Synthesis, Molecular Docking and Preliminary in-Vitro Cytotoxic Evaluation of Some Substituted Tetrahydro-naphthalene (2',3',4',6'-Tetra-O-Acetyl-β-D-Gluco/-Galactopyranosyl) Derivatives

Abstract

A facile, convenient and high yielding synthesis of novel <em>S</em>-glycosides and <em>N</em>-glycosides incorporating 1,2,3,4-tetrahydronaphthalene and or 1,2-dihydropyridines moieties has been described. The aglycons <strong>2</strong>, <strong>4</strong>, and <strong>7</strong> were coupled with different activated halosugars in the presence of basic and acidic medium. The preliminary <em>in-vitro</em> cytotoxic evaluation<strong> </strong>revealed that compounds <strong>3c</strong>, <strong>3f</strong>, <strong>5c</strong> and <strong>7b</strong> show promising activity. A molecular docking study was performed against tyrosine kinase (TK) (PDB code: 1t46) by Autodock Vina. The docking output was analyzed and some compounds have shown hydrogen bond (H-B) formation with reasonable distances ranged from 2.06 A° to 3.06 A° with Thr 670 and Cys 673 residues found in the specified pocket. No hydrogen bond was observed with either Glu 640 nor Asp 810 residues, as was expected from pdbsum.

Keywords

• tetrahydronaphthalene
• pyridine
• glycoside
• cytotoxic
• molecular docking