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

Molecules

Maha S. Al-Mutairi¹  Ebtehal S. Al-Abdullah¹  Mogedda E. Haiba¹  Mohammed A. Khedr² 

[1] Department of Pharmaceutical Chemistry, Faculty of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia;Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Helwan University, Ain Helwan, Cairo 11795, Egypt

关键词: tetrahydronaphthalene;    pyridine;    glycoside;    cytotoxic;    molecular docking;   

DOI  :  10.3390/molecules17044717

来源: mdpi

【 摘 要 】

A facile, convenient and high yielding synthesis of novel S-glycosides and N-glycosides incorporating 1,2,3,4-tetrahydronaphthalene and or 1,2-dihydropyridines moieties has been described. The aglycons 2, 4, and 7 were coupled with different activated halosugars in the presence of basic and acidic medium. The preliminary in-vitro cytotoxic evaluation revealed that compounds 3c, 3f, 5c and 7b 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.

【 授权许可】

CC BY   
© 2012 by the authors; licensee MDPI, Basel, Switzerland.