Peculiar reaction behavior of 1,3-oxathiolan-5-one toward various reagents: Molecular modeling studies and in vitro antioxidant and cytotoxicity evaluation

Chemical reactivity of 2-methyl-2-phenyl-1,3-oxathiolan-5-one (1) toward various reagents such as hydroxyaldehyde, ketone, α , β unsaturated carbonyl compounds, heterocyclic amine, hydrazine, and hydrazide to give unpredicative opened and fused heterocyclic systems was investigated. Moreover, treatm...

Full description

Saved in:
Bibliographic Details
Published in:Synthetic communications 2017-03, Vol.47 (6), p.566-580
Main Authors: Hamama, Wafaa S., Ibrahim, Mona E., Ghaith, Eslam A., Zoorob, Hanafi H.
Format: Article
Language:English
Subjects:
Cytotoxic activity (in vitro)
Cytotoxicity
heterocyclization
molecular modeling
oxathiolane
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Chemical reactivity of 2-methyl-2-phenyl-1,3-oxathiolan-5-one (1) toward various reagents such as hydroxyaldehyde, ketone, α , β unsaturated carbonyl compounds, heterocyclic amine, hydrazine, and hydrazide to give unpredicative opened and fused heterocyclic systems was investigated. Moreover, treatment of compound 1 with bromoester to afford the respective fused system, 2-methyl-2-phenylfuro[3,2-d][1,3]oxathiol-5(6H)-one (6) was implemented. Besides, 1 H- 1 H nuclear overhauser effect spectroscopy was used for full confirmation of the compound 19. In addition, the density functional theory modeling study outcomes were discussed and all of the new synthesized compounds were evaluated as antioxidants and cytotoxicity assay against hepatocellular carcinoma cell line.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2016.1276190