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Regioselective synthesis of fused ring heterocyclic derivatives of ketene aminals and their biological activities
Author(s) -
Yaqub Muhammad,
Batool Javeria,
Mahmood Khalid,
Ashraf Abida,
Perveen Ruqayia,
Shafiq Zahid
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4014
Subject(s) - chemistry , regioselectivity , aminal , ketene , moiety , ring (chemistry) , imidazole , stereochemistry , thiazole , combinatorial chemistry , aryl , organic chemistry , catalysis , alkyl
A regioselective and convenient methodology was developed to synthesize heterocyclic derivatives, bearing imidazole, piperidines, and azepines rings. The N ‐arylnitrones derived from 3‐formylchromones were selected to react with heterocyclic ketene aminal to furnish the structurally attractive and pharmacologically important fused ring heterocycles. The N ‐arylnitrone moiety of 3‐formylchromone was used to activate the formyl group for regioselective fused ring heterocycles synthesis, whereas, the effect of substituents at aryl functionality of nitrones were studied to improve the yield of target fused ring heterocyclic products. The synthesized compounds (10‐12) were evaluated for their in vitro cytotoxic and antifungal influences. In cytotoxic (brine shrimp lethality) assay, compound 11e was found to be active with LD 50 = 4.1 × 10 −6 μg/mL.