24514-32-7Relevant academic research and scientific papers
Central nervous system depressant effects of N3-substituted derivatives of deoxyuridine in mice
Kimura, Toshiyuki,Kuze, Jiro,Teraoka, Seisaku,Watanabe, Kazuhito,Tateoka, Yuji,Kondo, Shigemi,Ho, Ing Kang,Yamamoto, Ikuo
, p. 142 - 145 (1996)
N3-Substituted derivatives of deoxyuridine (1) were synthesized and their pharmacological effects were evaluated by intracerebroventricular (i.c.v.) injection in mice. Eleven derivatives, including the methyl (2), ethyl (3), propyl (4), allyl (5), butyl (6), benzyl (7), o, m and p-xylyls (8, 9, 10), α-phenylethyl (11) and phenacyl (12) derivatives, of I were prepared and their pharmacological effects were evaluated by using hypnotic activity, pentobarbital-induced sleep prolongation, spontaneous activity and motor incoordination as indices of central nervous system (CNS) depressant effects. At a dose of 2.0 μmol/mouse, the values of mean sleeping time induced by 7, 8, 9 and 10 were 23, 35, 29 and 30 min, respectively. Although the alkyl (2- 6) derivatives did not cause any hypnotic activity, some derivatives tested (3, 5, 6, 8-12) significantly prolonged the pentobarbital-induced sleeping time. When the CNS depressant effects of phenacyl substituted 1 were compared to that of other oxopyrimidine nucleosides, N3-phenacyluridine (13), N3- phenacylthymidine (14), N3-phenacyl-6-azauridine (15), compounds 12, 13 and 14 (1.0 μmol/mouse, i.c.v.) significantly decreased mouse spontaneous activity. Furthermore, 12-15 (1.0 μmol/mouse, i.c.v.) caused mouse motor incoordination. These results indicate that deoxyuridine derivatives have generally central depressant activity, and the benzyl and xylyl derivatives, but not alkyl derivatives, possess hypnotic activity.
Unexpected formation of 2′-deoxy-N3-(3,3,3-trifluoro-1-propenyl)uridine via a Michael-type addition to 3,3,3-trifluoropropyne
Chirakul, Panadda,Sigurdsson, Snorri Th.
, p. 6899 - 6901 (2003)
Reaction of 3,3,3-trifluoropropyne with 2′-deoxy-5-iodouridine under conditions that have previously been used to prepare 5-alkynyl-2′-deoxyuridine derivatives gave 2′-deoxy-N3-(3,3,3-trifluoro-1-propenyl)uridine. This unexpected alkylation is a result of a Michael-type addition of N3 on the pyrimidine base to the electron deficient trifluoropropyne.
Methylation study of ribonucleosides, deoxyribonucleosides, and 2′-O-methylribonucleosides with trimethylsulphonium hydroxide and trimethylsulphonium iodide. Influence of the 2′-hydroxy-groups on the reactivity of the base moieties of ribonucleosides
Yamauchi, Kiyoshi,Nakagima, Toru,Kinoshita, Masayoshi
, p. 2787 - 2792 (2007/10/02)
Methylations of the naturally occuring ribonucleoside (1), deoxyribonucleoside (2), and 2′-O-methylribonucleoside (3) were carried out using trimethylsulphonium hydroxide (Me3SOH) and trimethylsulphonium iodide (Me3Sl). The base moiety of (2) and (3) are more reactive than the corresponding base moiety of (1). The sites and extent of methylation of (2) are considerably different from those of (1), but are almost identical with those of (3). The reactivities of (1)-(3) are discussed in connection to an intramolecular interaction of the 2′-OH groups with the base moiety of (1). The methylating characteristics of Me 3SOH and Me3Sl are also described. The kinetics indicate an SN2 mechanism for methylation of nucleosides by Me 3S+ ions.
