An efficient carbodiimide-mediated synthesis and DNA-binding studies of novel 2-chloro/mercapto-quinoline-fused 1,3-thiazolidinones via one-pot three-component condensation

作者：Lamani Devappa S; Reddy K R Venugopala^*; Naik H S Bhojya; Naik H R Prakash; Naik L R

来源：Journal of Sulfur Chemistry, 2010, 31(1): 49-59.

DOI：10.1080/17415990903295678

• quinoline
• DCC
• thiazolidinones
• one-pot synthesis
• DNA binding
• viscosity measurements
• thermal denaturation

A new and efficient method for the preparation of 2-(2-chloroquinolin-3-yl)-3-(4-methylphenyl)-1, 3-thiazolidin-4-one derivatives has been assembled by DCC:-mediated three-component one-pot reaction of amine, aldehyde, and mercaptoacetic acid. The final compounds were obtained in quantitative yields within 50min. The synthesized compounds were characterized by elemental analysis, FT-IR, 1H-NMR, and mass spectral data. The selected compounds were studied for interaction with calf thymus DNA by electronic spectra, viscosity measurements as well as thermal denaturation studies. On binding to DNA, the absorption spectrum underwent bathochromic and hypochromic shifts. The binding constant (Kb) had a value of 5.3x105M-1 for 2a and 5.8x105M-1 for 3a. The viscosity measurements indicated that the viscosity of sonicated rod-like DNA fragments increased.

• 出版日期2010