Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Synthesis of Oxymethyl Derivatives of 1,2, 4-Triazole-3-Carboxamides and Their Biological Activities

Ekaterina Mikhina
ORCID logo ,
Daria Stepanycheva
ORCID logo ,
Varvara P. Maksimova
ORCID logo ,
Olga N. Sineva
ORCID logo ,
Natalya N. Markelova
ORCID logo ,
Lyubov Grebenkina
,
Ekaterina A. Lesovaya
ORCID logo ,
Marianna G. Yakubovskaya
ORCID logo ,
Andrey V. Matveev
ORCID logo ,
Ekaterina M. Zhidkova
* ORCID logo
Version 1 : Received: 18 September 2024 / Approved: 18 September 2024 / Online: 19 September 2024 (03:41:03 CEST)

How to cite: Mikhina, E.; Stepanycheva, D.; Maksimova, V. P.; Sineva, O. N.; Markelova, N. N.; Grebenkina, L.; Lesovaya, E. A.; Yakubovskaya, M. G.; Matveev, A. V.; Zhidkova, E. M. Synthesis of Oxymethyl Derivatives of 1,2, 4-Triazole-3-Carboxamides and Their Biological Activities. Preprints 2024, 2024091419. https://doi.org/10.20944/preprints202409.1419.v1 Mikhina, E.; Stepanycheva, D.; Maksimova, V. P.; Sineva, O. N.; Markelova, N. N.; Grebenkina, L.; Lesovaya, E. A.; Yakubovskaya, M. G.; Matveev, A. V.; Zhidkova, E. M. Synthesis of Oxymethyl Derivatives of 1,2, 4-Triazole-3-Carboxamides and Their Biological Activities. Preprints 2024, 2024091419. https://doi.org/10.20944/preprints202409.1419.v1

Abstract

Ribavirin and its analogues exhibit an in vitro antiproliferative effect in cancer cells. In this work we studied the biological activities of a number of oxymethyl derivatives of ribavirin’s aglycon – 1,2,4-triazole-3-carboxamide. Oxymethyl derivatives of 1,2,4-triazole-3-carboxamide with substitu-tions at the fifth or first position of the triazole ring, were synthesized and their antiproliferative and antimicrobial effects were assessed. For both series the presence of an antiproliferative effect was inves-tigated and in the case of 1-oxymethyl derivatives was shown an antimicrobial potential against a Gram-positive bacteria Micrococcus luteus and Gram-negative bacterium Pseudomonas aeruginosa. The obtained results showed that the n-decyloxymethyl derivatives induced leukemia cell death at low mi-cromolar concentrations. We confirmed that n-decyloxymethyl derivatives of ribavirin inhibited cell cy-cle progression and induced accumulation of leukemia cells in subG1-phase. The molecular docking results suggest that oxymethyl derivatives may act by inhibiting translation initiation due to interfering with eIF4E assembly. The outcome results relived that active derivatives (1- or 5-n-decyloxymethyl-1,2,4-triazole-3-carboxamides) can be considered as a lead compound for anti-cancer treatments.

Keywords

1,2,4-triazole-3-carboxamides; ribavirin; acute lymphoblastic leukemia; chronic myeloid leukemia; cancer treatment; antimicrobial effect

Subject

Medicine and Pharmacology, Oncology and Oncogenics

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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