101552-16-3Relevant academic research and scientific papers
Synthesis and anti-HIV activity of triazolo-fused, medium-sized cyclic nucleoside analogs prepared by an intramolecular huisgen 1,3-dipolar cycloaddition
Sun, Jingbo,Liu, Rongwang,Fu, Qiang,Zang, Jian,Tao, Qiangqiang,Wu, Jinchang,Zhu, Hui
, p. 733 - 743 (2014/06/09)
Medium-sized cyclic nucleosides containing a fused triazole ring were synthesized via intramolecular Huisgen 1,3-dipolar cycloadditon reaction. 2′,3′-seco-Uridine was employed as the key intermediate for the introduction of azido and alkynyl moieties in the defined positions of the reaction precursors. The cycloaddition reactions were achieved in high yields by heating the precursor in refluxing toluene. The uracil base in these target compounds was successfully transformed to the corresponding cytosine. The synthesized compounds were evaluated in a MAGI assay for their anti-HIV activities, and in a H9 T lymphocytes assay for their cell toxicities. Copyright
Synthesis and reactions of some 3',4'-unsaturated 2',3'- secouridine analogues
Kikuchi, Shinya,Maekawa, Tomohiro,Minamoto, Katsumaro,Tanigawa, Keizo
, p. 1365 - 1372 (2007/10/03)
2',3'-Dibromo-2',3'-dideoxy-5'-O-trityl-2',3'-secouridine (8) with sdKF gave the 3',4'-didehydro-2,2'-anhydro nucleoside 9, which was deprotected to 10. Hydrolysis of 9 gave 3',4'-didehydro-3'-deoxy-5'-O-trityl-2',3'- secouridine (11a). Similarly, compoun
Regioselective Transformations of 2',3'-Seconucleosides into Anhydro Structures and Chiral Crown Ethers
Skaric, Vinko,Caplar, Vesna,Skaric, Durdica,Zinic, Mladen
, p. 493 - 506 (2007/10/02)
Intramolecular cyclisation of properly protected and activated derivatives of 2',3'-secouridine (= 1--ethyl>uracil; 1) provided access to the 2,2'-, 2,3'-, 2,5'-, 2',5'-, 3',5'-, and 2',3-anhydro-2',3'-secouridines 5, 16, 17, 26, 28 and 31, respectively (Schemes 1-3).Reaction of 2',5'-anhydro-3'-O-(methylsulfonyl)- (25) and 2',3'-anhydro-5'-O-(methylsulfonyl)-2',3'-secouridine (32) with CH2Cl2 in the presence of 1,8-diazabicycloundec-7-ene generated the N(3)-methylene-bridged bis-uridine structure 37 and 36, respectively (Scheme 3).Novel chiral 18-crown-6 ethers 40 and 44, containing a hydroxymethyl and a uracil-1-yl or adenin-9-yl as the pendant groups in a 1,3-cis relationship, were synthesized from 5'-O-(triphenylmethyl)-2',3'-secouridine (2) and 5'-O,N6-bis(triphenylmethyl)-2',3'-secoadenosine (41) on reaction with 3,6,9-trioxaundecane-1,11-diyl bis(4-toluenesulfonate) and detritylation of the thus obtained (triphenylmethoxy)methyl compound 39 and 43, respectively (Scheme 4).
NUCLEOSIDE ANALOGUES WITH A 1,4-DIOXANE, 1,4-OXATHIANE OR 1,4-OXAZINE RING STRUCTURE AS THE CARBOHYDRATE FRAGMENT
Aerschot, Arthur Van,Janssen, Gerard,Herdewijn, Piet
, p. 769 - 777 (2007/10/02)
Pyrimidine and purine nucleoside analogues with a 1,4-dioxane, 1,4-oxathiane or 1,4-oxazine ring structure have been prepared from the corresponding dimesylated seconucleosides by treatment with either sodium hydroxide, sodium sulfide or primary alkylamines.
The Chemistry of 2',3'-Seconucleosides. 1. Synthesis and Chemical and Biological Properties of Derivatives of 2',3'- Secouridine
Jones, A. Stanley,Walker, Richard T.,Wyatt, Paul G.,Balzarini, Jan,Clercq, Erik De
, p. 3520 - 3532 (2007/10/02)
Aspects of the chemistry of 2',3'-secouridine (1-(R)-1,5-dihydroxy-4-hydroxymethyl-3-oxapent-2-yl)uracil) derivatives have been studied. 5'-O-Trityl-2',3'-secouridine (4) was obtained from 5'-O-trityluridine by oxidation with periodate followed by reducti
