Synthesis, characterization and Cytotoxicity Evaluation of New Heterocyclic Compounds with Oxazole Ring Containing  4-(Phenylsulfonyl)phenyl Moiety

Apostol, Theodora Venera; Bărbuceanu, Ștefania Felicia; Socea, Laura Ileana; Drăghici, Constantin; Şaramet, Gabriel; Iscrulescu, Lucian; Olaru, Octavian Tudorel

doi:10.37358/rc.70.19.11.7649

Cited by 5 publications

(9 citation statements)

References 18 publications

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“…Given the therapeutic potential of these scaffolds, that the majority have also shown antimicrobial properties and in the continuation of our research [ 66 , 67 , 68 , 69 , 70 , 71 ], the purpose of this present work was to obtain and characterize new synthetic analogs from N -acyl-α-amino acids, 1,3-oxazol-5(4 H )-ones, N -acyl-α-amino ketones, and 1,3-oxazoles classes derived from valine with a 4-[(4-chlorophenyl)sulfonyl]phenyl moiety and to evaluate their antimicrobial effect and toxic potential.…”

Section: Introductionmentioning

confidence: 88%

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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Section: Introductionmentioning

confidence: 88%

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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“…They can be produced via ribosomal, non-ribosomal approaches or by synthetic pathways [ [193] , [194] , [195] ]. Oxazole-containing peptides derived from marine organisms possess antibacterial [ 196 ], antiviral [ 197 ], anti-malarial [ 198 ] and anti-algal properties [ 199 ].…”

Section: Biomaterials From Marine Organismsmentioning

confidence: 99%

Biomaterials from the sea: Future building blocks for biomedical applications

Wan

Qin

Chen

et al. 2021

Bioactive Materials

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Marine resources have tremendous potential for developing high-value biomaterials. The last decade has seen an increasing number of biomaterials that originate from marine organisms. This field is rapidly evolving. Marine biomaterials experience several periods of discovery and development ranging from coralline bone graft to polysaccharide-based biomaterials. The latter are represented by chitin and chitosan, marine-derived collagen, and composites of different organisms of marine origin. The diversity of marine natural products, their properties and applications are discussed thoroughly in the present review. These materials are easily available and possess excellent biocompatibility, biodegradability and potent bioactive characteristics. Important applications of marine biomaterials include medical applications, antimicrobial agents, drug delivery agents, anticoagulants, rehabilitation of diseases such as cardiovascular diseases, bone diseases and diabetes, as well as comestible, cosmetic and industrial applications.

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“…The aim of the present work was to continue our previous research on 1,3-oxazole derivatives [ 40 , 41 , 42 , 43 , 44 , 45 ], by focusing on the biological evaluation of newly synthesized N -acyl-α-amino acid, 1,3-oxazol-5(4 H )-one, N -acyl-α-amino ketone, and 1,3-oxazole analogs derived from valine containing the 4-(phenylsulfonyl)phenyl substituent.…”

Section: Introductionmentioning

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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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 Evaluation of New Heterocyclic Compounds with Oxazole Ring Containing 4-(Phenylsulfonyl)phenyl Moiety

Cited by 5 publications

References 18 publications

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

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

Biomaterials from the sea: Future building blocks for biomedical applications

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

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