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Diastereoselective synthesis of pyrrolo[1, 2‐c]imidazoles using chiral thiohydantoins, malononitrile, and aldehydes and evaluation of their antioxidant and antibacterial activities
Author(s) -
Mollanejad Khadijeh,
Asghari Sakineh,
Jadidi Khosrow
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.3762
Subject(s) - chemistry , malononitrile , dpph , antibacterial activity , ring (chemistry) , alkyl , antioxidant , organic chemistry , bromine , cyanoacetamide , medicinal chemistry , bacteria , catalysis , biology , genetics
Diastereoselective synthesis of pyrrolo[1,2‐c]imidazoles is reported from three‐component reaction of chiral thiohydantoins, aldehydes, and malononitrile in the presence of NEt 3 . The antioxidant properties of the obtained products were evaluated by 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) radical scavenging assay. Among the products, compound 4l possessing NH 2 and NH groups and bromine atom at 4‐position of the aromatic ring displayed the highest antioxidant activity (90%). Also, their antibacterial activities were explored against gram‐positive and gram‐negative bacteria using disc diffusion method. Among the synthesized compounds, 4a with chlorine atom at para position of the aromatic ring, and methyl group (the smallest alkyl group) at 7‐position, displayed the best antibacterial activity against the tested gram‐positive bacteria.