Heterocycles in the 5-position of 2'-deoxyuridine

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Synthesis of 8-mercapto-2',3'-dideoxyadenosine and 8-mercapto-2',3'-dideoxyinosine

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5-(thien-2-yl)-2'-deoxyuridine - a new and potent inhibitor of herpes-simplex virus type-1 replication

5-(Thien-2-yl)-2'-deoxyuridine, synthesized by coupling of 5-iodo-2'-deoxyuridine with 2-trimethylstannylthiophene in the presence of a Pd catalyst, shows potent anti-HSV-1 activity in vitro.status: publishe

Synthesis of thymidine from 5-iodo-2'-deoxyuridine

A simple, high yield synthesis of thymidine from 5-iodo-2'-deoxyuridine is described, using tetramethyltin and tetrakis(triphenylphosphine)palladium(0) in hexamethylphoshoric triamide. Likewise, 5-phenyl- and 5-vinyl-2'-deoxyuridine can be obtained, and through reduction of the latter the 5-ethyl analogue is also at hand.status: publishe

5-(5-Bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothien-2-yl)-2'-deoxyuridine are equipotent to (E)-5-(2-bromovinyl)-2'-deoxyuridine in the inhibition of herpes simplex virus type I replication

2'-Deoxyuridines with a five-membered heterocyclic substituent in the 5-position were synthesized by palladium-catalyzed coupling reactions of 5-iodo-2'-deoxyuridine with the activated heteroaromatics. Further modification of the compound with the 5-thien-2-yl substituent gave 5-(5-bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothienyl-2-yl)-2'-deoxyuridine. Both compounds show potent and selective activity against herpes simplex virus type 1 and varicella-zoster virus.status: publishe

3'-(1,2,3-Triazol-1-yl)-2',3'-dideoxythymidine and 3'-(1,2,3-triazol-1-yl)-2',3'-dideoxyuridine

Cycloaddition of different acetylenic compounds on the azido function of 3′‐azido‐2′,3′‐dideoxythymidine and 3′‐azido‐2′,3′‐dideoxyuridine afforded products with a 1,2,3‐triazol‐1‐yl substituent in the 3′‐position. In contrast with the parent compounds, these triazolyl derivatives had no appreciable activity against human immunodeficiency virus (HIV‐1). Copyright © 1989 Journal of Heterocyclic Chemistrystatus: publishe

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

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.status: publishe

Synthesis of thymidine analogs with a cyanoimido substituent

The synthesis of thymidine analogues with a N-cyanomido substituent in the 3'- or 5'- position is described.status: publishe