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

✍ Scribed by Mónica A. Raviolo; Patricia A.M. Williams; Susana B. Etcheverry; Oscar E. Piro; Eduardo E. Castellano; Maria S. Gualdesi; Margarita C. Briñón

• Book ID: 103838624
• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 539 KB
• Volume: 970
• Category: Article
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2010.02.032

✦ Synopsis

a b s t r a c t 3 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) 2 C@O], prepared by the reaction of zidovudine with carbonyldiimidazole. The carbonate compound, C 21 H 24 N 10 O 9 , crystallizes in the tetragonal space group P4 1 2 1 2 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.