[3+2] cycloaddition synthesis of new (nicotinonitrile‐chromene)‐based bis(pyrazole) hybrids as potential acetylcholinesterase inhibitors

A [3+2] cycloaddition protocol was used to prepare two series of (nicotinonitrile‐chromene)‐based bis(pyrazoles) in 82%–91% yields. The protocol involved the reaction of nitrilimines, which were generated in situ by the action of triethylamine on hydrazonoyl chlorides, with the respective (nicotinon...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 60; no. 1; pp. 156 - 160
Main Authors Mekky, Ahmed E. M., Sanad, Sherif M. H.
Format Journal Article
LanguageEnglish
Published Chichester, UK John Wiley & Sons, Inc 01.01.2023
Wiley
Wiley Subscription Services, Inc
Subjects
Chemistry
Chemistry, Organic
Cycloaddition
Free radicals
Physical Sciences
Pyrazole
Science & Technology
Triethylamine
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Summary:A [3+2] cycloaddition protocol was used to prepare two series of (nicotinonitrile‐chromene)‐based bis(pyrazoles) in 82%–91% yields. The protocol involved the reaction of nitrilimines, which were generated in situ by the action of triethylamine on hydrazonoyl chlorides, with the respective (nicotinonitrile‐chromene)‐based bis(enaminone). At the concentrations tested, bis(pyrazole) linked to 1‐(4‐methoxyphenyl) and 3‐acetyl units had the best acetylcholinesterase and DPPH‐free radical inhibitory activity. We reported herein the [3+2] cycloaddition synthesis of two series of (nicotinonitrile‐chromene)‐based bis(pyrazoles) as potential acetylcholinesterase and DPPH‐free radical inhibitors.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4590