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

<p>Chemical reactivity of 2-methyl-2-phenyl-1,3-oxathiolan-5-one (<b>1</b>) 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 <b>1</b> with bromoester to afford the respective fused system, 2-methyl-2-phenylfuro[3,2-d][1,3]oxathiol-5(6<i>H</i>)-one (<b>6</b>) was implemented. Besides, ¹H–¹H nuclear overhauser effect spectroscopy was used for full confirmation of the compound <b>19</b>. 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.</p

Convenient synthesis, antimicrobial evaluation and molecular modeling of some novel quinoline derivatives

<p><i>α, β</i>-Unsaturated carbonyl compounds <b>2a, 2b, 3,</b> and <b>4</b> were synthesized by the Knoevenagel condensation between 2-substituted quionoline-3-carboxaldehyde <b>1a</b> and/or <b>1b</b> with active methylene compounds. In addition, the synthesis of azlactone is achieved starting from <b>1a</b> and <i>N</i>-acetylglycine. Synthesis of pyridine, pyrene, and pyrimidine derivatives <b>6</b>–<b>8</b> were accomplished via one-pot multicomponent reaction of <b>1b</b> with acetyl acetone, malononitrile, and ammonium acetate; acetophenone, malononitrile, and NaOH; or acetyl acetone and urea in acidic medium. The new synthesized compounds showed good antimicrobial activities. The DFT calculations have been used to predict the electronic properties of the studied compounds.</p