Synthesis, molecular structure and physicochemical properties of bis(3’-azido-3’-deoxythymidin-5’-yl) carbonate

MÓNICA A. RAVIOLO, PATRICIA A.M. WILLIAMS, SUSANA B. ETCHEVERRY, OSCAR E. PIRO, EDUARDO E. CASTELLANO, MARIA S. GUALDESI, MARGARITA C. BRIÑÓN

JOURNAL OF MOLECULAR STRUCTURE THEOCHEM

ELSEVIER SCIENCE BV

Año: 2010 vol. 970 p. 59 - 65

0166-1280

30-Azido-30-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)2C=O], prepared by the reaction of zidovudine with carbonyldiimidazole. The carbonate compound,C21H24N10O9, crystallizes in the tetragonal space group P41212 with a = b = 15.284(1), c = 21.695(1) 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.