Design, Synthesis and In Vitro Biological Activity of Novel C-7 Methylene Congeners of Furanoallocolchicinoids

A series of novel heterocyclic colchicine derivatives bearing a C-7 methylene fragment were synthesized via Wittig, Horner–Wadsworth–Emmons and Nenajdenko–Shastin olefination approaches. The in vitro biological activities of the most promising compounds were investigated using MTT assays and cell cy...

Descripción completa

Detalles Bibliográficos
Autores principales: Gracheva, Iuliia A., Svirshchevskaya, Elena V., Shchegravina, Ekaterina S., Malysheva, Yulia B., Sitdikova, Alsu R., Fedorov, Alexey Yu.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10143105/
https://www.ncbi.nlm.nih.gov/pubmed/37111520
http://dx.doi.org/10.3390/pharmaceutics15041034
_version_ 1785033772159205376
author Gracheva, Iuliia A.
Svirshchevskaya, Elena V.
Shchegravina, Ekaterina S.
Malysheva, Yulia B.
Sitdikova, Alsu R.
Fedorov, Alexey Yu.
author_facet Gracheva, Iuliia A.
Svirshchevskaya, Elena V.
Shchegravina, Ekaterina S.
Malysheva, Yulia B.
Sitdikova, Alsu R.
Fedorov, Alexey Yu.
author_sort Gracheva, Iuliia A.
collection PubMed
description A series of novel heterocyclic colchicine derivatives bearing a C-7 methylene fragment were synthesized via Wittig, Horner–Wadsworth–Emmons and Nenajdenko–Shastin olefination approaches. The in vitro biological activities of the most promising compounds were investigated using MTT assays and cell cycle analyses. Compounds with an electron withdrawing group on the methylene fragment exhibited substantial antiproliferative activity towards COLO-357, BxPC-3, HaCaT, PANC-1 and A549 cell lines. The spatial orientation of the substituent at the double bond significantly influenced its biological activity.
format Online
Article
Text
id pubmed-10143105
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-101431052023-04-29 Design, Synthesis and In Vitro Biological Activity of Novel C-7 Methylene Congeners of Furanoallocolchicinoids Gracheva, Iuliia A. Svirshchevskaya, Elena V. Shchegravina, Ekaterina S. Malysheva, Yulia B. Sitdikova, Alsu R. Fedorov, Alexey Yu. Pharmaceutics Article A series of novel heterocyclic colchicine derivatives bearing a C-7 methylene fragment were synthesized via Wittig, Horner–Wadsworth–Emmons and Nenajdenko–Shastin olefination approaches. The in vitro biological activities of the most promising compounds were investigated using MTT assays and cell cycle analyses. Compounds with an electron withdrawing group on the methylene fragment exhibited substantial antiproliferative activity towards COLO-357, BxPC-3, HaCaT, PANC-1 and A549 cell lines. The spatial orientation of the substituent at the double bond significantly influenced its biological activity. MDPI 2023-03-23 /pmc/articles/PMC10143105/ /pubmed/37111520 http://dx.doi.org/10.3390/pharmaceutics15041034 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Gracheva, Iuliia A.
Svirshchevskaya, Elena V.
Shchegravina, Ekaterina S.
Malysheva, Yulia B.
Sitdikova, Alsu R.
Fedorov, Alexey Yu.
Design, Synthesis and In Vitro Biological Activity of Novel C-7 Methylene Congeners of Furanoallocolchicinoids
title Design, Synthesis and In Vitro Biological Activity of Novel C-7 Methylene Congeners of Furanoallocolchicinoids
title_full Design, Synthesis and In Vitro Biological Activity of Novel C-7 Methylene Congeners of Furanoallocolchicinoids
title_fullStr Design, Synthesis and In Vitro Biological Activity of Novel C-7 Methylene Congeners of Furanoallocolchicinoids
title_full_unstemmed Design, Synthesis and In Vitro Biological Activity of Novel C-7 Methylene Congeners of Furanoallocolchicinoids
title_short Design, Synthesis and In Vitro Biological Activity of Novel C-7 Methylene Congeners of Furanoallocolchicinoids
title_sort design, synthesis and in vitro biological activity of novel c-7 methylene congeners of furanoallocolchicinoids
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10143105/
https://www.ncbi.nlm.nih.gov/pubmed/37111520
http://dx.doi.org/10.3390/pharmaceutics15041034
work_keys_str_mv AT grachevaiuliiaa designsynthesisandinvitrobiologicalactivityofnovelc7methylenecongenersoffuranoallocolchicinoids
AT svirshchevskayaelenav designsynthesisandinvitrobiologicalactivityofnovelc7methylenecongenersoffuranoallocolchicinoids
AT shchegravinaekaterinas designsynthesisandinvitrobiologicalactivityofnovelc7methylenecongenersoffuranoallocolchicinoids
AT malyshevayuliab designsynthesisandinvitrobiologicalactivityofnovelc7methylenecongenersoffuranoallocolchicinoids
AT sitdikovaalsur designsynthesisandinvitrobiologicalactivityofnovelc7methylenecongenersoffuranoallocolchicinoids
AT fedorovalexeyyu designsynthesisandinvitrobiologicalactivityofnovelc7methylenecongenersoffuranoallocolchicinoids

Ejemplares similares