5964-41-0Relevant academic research and scientific papers
New 3′-deoxythymidines bearing a nucleophilic 3′-substituent
Belostotskii,Keren-Yeshuah,Lexner,Hassner
, p. 93 - 101 (2001)
New potential cancer-driven as well as HIV-driven nucleoside heteroanalogs, such as 3′-thio- and 3′- as well as 5′-selenosubstituted thymidines, have been synthesized. We also report an effective method for the preparation of novel nucleoside derivatives, bis(deoxynucleoside) diselenides, in nearly quantitative yields. The North conformation is significantly populated in the conformational equilibrium for 3′-α-alkylthiothymidines.
Synthesis of acyclic bis-vinyl pyrimidines: A general route to d4T via metathesis
Ewing,Gla?on,Mackenzie,Postel,Len
, p. 941 - 945 (2007/10/03)
Unsaturated acyclic pyrimidine analogues, 1-{1-[1-(hydroxymethyl)prop-2-enyloxy]prop-2-enyl}uracil, 1-{1-[1-(hydroxymethyl)prop-2-enyloxy]prop-2-enyl}thymine and 1-{1-[1-(hydroxymethyl)prop-2-enyloxy]prop-2-enyl}cytosine having two asymmetric carbon atoms have been prepared in good yield starting from uridine and 5-methyluridine. The bis-vinyl thymine derivative underwent ring closure metathesis to give d4T, thus providing a novel synthesis of this compound.
A novel approach to unsaturated acyclic nucleoside analogues and the first synthesis of d4T by ring closure metathesis
Ewing, David,Gla?on, Virginie,Mackenzie, Grahame,Postel, Denis,Len, Christophe
, p. 3503 - 3505 (2007/10/03)
Novel unsaturated acyclic nucleoside analogues, 1-{1-[1-(hydroxymethyl)prop-2-enyloxy]prop-2-enyl}uracil, 1-{1-[1-(hydroxymethyl)prop-2-enyloxy]prop-2-enyl}thymine and 1-{1-[1-(hydroxymethyl)prop-2-enyloxy]prop-2-enyl}cytosine have been prepared in good yield from uridine and 5-methyluridine by periodate cleavage followed by a double Wittig reaction which introduces two vinyl groups. The thymine derivative underwent ring closure metathesis to give a novel synthesis of d4T.
Synthesis and evaluation of thymidine-5′-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase
Vanheusden, Veerle,Munier-Lehmann, Helene,Pochet, Sylvie,Herdewijn, Piet,Van Calenbergh, Serge
, p. 2695 - 2698 (2007/10/03)
A number of 2′- and 3′-modified thymidine 5′-O-monophosphate analogues were synthesized as potential leads for new anti-mycobacterial drugs. Evaluation of their affinity for Mycobacterium tuberculosis thymidine monophosphate kinase showed that a 2′-halogeno substituent and a 3′-azido function are the most favorable leads for further development of potent inhibitors of this enzyme.
Synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides by reaction of 5′-protected nucleoside 2′,3′-dimesylates with telluride dianion: A general route from cis vicinal diols to olefins
Clive, Derrick L. J.,Wickens, Philip L.,Sgarbi, Paulo W. M.
, p. 7426 - 7437 (2007/10/03)
2′,3′-Dimesylates of 5′-protected nucleosides are converted into the corresponding 2′,3′-didehydro2′,3′-dideoxy compounds by treatment with telluride dianion in the form of the sodium or lithium salt. The method is well-suited to the preparation of unsaturated nucleosides that can be converted into compounds that are believed to be useful in the treatment of AIDS. The deoxygenation is general for vicinal dimesylates that have, or may adopt, a synperiplanar conformation. With straight chain compounds the reaction is stereospecific. In some cases, similar, but slower, deoxygenations can be performed with selenide dianion.
