Synthesis of Isomeric 3-Benzazecines Decorated with Endocyclic Allene Moiety and Exocyclic Conjugated Double Bond and Evaluation of Their Anticholinesterase Activity.
Acetylcholinesterase
/ metabolism
Alcohols
Alkadienes
Alkynes
Butyrylcholinesterase
/ chemistry
Cholinesterase Inhibitors
/ chemistry
Humans
Isoquinolines
Molecular Docking Simulation
Molecular Structure
Monoamine Oxidase
/ metabolism
Monoamine Oxidase Inhibitors
/ chemistry
Structure-Activity Relationship
Water
-ylidene derivatives
3-benzazecines
acetylcholinesterase
anti-cholinesterase activity
azacyclic allenes
butyrylcholinesterase
monoamine oxidase A and B screening
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
23 Sep 2022
23 Sep 2022
Historique:
received:
22
08
2022
revised:
17
09
2022
accepted:
19
09
2022
entrez:
14
10
2022
pubmed:
15
10
2022
medline:
18
10
2022
Statut:
epublish
Résumé
Transformations of 1-methoxymethylethynyl substituted isoquinolines triggered by terminal alkynes in alcohols were studied and new 3-benzazecine-containing compounds synthesized, such as 6-methoxymethyl-3-benzazecines incorporating an endocyclic C6-C8 allene fragment and the -ylidene derivatives 6-methoxymethylene-3-benzazecines. The reaction mechanisms were investigated and a preliminary in vitro screening of their potential inhibitory activities against human acetyl- and butyrylcholinesterases (AChE and BChE) and monoamine oxidases A and B (MAO-A and MAO-B) showed that the allene compounds were more potent than the corresponding -ylidene ones as selective AChE inhibitors. Among the allenes,
Identifiants
pubmed: 36234811
pii: molecules27196276
doi: 10.3390/molecules27196276
pmc: PMC9571408
pii:
doi:
Substances chimiques
Alcohols
0
Alkadienes
0
Alkynes
0
Cholinesterase Inhibitors
0
Isoquinolines
0
Monoamine Oxidase Inhibitors
0
Water
059QF0KO0R
propadiene
4AV0LZ8QKB
Monoamine Oxidase
EC 1.4.3.4
Acetylcholinesterase
EC 3.1.1.7
Butyrylcholinesterase
EC 3.1.1.8
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
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