Archives

Synthesis and Characterization of New Molecule, 2-(Hydroxymethyl)-6-(4-((2-((E)-((3-Mercapto-5-Methyl-4H-1,2,4-Triazol-4-yl)Imino) Methyl)-4-Methoxyphenoxy) Methyl)-1H-1,2,3-Triazol-1-yl) Tetrahydro-2H-Pyran-3,4,5-Triol, and its Activity Against Anticance


Majed Jari Mohammed, Abdul Amir H. Kadhum, Hasan Hayder Mohammed and Adnan Ibrahim Mohammed
Abstract

The molecule ((2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-((2-((E)-((3-mercapto-5-methyl-4H-1,2,4-triazole-4-yl)imino)methyl)-4-methoxyphenoxy)methyl-1H-2,3-triazole-1-yl)tetraydro-2H-pyran-3,4,5-triol,10, based on D-glucose, was synthesized via two routes. The first routeis the reaction of 2-hydroxy-5-methoxy benzaldehyde 1 with propargyl bromide (3-bromoprop-1-yne) 2to afford propargyl ether(5-methoxy-2-(prop-2-yn-1-yloxy) benzaldehyde) 3; the second route is the reaction of B-D-glucose pentaacetate ((2R,3R,4S,5R,6R)-6-(acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate)4 with 33%HBr in glacial acetic acid to give glycosyl bromide (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate5,which was reacted with sodium azide to afford glycosyl azide(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate) 6. The reaction of 6 with 3 afforded the triazole derivative (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(4-((2-formyl-4-methoxy)methyl)-1H-1,2,3-triazole-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate)7. The triazole imine derivative (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(4-((2-(((3-mercapto-5-methyl-4H-1,2,4-tiazol-4-yl)imino)methyl)-4-methoxyphenoxy)methyl)-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate9was prepared from the reaction of7with4-amino-5-methyl-4H-1,2,4-triazole-3-thiol 8. Removal of the acetyl protecting groups from 9 afforded the desired molecule, 10, whose structure was examined by FTIR, 1HNMR, and 13CNMR spectroscopies.

Volume 11 | 03-Special Issue

Pages: 1949-1954