2′-Azido-2′,3′-dideoxythymidine: Synthesis and crystal structure of a 2′-substituted dideoxynucleoside
A. van Aerschot
1
,
Dirk G. Everaert
2
,
G. Gosselin
3
,
O. Peeters
2
,
N. Blaton
2
,
C. De Ranter
2
,
J.L. Imbach
3
,
Jan Balzarini
1
,
E. De Clercq
1
,
Piet Herdewijn
1
3
Université des Sciences et Techniques du Languedoc, Laboratoire de Chimie Bio-Organique, Montpellier, France
|
Publication type: Journal Article
Publication date: 1990-12-01
scimago Q1
wos Q1
SJR: 1.195
CiteScore: 7.3
Impact factor: 4.0
ISSN: 01663542, 18729096
PubMed ID:
2088211
Pharmacology
Virology
Abstract
1-(2-Azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)thymine (2'-N3ddThd) was synthesized from 1-(5-O-trityl-2,3-anhydro-beta-D-lyxofuranosyl)thymine by two different procedures. Method A prepared the title compound by opening of the oxirane ring with LiEt3BH followed by mesylation of the 2'-hydroxyl function, introduction of the 2'-azido substituent and deblocking of the 5'-function. In method B nucleophilic opening of 3'-deoxy-5'-O-(tert-butyldimethylsilyl)-5-methyl-2,2'-anhydrouridine+ ++ was carried out with sodium azide in hexamethylphosphoramide in the presence of benzoic acid. Single X-ray crystallographic studies indicated a solid state conformation (3T2), which was opposite to that of the A form of AZT (2T3) but closely resembled that of 1-(2-fluoro-2,3-dideoxy-beta-D-erythropentofuranosyl)thymine (2'-FddThd) (3T2) and of 3'-azido-2',3'-dideoxy-2,6-diaminopurine riboside (3'-N3ddDAP) (3T2). Whereas the latter displayed significant inhibitory activity against human immunodeficiency virus (HIV) replication, 2'-FddThd and 2'-N3ddThd were essentially inactive.
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van Aerschot A. et al. 2′-Azido-2′,3′-dideoxythymidine: Synthesis and crystal structure of a 2′-substituted dideoxynucleoside // Antiviral Research. 1990. Vol. 14. No. 6. pp. 357-369.
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van Aerschot A., Everaert D. G., Gosselin G., Peeters O., Blaton N., De Ranter C., Imbach J., Balzarini J., De Clercq E., Herdewijn P. 2′-Azido-2′,3′-dideoxythymidine: Synthesis and crystal structure of a 2′-substituted dideoxynucleoside // Antiviral Research. 1990. Vol. 14. No. 6. pp. 357-369.
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TY - JOUR
DO - 10.1016/0166-3542(90)90054-b
UR - https://doi.org/10.1016/0166-3542(90)90054-b
TI - 2′-Azido-2′,3′-dideoxythymidine: Synthesis and crystal structure of a 2′-substituted dideoxynucleoside
T2 - Antiviral Research
AU - van Aerschot, A.
AU - Everaert, Dirk G.
AU - Gosselin, G.
AU - Peeters, O.
AU - Blaton, N.
AU - De Ranter, C.
AU - Imbach, J.L.
AU - Balzarini, Jan
AU - De Clercq, E.
AU - Herdewijn, Piet
PY - 1990
DA - 1990/12/01
PB - Elsevier
SP - 357-369
IS - 6
VL - 14
PMID - 2088211
SN - 0166-3542
SN - 1872-9096
ER -
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BibTex (up to 50 authors)
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@article{1990_van Aerschot,
author = {A. van Aerschot and Dirk G. Everaert and G. Gosselin and O. Peeters and N. Blaton and C. De Ranter and J.L. Imbach and Jan Balzarini and E. De Clercq and Piet Herdewijn},
title = {2′-Azido-2′,3′-dideoxythymidine: Synthesis and crystal structure of a 2′-substituted dideoxynucleoside},
journal = {Antiviral Research},
year = {1990},
volume = {14},
publisher = {Elsevier},
month = {dec},
url = {https://doi.org/10.1016/0166-3542(90)90054-b},
number = {6},
pages = {357--369},
doi = {10.1016/0166-3542(90)90054-b}
}
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MLA
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van Aerschot, A., et al. “2′-Azido-2′,3′-dideoxythymidine: Synthesis and crystal structure of a 2′-substituted dideoxynucleoside.” Antiviral Research, vol. 14, no. 6, Dec. 1990, pp. 357-369. https://doi.org/10.1016/0166-3542(90)90054-b.