Enantiomerically Pure Phosphonated Carbocyclic 2'-Oxa-3'-Azanucleosides: Synthesis and Biological Evaluation

Molecules

Roberto Romeo³  Caterina Carnovale³  Salvatore V. Giofrè³  Giulia Monciino¹  Maria A. Chiacchio¹  Claudia Sanfilippo² 

[1] Dipartimento Scienze del Farmaco, Università di Catania, Viale A. Doria 6, 95125 Catania, Italy; E-Mails:;Istituto di Chimica Biomolecolare del CNR, Via P. Gaifami 18, 95126 Catania, Italy; E-Mail:;Dipartimento Scienze del Farmaco e Prodotti per la Salute, Università di Messina, Via S.S. Annunziata, 98168 Messina, Italy; E-Mail:

关键词: PCOANs;    N;    O-modified nucleosides;    antiretroviral;   

DOI  :  10.3390/molecules190914406

来源: mdpi

【 摘 要 】

Starting from enantiomeric pure 1-[(3S,5R)- and 1-[(3R,5S)-3-(hydroxymethyl)-2-methylisoxazolidin-5-yl]-5-methylpyrimidine-2,4(1H,3H)-diones (−)7a and (+)7b, obtained by lipase-catalyzed resolution, pure diethyl{[(3S,5R)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl]methyl}phosphonate (−)12a and diethyl{[(3R,5S)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl]methyl}phosphonate (+)12b have been synthesized. The obtained compounds showed no cytotoxic activity versus the U937 cell line in comparison with AZT, and were poorly able to inhibit HIV infection in vitro.

【 授权许可】

CC BY   
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