2001
DOI: 10.1021/jm010226s
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Synthesis and Antiviral Activity of Novel 5-(1-Cyanamido-2-haloethyl) and 5-(1-Hydroxy(or methoxy)-2-azidoethyl) Analogues of Uracil Nucleosides

Abstract: A new class of 5-(1-cyanamido-2-haloethyl)-2′-deoxyuridines (4-6) and arabinouridines (7, 8) were synthesized by the regiospecific addition of halogenocyanamides (X-NHCN) to the 5-vinyl substituent of the respective 5-vinyl-2′-deoxyuridine (2) and 2′-arabinouridine (3). Reaction of 2 with sodium azide, ceric ammonium nitrate, and acetonitrile-methanol or water afforded the 5-(1-hydroxy-2-azidoethyl)-( 10) and 5-(1-methoxy-2-azidoethyl)-2′-deoxyuridines (11). In vitro antiviral activities against HSV-1-TK + (KO… Show more

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Cited by 24 publications
(29 citation statements)
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“…None of the compounds were markedly inhibitory against HSV-1 strains (KOS, E-377), and HSV-2, which is not surprising in view of the inactivity of various other acyclic pyrimidine nucleosides [74,76,77]. In contrast, compounds 39-47 exhibited activity against VZV (EC 50 = 2.4 -52 µM), as compared to the reference drug ACV (EC 50 = 2.6 µM) [73]. Intriguingly, the acyclic derivatives of 5-(1-azido-2-haloethyl)uracil (39)(40)(41)(42)(43)(44)(45)(46)(47) also proved inhibitory to HCMV.…”
Section: Evaluation Of Acyclic Derivatives Containing 5-(1-azido-2-hamentioning
confidence: 88%
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“…None of the compounds were markedly inhibitory against HSV-1 strains (KOS, E-377), and HSV-2, which is not surprising in view of the inactivity of various other acyclic pyrimidine nucleosides [74,76,77]. In contrast, compounds 39-47 exhibited activity against VZV (EC 50 = 2.4 -52 µM), as compared to the reference drug ACV (EC 50 = 2.6 µM) [73]. Intriguingly, the acyclic derivatives of 5-(1-azido-2-haloethyl)uracil (39)(40)(41)(42)(43)(44)(45)(46)(47) also proved inhibitory to HCMV.…”
Section: Evaluation Of Acyclic Derivatives Containing 5-(1-azido-2-hamentioning
confidence: 88%
“…Reaction of 5-vinyl-2'-deoxyuridine with sodium azide, ceric ammonium nitrate, and acetonitrile-methanol or water afforded the 5-(1-hydroxy-2-azidoethyl)-(37) and 5-(1-methoxy-2-azidoethyl)-(38) analogs of 2'-deoxyuridine (Scheme 5) [73].…”
Section: Evaluation Of 5-(1-cyanamido-2-haloethyl)-and 5-(1-hydroxy(omentioning
confidence: 99%
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“…Dideoxynucleosides (ddNs) lack both 2'-and 3'-hydroxyl groups, and can inhibit the replication of the human immunodeficiency virus (HIV), which is the etiologic agent of the acquired immunodeficiency syndrome (AIDS). Several ddNs and their analogs are currently used as a treatment for HIV infection either singly or in a combination therapy of homo-and heterodimeric derivatives of ddNs for increased antiviral effects [1][2][3][4]. ddNs are also important in treatment of other viral infections and in cancer chemotherapy.…”
Section: Introductionmentioning
confidence: 99%