2-adamantyl-5-aryltetrazoles were proven by IR spectroscopy, ¹H and ¹³C NMR spectroscopy, high-resolution mass spectrometry, and also by X-ray structural analysis. According to the simultaneous thermal analysis data, the obtained compounds are thermally stable up to a temperature of about 150°C. In vitro studies have shown that some of the 2-adamantyl-5-aryltetrazoles exhibit moderate inhibitory activity against influenza A (H1N1) virus. The antiviral selectivity index (SI) of 2-[2-(adamantan-1-yl)-2H-tetrazol-5-yl]-6-bromo-4-nitroaniline is significantly higher (SI 11) than that of the reference drug rimantadine (SI 5).

Supplementary information

The online version contains supplementary material available at 10.1007/s10593-021-02931-5.

SUBMITTER: Mikolaichuk OV

PROVIDER: S-EPMC8149581 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles.

Mikolaichuk Olga V OV Zarubaev Vladimir V VV Zarubaev Vladimir V VV Muryleva Anna А AА Esaulkova Yana L YL Spasibenko Daria V DV Batyrenko Alina А AА Kornyakov Ilya V IV Trifonov Rostislav Е RЕ

Chemistry of heterocyclic compounds 20210526 4

The reaction of 5-aryl-NH-tetrazoles with adamantan-1-ol in concentrated sulfuric acid proceeds regioselectively with the formation of the corresponding 2-adamantyl-5-aryl-2H-tetrazoles. Nitration of these compounds leads to 2-(adamantan-1-yl)-5-(3-nitroaryl)-2Htetrazoles. The structures and composition of the obtained novel 2-adamantyl-5-aryltetrazoles were proven by IR spectroscopy, 1H and 13C NMR spectroscopy, high-resolution mass spectrometry, and a ...[more]

PMID: 34054132

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

Dataset Information

Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles.

Supplementary information

Publications

Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2<i>H</i>-tetrazoles.

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