Three-component Castagnoli-Cushman reaction with ammonium acetate delivers 2-unsubstituted isoquinol-1-ones as potent inhibitors of poly(ADP-ribose) polymerase (PARP).
Acetates
/ chemistry
Amino Acid Sequence
Antineoplastic Agents
/ chemistry
Binding Sites
DNA Damage
/ drug effects
Drug Screening Assays, Antitumor
Humans
NAD
/ metabolism
Phthalazines
/ pharmacology
Piperazines
/ pharmacology
Poly(ADP-ribose) Polymerase Inhibitors
/ chemistry
Poly(ADP-ribose) Polymerases
/ metabolism
Protein Binding
Protein Conformation
Quinolones
/ chemistry
Structure-Activity Relationship
1-oxo-3,4-dihydroisoquinoline-4-carboxamides
Castagnoli-Cushman reaction
NAD+ mimetics
PARP1/2 selectivity
druglikeness
poly(ADP-ribose) polymerase
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 2021
Dec 2021
Historique:
entrez:
31
8
2021
pubmed:
1
9
2021
medline:
22
9
2021
Statut:
ppublish
Résumé
An earlier described three-component variant of the Castagnoli-Cushman reaction employing homophthalic anhydrides, carbonyl compound and ammonium acetate was applied towards the preparation of 1-oxo-3,4-dihydroisoquinoline-4-carboxamides with variable substituent in position 3. These compounds displayed inhibitory activity towards poly(ADP-ribose) polymerase (PARP), a clinically validated cancer target. The most potent compound (PARP1/2 IC
Identifiants
pubmed: 34461785
doi: 10.1080/14756366.2021.1969386
pmc: PMC8409965
doi:
Substances chimiques
Acetates
0
Antineoplastic Agents
0
Phthalazines
0
Piperazines
0
Poly(ADP-ribose) Polymerase Inhibitors
0
Quinolones
0
NAD
0U46U6E8UK
Poly(ADP-ribose) Polymerases
EC 2.4.2.30
ammonium acetate
RRE756S6Q2
olaparib
WOH1JD9AR8
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
1916-1921Références
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