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Synthesis, crystal structure and DNA binding interactions of ethyl 2-(2-acetamidothiazol-4-yl) acetate: Theoretical and experimental investigations

Z. Iqbal,Z. Ashraf,M. Abas,M. Tahir,Erum Jabeen,R. Z. Paracha,Maryum Nisar,Safeer Ahmad

Published 2019 in Journal of Molecular Structure

ABSTRACT

Abstract The present study describes the efficient synthesis, structural characterization and DNA binding interactions of ethyl 2-(2-acetamidothiazol-4-yl)acetate 2. Theoretically and experimentally determined bond lengths, angles and DNA binding interactions are compared. The chemical structure of the synthesized compound 2 was confirmed by spectral data and single crystal X-ray diffraction. The presence of –NH signal at 12.16 ppm in 1HNMR spectrum and carbonyl carbon at 170.5 ppm in 13CNMR spectrum confirmed the formation of ethyl 2-(2-acetamidothiazol-4-yl)acetate 2. The bond lengths and angles calculated theoretically are in good agreement with experimentally determined values. Molecular docking studies of synthesized compound 2 against five different DNA structures were performed to check its binding affinity with these targets. It was found that compound 2 binds well with DNA (PDB 1BPX ) having binding energy value −5.7 kcal/mol. The DNA binding interactions was also determined experimentally by spectrophotometric and electrochemical methods. The results showed that compound 2 binds with DNA through intercalation and groove binding which reflected the mixed binding mode. The binding constants (Kb) calculated from these results are 1.45 × 103 M−1 (UV–Vis spectroscopy), 1.41 × 103 M−1 (Fluorescence spectroscopy) and 1.39 × 103 M-1 (Cyclic voltammetry) also revealed strong binding. Based upon our results it was proposed that the synthesized compound 2 may act as a lead structure to design more potent antitumor agents.

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