Intensified Microwave-Assisted N-Acylation Procedure – Synthesis and Activity Evaluation of TRPC3 Channel Agonists with a 1,3-Dihydro-2H-benzo[d]imidazol-2-one Core

Abstract Upon controlled microwave heating and using cyanuric chloride as a coupling reagent, an efficient amidation procedure for the synthesis of 1,3-dihydro-2 H -benzo[ d ]imidazol-2-one-based agonists of TRPC3/6 ion channels has been developed. Compared to the few conventional protocols, a drast...

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Bibliographic Details
Published in:Synlett 2017-04, Vol.28 (6), p.695-700
Main Authors: Guedes de la Cruz, Gema, Svobodova, Barbora, Lichtenegger, Michaela, Tiapko, Oleksandra, Groschner, Klaus, Glasnov, Toma
Format: Article
Language:English
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Summary:Abstract Upon controlled microwave heating and using cyanuric chloride as a coupling reagent, an efficient amidation procedure for the synthesis of 1,3-dihydro-2 H -benzo[ d ]imidazol-2-one-based agonists of TRPC3/6 ion channels has been developed. Compared to the few conventional protocols, a drastic reduction in processing time from ca. 2 days down to 10 minutes was achieved accompanied by significantly improved product yields. The robustness of the method was confirmed by 18 additional examples including aromatic, aliphatic, and heterocyclic amines and acids. The obtained agonists were screened for biological activity at 1 μM concentration and few structure–activity relations have been established.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1589472