Glioblastoma-specific anticancer activity of newly synthetized 3,5-disubstituted isoxazole and 1,4-disubstituted triazole-linked tyrosol conjugates.
Antineoplastic Agents
/ chemical synthesis
Apoptosis
/ drug effects
Cell Proliferation
/ drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Glioblastoma
/ drug therapy
Humans
Isoxazoles
/ chemistry
Molecular Structure
Phenylethyl Alcohol
/ analogs & derivatives
Structure-Activity Relationship
Triazoles
/ chemistry
Tumor Cells, Cultured
Antiproliferative activity
Isoxazoles
Microwave-assisted synthesis
Triazoles
Tyrosol
Journal
Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703
Informations de publication
Date de publication:
09 2021
09 2021
Historique:
received:
16
11
2020
revised:
10
05
2021
accepted:
05
06
2021
pubmed:
16
6
2021
medline:
15
12
2021
entrez:
15
6
2021
Statut:
ppublish
Résumé
Two series of 3,5-disubstituted isoxazoles (6a-e) and 1,4-disubstituted triazoles (8a-e) derivatives have been synthesized from tyrosol (1), a natural phenolic compound, detected in several natural sources such as olive oil, and well-known by its wide spectrum of biological activities. Copper-catalyzed microwave-assisted 1,3-dipolar cycloaddition reactions between tyrosol-alkyne derivative 2 and two series of aryl nitrile oxides (5a-e) and azides (7a-e) regiospecifically afforded 3,5-disubstituted isoxazoles (6a-e) and 1,4-triazole derivatives (8a-e), respectively in quantitative yields. Synthesized compounds were purified and characterized by spectroscopic means including 1D and 2D NMR techniques and HRMS analysis. The newly prepared hybrid molecules have been evaluated for their anticancer and hemolytic activities. Results showed that most derivatives displayed significant antiproliferative activity against human glioblastoma cancer cells (U87) in a dose-dependent manner. Compounds 6d (IC
Identifiants
pubmed: 34130108
pii: S0045-2068(21)00448-X
doi: 10.1016/j.bioorg.2021.105071
pii:
doi:
Substances chimiques
Antineoplastic Agents
0
Isoxazoles
0
Triazoles
0
4-hydroxyphenylethanol
1AK4MU3SNX
Phenylethyl Alcohol
ML9LGA7468
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
105071Informations de copyright
Copyright © 2021 Elsevier Inc. All rights reserved.