Novel amides of mycophenolic acid and some heterocyclic derivatives as immunosuppressive agents.
IMPDH inhibition
Mycophenolic acid
amide derivatives
benzoxazole
heterocycles
Journal
Journal of enzyme inhibition and medicinal chemistry
ISSN: 1475-6374
Titre abrégé: J Enzyme Inhib Med Chem
Pays: England
ID NLM: 101150203
Informations de publication
Date de publication:
Dec 2022
Dec 2022
Historique:
entrez:
3
10
2022
pubmed:
4
10
2022
medline:
5
10
2022
Statut:
ppublish
Résumé
The group of 18 new amide derivatives of mycophenolic acid (MPA) and selected heterocyclic amines was synthesised as potential immunosuppressive agents functioning as inosine-5'-monophosphate dehydrogenase (IMPDH) uncompetitive inhibitors. The synthesis of 14 of them employed uronium-type activating system (TBTU/HOBt/DIPEA) while 4 of them concerned phosphonic acid anhydride method (T3P/Py) facilitating amides to be obtained in moderate to excellent yields without the need of phenolic group protection. Most of optimised protocols did not require complicated reaction work-ups, including chromatographic, solvent-consuming methods. The biological activity assay was performed on the T-Jurkat cell line and peripheral mononuclear blood cells (PBMCs) which are both dedicated for antiproliferative activity determination. Each of designed derivatives was characterised by reduced cytotoxicity and benzoxazole analogue (
Identifiants
pubmed: 36189734
doi: 10.1080/14756366.2022.2127701
pmc: PMC9542285
doi:
Substances chimiques
Amides
0
Amines
0
Anhydrides
0
Benzoxazoles
0
Enzyme Inhibitors
0
Immunosuppressive Agents
0
Solvents
0
Inosine
5A614L51CT
IMP Dehydrogenase
EC 1.1.1.205
Mycophenolic Acid
HU9DX48N0T
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
2725-2741Références
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