Molecules 2012, 17(4), 4717-4732; doi:10.3390/molecules17044717
Article

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

Maha S. Al-Mutairi 1 , Ebtehal S. Al-Abdullah 1 , Mogedda E. Haiba 1,2 , Mohammed A. Khedr 3  and Wafaa A. Zaghary 1,3,* email
1 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia 2 Department of Medicinal Chemistry, National Research Center, Dokki, Cairo 12622, Egypt 3 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Helwan University, Ain Helwan, Cairo 11795, Egypt
* Author to whom correspondence should be addressed.
Received: 14 February 2012; in revised form: 9 April 2012 / Accepted: 13 April 2012 / Published: 23 April 2012
(This article belongs to the Section Medicinal Chemistry)
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Abstract: 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.
Keywords: tetrahydronaphthalene; pyridine; glycoside; cytotoxic; molecular docking

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MDPI and ACS Style

Al-Mutairi, M.S.; Al-Abdullah, E.S.; Haiba, M.E.; Khedr, M.A.; Zaghary, W.A. 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 2012, 17, 4717-4732.

AMA Style

Al-Mutairi MS, Al-Abdullah ES, Haiba ME, Khedr MA, Zaghary WA. 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. 2012; 17(4):4717-4732.

Chicago/Turabian Style

Al-Mutairi, Maha S.; Al-Abdullah, Ebtehal S.; Haiba, Mogedda E.; Khedr, Mohammed A.; Zaghary, Wafaa A. 2012. "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 17, no. 4: 4717-4732.

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