Synthesis and Anticancer Evaluation of New 1,3,4-Oxadiazole Derivatives

Stecoza, Camelia Elena; Nițulescu, George Mihai; Drăghici, Constantin; Cãproiu, Miron Teodor; Olaru, Octavian Tudorel; Bostan, Marinela; Mihăilă, Mirela

doi:10.3390/ph14050438

Cited by 38 publications

(21 citation statements)

References 52 publications

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“…With 24 h prior to the determination, young daphnids were selected according to their size and maintained for 24 h in an artificial medium. Ten daphnids/replicate were used, and the determination was performed in tissue culture plates with 12 wells (Greiner Bio-One) [ 58 , 59 ]. Each compound was tested in six concentrations, ranging from 2.2 to 44 µg/mL.…”

Section: Methodsmentioning

confidence: 99%

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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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Section: Methodsmentioning

confidence: 99%

“…A similarity search was performed on the ChEMBL database for the newly synthesized compounds using a 50% threshold [ 58 ]. The resulting structures were extracted together with their assayed activities on bacteria [ 61 ].…”

Section: Methodsmentioning

confidence: 99%

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

et al. 2021

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“…A 1% DMSO solution as a negative control. For each sample, 10 daphnids were used per replicate and the determination was carried out in duplicate [ 81 , 82 , 83 ]. The lethality was evaluated after 24 and 48 h of exposure.…”

Section: Methodsmentioning

confidence: 99%

“…A similarity search was performed on the ChEMBL database for the compounds 3 , 4 , 5a , b , and 6a , b using a 50% threshold [ 81 ]. The resulting structures were extracted together with their assayed activities on bacteria [ 85 ].…”

Section: Methodsmentioning

confidence: 99%

Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives

et al. 2021

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The multi-step synthesis, physico-chemical characterization, and biological activity of novel valine-derived compounds, i.e., N-acyl-α-amino acids, 1,3-oxazol-5(4H)-ones, N-acyl-α-amino ketones, and 1,3-oxazoles derivatives, bearing a 4-[(4-chlorophenyl)sulfonyl]phenyl moiety are reported here. The structures of the newly synthesized compounds were confirmed by spectral (UV-Vis, FT-IR, MS, 1H- and 13C-NMR) data and elemental analysis results, and their purity was determined by RP-HPLC. The new compounds were assessed for their antimicrobial activity and toxicity to aquatic crustacean Daphnia magna. Also, in silico studies regarding their potential mechanism of action and toxicity were performed. The antimicrobial evaluation revealed that the 2-{4-[(4-chlorophenyl)sulfonyl]benzamido}-3-methylbutanoic acid and the corresponding 1,3-oxazol-5(4H)-one exhibited antimicrobial activity against Gram-positive bacterial strains and the new 1,3-oxazole containing a phenyl group at 5-position against the C. albicans strain.

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“…Each compound was tested in six concentrations ranging from 50 to 1000 µM, and two replicates/concentration. For each replicate, ten daphnids were used, and the testing was performed in 12 well tissue culture plates (Greiner Bio-One, Kremsmünster, Austria) at a final volume/well of 4 mL [58][59][60][61]. Nifedipine in concentrations 1-1000 µM was used as the positive control, and a 1% DMSO solution as a negative control.…”

Section: Daphnia Magna Toxicity Assaymentioning

confidence: 99%

Synthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide

et al. 2021

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A series of new pyrrole derivatives were designed as chemical analogs of the 1,4-dihydropyridines drugs in order to develop future new calcium channel blockers. The new tri- and tetra-substituted N-arylpyrroles were synthesized by the one-pot reaction of 1-methyl-3-cyanomethyl benzimidazolium bromide with substituted alkynes having at least one electron-withdrawing substituent, in 1,2-epoxybutane, acting both as the solvent and reagent to generate the corresponding benzimidazolium N3-ylide. The structural characterization of the new substituted pyrroles was based on IR, NMR spectroscopy as well as on single crystal X-ray analysis. The toxicity of the new compounds was assessed on the plant cell using Triticum aestivum L. species and on the animal cell using Artemia franciscana Kellogg and Daphnia magna Straus crustaceans. The compounds showed minimal phytotoxicity on Triticum rootlets and virtually no acute toxicity on Artemia nauplii, while on Daphnia magna, it induced moderate to high toxicity, similar to nifedipine. Our research indicates that the newly synthetized pyrrole derivatives are promising molecules with biological activity and low acute toxicity.

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Synthesis and Anticancer Evaluation of New 1,3,4-Oxadiazole Derivatives

Cited by 38 publications

References 52 publications

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

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

Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives

Synthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide

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