Title: Synthesis of Novel AZA-Analogues of Tiazofurin with 2-[5,5-bis(Hydroxymethyl)Pyrrolidin-2-yl] Framework as Sugar Mimic
Authors: Mironiuk-Puchalska, Ewa ×
Koszytkowska-Stawińska, Mariola
Sas, Wojciech
De Clercq, Erik
Naesens, Lieve #
Issue Date: Jan-2012
Publisher: Marcel Dekker
Series Title: Nucleosides, Nucleotides & Nucleic Acids vol:31 issue:1 pages:72-84
Abstract: The novel aza-analogues of tiazofurin (TZF) with 2-[5,5-bis(hydroxymethyl)pyrrolidin-2-yl] moiety, as sugar mimic, were synthesized from O,O-cyclohexylidene derivative of 4,4-bis(hydroxymethyl)-4-nitrobutanal in multi-gram scale. The synthetic route consisted of three stages: (i) the synthesis of corresponding derivative of 5,5-bis(hydroxymethyl)pyrrolidine-2-carbonitrile, (ii) the construction of ethyl thiazole-2-carboxylate part by the conversion of the pyrrolidine-2-carbonitrile into the N-trifluoroacetyl derivative followed by cyclocondensation with L-cysteine ethyl ester and then by dehydrogenation, and (iii) the final transformation of the ethyl thiazole-4-carboxylate into the aza-analogues of TZF. The TZF aza-analogues were evaluated for their antiviral activities in cell-culture-based assays.
ISSN: 1525-7770
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

Files in This Item:
File Description Status SizeFormat
2012005.pdf Published 222KbAdobe PDFView/Open


All items in Lirias are protected by copyright, with all rights reserved.

© Web of science