Issue 46, 2022

Synthesis, antioxidant and antitumoral activity of new 5′-arylchalcogenyl-3′-N-(E)-feruloyl-3′, 5′-dideoxy-amino-thymidine (AFAT) derivatives

Abstract

The synthesis of a new class of 5′-arylchalcogenyl-3′-N-(E)-feruloyl-3′-amino-3′-deoxythymidine (AFAT) derivatives is disclosed. The compounds were obtained in good yields by an amidation reaction employing soft conditions. Both antitumoral activity against bladder carcinoma cells T24 and the antioxidant effect of the new derivatives were assessed. The results obtained demonstrated a notable inhibition of TBARS production and the DPPH scavenging activity compared with the commercial standards or the precursor building blocks. Additionally, the tellurium AFAT derivatives showed prominent antiproliferative activities. The in vivo studies revealed that the mice group treated with AFAT derivatives kept a normal healthy condition after 1 week of treatment and no kidney or liver toxicity was observed in the in vivo biochemical assays. The in silico evaluation corroborated the experimental results and demonstrated a prominent ability of these compounds to be employed as multitarget drugs.

Graphical abstract: Synthesis, antioxidant and antitumoral activity of new 5′-arylchalcogenyl-3′-N-(E)-feruloyl-3′, 5′-dideoxy-amino-thymidine (AFAT) derivatives

Supplementary files

Article information

Article type
Paper
Submitted
14 jul. 2022
Accepted
17 oct. 2022
First published
19 oct. 2022

New J. Chem., 2022,46, 22306-22313

Synthesis, antioxidant and antitumoral activity of new 5′-arylchalcogenyl-3′-N-(E)-feruloyl-3′, 5′-dideoxy-amino-thymidine (AFAT) derivatives

J. G. Leal, B. C. Piccoli, C. S. Oliveira, F. D’Avila da Silva, F. B. Omage, J. B. T. D. Rocha, M. S. Sonego, N. V. Segatto, F. K. Seixas, T. V. Collares, R. S. da Silva, J. M. Sarturi, L. Dornelles, M. A. F. Faustino and O. E. D. Rodrigues, New J. Chem., 2022, 46, 22306 DOI: 10.1039/D2NJ03487E

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