Synthesis of metronidazole based thiazolidinone analogs as promising antiamoebic agents.
Amebicides
/ chemical synthesis
Catalytic Domain
Entamoeba histolytica
/ drug effects
HEK293 Cells
Humans
Metronidazole
/ chemical synthesis
Molecular Docking Simulation
Molecular Structure
Parasitic Sensitivity Tests
Protein Binding
Protozoan Proteins
/ chemistry
Quantitative Structure-Activity Relationship
Sulfatases
/ chemistry
Thiazolidines
/ chemical synthesis
Amoebiasis
Entamoeba histolytica
Metronidazole
Molecular docking
Thiazolidinone
Journal
Bioorganic & medicinal chemistry letters
ISSN: 1464-3405
Titre abrégé: Bioorg Med Chem Lett
Pays: England
ID NLM: 9107377
Informations de publication
Date de publication:
01 12 2020
01 12 2020
Historique:
received:
16
04
2020
revised:
01
09
2020
accepted:
07
09
2020
pubmed:
15
9
2020
medline:
3
7
2021
entrez:
14
9
2020
Statut:
ppublish
Résumé
Metronidazole and its derivatives are widely used for the treatment of amoebiasis. However, metronidazole is considered as the standard drug but it has many side effects. The present study describes the synthesis of a series of metronidazole based thiazolidinone analogs via Knoevenagel condensation of 4-[2-(2-methyl-5-nitro-1H-imidazole-1-yl)ethoxy]benzaldehyde 1 with various thiazolidinone derivatives 2-14 to get the new scaffold (15-27) having better activity and lesser toxicity. Six compounds have shown better efficacy and lesser cytotoxicity than the standard drug metronidazole towards HM1: IMSS strain of Entamoeba histolytica. These compounds may combat the problem of drug resistance and might be effective in identifying potential alternatives for future drug discovery against EhOASS.
Identifiants
pubmed: 32927029
pii: S0960-894X(20)30660-0
doi: 10.1016/j.bmcl.2020.127549
pii:
doi:
Substances chimiques
Amebicides
0
Protozoan Proteins
0
Thiazolidines
0
Metronidazole
140QMO216E
Sulfatases
EC 3.1.6.-
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
127549Informations de copyright
Copyright © 2020 Elsevier Ltd. All rights reserved.