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

• Main Authors: Maha S. Al-Mutairi, Ebtehal S. Al-Abdullah, Mogedda E. Haiba, Mohammed A. Khedr, Wafaa A. Zaghary
• Format: Article
• Language: English
• Published: MDPI AG 2012-04-01
• Series: Molecules
• Subjects: tetrahydronaphthalene; pyridine; glycoside; cytotoxic; molecular docking
• Online Access: http://www.mdpi.com/1420-3049/17/4/4717

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.