Synthesis, Molecular Structure and Physicochemical Properties of Bis(3´-Azido-3´-Deoxythymidin -5-yl) Carbonate.

MÓNICA A. RAVIOLO ; PATRICIA A. WILLIAMS; SUSANA B. ETCHEVERRY; OSCAR E. PIRO; EDUARDO E. CASTELLANO; MARÍA S. GUALDESI; MARGARITA C. BRIÑÓN.

ELSEVIER SCIENCE BV

Año: 2010 vol. 970 p. 59 - 59

-0-Azido-3-0-deoxythymidine (zidovudine, AZT), a synthetic analog of natural nucleoside thymidine, has been used extensively in AIDS treatments. We report here the synthesis, X-ray crystal and molecular structure, NMR, IR and Raman spectra and the thermal behavior of a novel carbonate of AZT [(AZT–O)2CO], prepared by the reaction of zidovudine with carbonyldiimidazole. The carbonate compound,C21H24N10O9, crystallizes in the tetragonal space group P41212 with a = b = 15.284, c = 21.695 Å, and Z = 8 molecules per unit cell. It consists of two AZT moieties of closely related conformations which are bridged by a carbonyl group to adopt a folded Z-like shape.