Title: 5-(thien-2-yl) uracil analogs: 5-(5-methylthien-2-yl)-2'-deoxyuridine, 5-(5-thien-2-yl)-2'-deoxyuridine, and 5-(5-bromothien-2-yl)-2'-deoxyuridine
Authors: Creuven, I ×
Norberg, B
Olivier, A
Evrard, C
Evrard, G
Wigerinck, P
Herdewijn, Piet
Durant, F #
Issue Date: Nov-1996
Publisher: Plenum publ corp
Series Title: Journal of chemical crystallography vol:26 issue:11 pages:777-789
Abstract: Crystal structures of 5-(5-methylthien-2-yl)-2'-deoxyuridine (I), 5-(5-thien-2-yl)-2'-deoxyuridine (II) and 5-(5-bromothien-2-yl)-2'-deoxyuridine (III) have been obtained from data collected on a four-circle Enraf-Nonius diffractometer (CAD-4 system). Space group, unit/cell parameters and final R indices are: I, monoclinic, P2(1), a = 9.105(2), b = 20.819(2), c = 7.932(2) Angstrom, beta = 98.79(2)degrees, R = 5.7%; II, monoclinic, P2(1), a = 8.720(4), b = 20.793(4), c = 7.884(4) Angstrom, beta = 95.06(2)degrees, R = 5.8%; III, monoclinic, p2(1), a = 9.260(2), b = 41.655(7), c = 7.926(2) Angstrom, beta = 97.996(13)degrees, R = 9.4%. Structural properties of the title compounds are compared with those of 5-(5-chlorothien-2-yl)-2'-deoxyuridine (IV) previously reported in order to explain their affinity for HSV-1 thymidine kinase and their eventual interaction with viral DNA polymerase. The main structural features observed are the coplanarity of the uracil and thienyl cycles stabilized by a S-O intramolecular interaction and the formation of dimeric intermolecular H bonds between two uracil moieties.
ISSN: 1074-1542
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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