Synthesis, Characterization, and Cytotoxicity Assessment of New 4-Benzyl-1,3-Oxazole Derivatives Incorporating 4-[(4-Bromophenyl)sulfonyl]phenyl Fragment

Apostol, Theodora-Venera

doi:10.31925/farmacia.2021.3.15

Cited by 5 publications

(1 citation statement)

References 27 publications

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“…Thus, the mass spectrum of imidazole shows a high abundance of the aziridinium cation at m/z 40. In the literature, deuterium labelling experiments have shown that the loss of hydrogen atoms is specific to positions 4 and 5, while the loss of HCN is less specific, starting in the order of 2 > 4(5) > 1 [32][33][34][35][36][37].…”

Section: Physicochemical Characterization Of the Intermediated Productsmentioning

confidence: 99%

Synthesis, Spectral Characterization and Molecular Docking Studies of New N3-Aryl- And N3-Alkyl-Barbituric Acid Derivatives With Potential Local Anaesthetic Action

NICOLESCU

2023

FARMACIA

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Azoles and their derivatives have generated increasing pharmacological interest due to their properties as well as the wide range of links between structure and biological activity. Herein, starting from Löfgren's principle regarding the synthesis of a local anaesthetic, docking studies took into account the complex architecture of voltage-gated sodium channels, the nature of the membranes, and the way of administering the local anaesthetic. Thus, the present research aims at the spectral characterization and molecular docking studies of the newly synthesized compounds containing an ester-type anaesthetic chain substituted with an azole ring, having a hydrophilic character and a pyrimidine ring, as a lipophilic group. The HPLC, FT-IR, RMN ( 1 H-și 13 C-RMN) and mass spectrometry methods were used to characterize the obtained compounds. Molecular docking studies were performed using the crystal structure of the NavAb voltage-gated sodium channel obtained from the PDB RCSB (PDB ID: 6MVX) database to predict local anaesthetic activity. RezumatAzolii și derivații lor au generat un interes farmacologic în creștere datorită proprietăților lor, precum și a gamei largi de relații dintre structură și activitatea biologică. Pornind de la principiul lui Löfgren în ceea ce privește sinteza unui anestezic local, studiile de docking au luat în considerare arhitectura complexă a canalelor de sodiu voltaj-dependente, natura membranelor și modul de administrare al anestezicului local. Astfel, cercetarea de față are ca scop caracterizarea spectrală și studii de docking molecular a compușilor nou sintetizați care conțin un lanț anesteziofor de tip ester substituit cu un inel azolic, având un caracter hidrofil și un inel pirimidinic, ca grupare lipofilă. Au fost utilizate metodele HPLC, FT-IR, RMN ( 1 H-și 13 C-RMN) și spectrometria de masă pentru a caracteriza compușii obținuți. Studiile de docking molecular au fost efectuate folosind structura cristalină a canalului de sodiu voltaj-dependent NavAb, obținut din baza de date PDB RCSB (PDB ID: 6MVX) pentru a prezice activitatea anestezică locală.

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Section: Physicochemical Characterization Of the Intermediated Productsmentioning

confidence: 99%

Synthesis, Spectral Characterization and Molecular Docking Studies of New N3-Aryl- And N3-Alkyl-Barbituric Acid Derivatives With Potential Local Anaesthetic Action

NICOLESCU

2023

FARMACIA

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In Silico and In Vitro Assessment of Antimicrobial and Antibiofilm Activity of Some 1,3-Oxazole-Based Compounds and Their Isosteric Analogues

et al. 2022

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In this paper, we report on the antimicrobial activity assessment of 49 compounds previously synthesized as derivatives of alanine or phenylalanine that incorporate a 4-(4-X-phenylsulfonyl)phenyl fragment (X = H, Cl, or Br), namely 21 acyclic compounds (6 × N-acyl-α-amino acids, 1 × N-acyl-α-amino acid ester, and 14 × N-acyl-α-amino ketones) and 28 pentatomic heterocycles from the oxazole-based compound class (6 × 4H-1,3-oxazol-5-ones, 16 × 5-aryl-1,3-oxazoles, and 6 × ethyl 1,3-oxazol-5-yl carbonates). Both in silico and in vitro qualitative and quantitative assays were used to investigate the antimicrobial potential of these derivatives against planktonic and biofilm-embedded microbial strains. Some of the tested compounds showed promising antimicrobial and antibiofilm activity depending on their chemical scaffold and lipophilic character.

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Synthesis and Biological Evaluation of New N-Acyl-α-amino Ketones and 1,3-Oxazoles Derivatives

et al. 2021

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In order to develop novel bioactive substances with potent activities, some new valine-derived compounds incorporating a 4-(phenylsulfonyl)phenyl fragment, namely, acyclic precursors from N-acyl-α-amino acids and N-acyl-α-amino ketones classes, and heterocycles from the large family of 1,3-oxazole-based compounds, were synthesized. The structures of the new compounds were established using elemental analysis and spectral (UV-Vis, FT-IR, MS, NMR) data, and their purity was checked by reversed-phase HPLC. The newly synthesized compounds were evaluated for their antimicrobial and antibiofilm activities, for toxicity on D. magna, and by in silico studies regarding their potential mechanism of action and toxicity. The 2-aza-3-isopropyl-1-[4-(phenylsulfonyl)phenyl]-1,4-butanedione 4b bearing a p-tolyl group in 4-position exhibited the best antibacterial activity against the planktonic growth of both Gram-positive and Gram-negative strains, while the N-acyl-α-amino acid 2 and 1,3-oxazol-5(4H)-one 3 inhibited the Enterococcus faecium biofilms. Despite not all newly synthesized compounds showing significant biological activity, the general scaffold allows several future optimizations for obtaining better novel antimicrobial agents by the introduction of various substituents on the phenyl moiety at position 5 of the 1,3-oxazole nucleus.

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Synthesis, Characterization, and Cytotoxicity Assessment of New 4-Benzyl-1,3-Oxazole Derivatives Incorporating 4-[(4-Bromophenyl)sulfonyl]phenyl Fragment

Cited by 5 publications

References 27 publications

Synthesis, Spectral Characterization and Molecular Docking Studies of New N3-Aryl- And N3-Alkyl-Barbituric Acid Derivatives With Potential Local Anaesthetic Action

Synthesis, Spectral Characterization and Molecular Docking Studies of New N3-Aryl- And N3-Alkyl-Barbituric Acid Derivatives With Potential Local Anaesthetic Action

In Silico and In Vitro Assessment of Antimicrobial and Antibiofilm Activity of Some 1,3-Oxazole-Based Compounds and Their Isosteric Analogues

Synthesis and Biological Evaluation of New N-Acyl-α-amino Ketones and 1,3-Oxazoles Derivatives

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