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Supramolecular solid-state structure, potential energy surfaces and evaluation of antiproliferative effect of 2-benzothiazolylhydrazone derivatives in vitro

The in situ condensation reaction of 2- hydrazinobenzothiazole with salicylaldehyde, 3, 4-dihydroxybenzaldehyde, 2, 4- dihydroxybenzaldehyde, 2, 5-dihydroxybenzaldehyde, 2, 3-dihydroxybenzaldehyde, 2-hydroxy-1- naphthaldehyde, 2-methoxy-1-naphthaldehyde, 4-methoxy-1-naphthaldehyde and 6-methoxy-2- naphthaldehyde produced 9 hydrazone Schiff bases (L1–L9, respectively) which were identified and characterized by elemental analysis, IR and NMR spectroscopy. The crystal and molecular structures of four Schiff bases (L1, L7–L9) have been determined by the single-crystal X-ray diffraction method confirming the imino form of L1 and the amino tautomeric form of L7–L9 compounds. Molecular structure analysis also confirmed that reported compounds are E-isomers relative to exo C=N imino bond. The Nhydrazino–H group of amino tautomers forms Nhydrazino– HNthiazolyl intermolecular hydrogen bonds shaping molecules into R22(8) rings, while imino tautomer of L1 forms C(4) infinite helical chains via Nthiazolyl–H...Nhydrazino type of intermolecular hydrogen bond. The methoxy group(L7–L9) further shaped these primary supramolecular synthons into different supramolecular arrangements via C–H...O, C–H...N and C–H...S intermolecular hydrogen bonds. The role of aryl substituents in the shaping and stabilization of supramolecular architectures of L1, L7–L9 is supported by quantum chemical calculations. Strong antiproliferative effects on tumor cells and cytotoxic effects on fibroblasts are shown for all ligands L1–L9 with exception of L6 and L7 that had no effect on fibroblast cells.

Schiff base ligands, hydrazones, benzothiazoles, antiproliferative activity

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