115983-78-3Relevant articles and documents
Heterocyclic analogs of nucleosides: Synthesis and biological evaluation of some 1-(3-thianyl)uracil and 9-(3-thianyl)adenine derivatives
Hultin,Szarek
, p. 208 - 213 (1994)
The 1-(3-thianyl)uracil (9) and 9-(3-thianyl)adenine (14) nucleoside analogs have been prepared from the key intermediate, (±)-(3β,5β)-3-amino-5-(hydroxymethyl)thinae (6). Analog 9 was converted into a mixture of diastereomeric sulfoxides (10) that afforded, by a Pummerer reaction, a mixture of (±)-1-{(2'β,3'β,5'β)-2'-acetoxy-5'-(acetoxymethyl)thian-3'-yl}2, 4(1H,3H)-pyrimidinedione (11a) and its 6'-β isomer (11b). The EI mass spectra of the nucleoside analogs are discussed. The uracil nucleoside analogs have been evaluated also for their anti-HIV and antitumor activities.
Synthesis and antiviral evaluation of cyclopentyl nucleoside phosphonates
Wang, Mengmeng,Srivastava, Puneet,Liu, Chao,Snoeck, Robert,Andrei, Graciela,De Jonghe, Steven,Herdewijn, Piet
, p. 616 - 625 (2018)
The synthesis of both 2?-hydroxy-3?-deoxy and 2?-deoxy-3?-hydroxy cyclopentyl nucleoside phosphonates with the natural nucleobases adenine, thymine, cytosine and guanine from a single precursor has been performed. The guanine containing analogues showed antiviral activity. Especially the 3?-deoxy congener 23 was active, displaying an EC50 of 5.35 μM against TK+ VZV strain and an EC50 of 8.83 μM against TK? VZV strain, besides lacking cytotoxicity. However, the application of phosphonodiamidate prodrug strategy did not lead to a boost in antiviral activity.
Synthesis of new 1′(N)-homocarbanucleosides based on 1-methylcyclopenta[c]pyrazole scaffold
Garcia, Marcos D.,Caamano, Olga,Fernandez, Franco,Abeijon, Paula,Blanco, Jose Manuel
, p. 73 - 80 (2006)
A series of 1′-homocarbanucleosides was prepared by coupling a purine or pyrimidine to, or constructing it on, a protected 1-methylcyclopenta[c] pyrazole pseudosugar synthesized from (±)-(exo,exo)-1-methyl-4,5,6,7- tetrahydro-4,7-methanoindazole-5,6-diol
A short and novel synthesis of carbocyclic nucleosides and 4′-epi-carbocyclic nucleosides from 2-cyclopenten-1-ones
Gosselin, Gilles,Griffe, Ludovic,Meillon, Jean-Christophe,Storer, Richard
, p. 906 - 914 (2006)
Carbocyclic nucleoside analogues remain interesting target molecules having the potential to combine biological activity with greater metabolic stability than their sugar counterparts. This paper describes a rapid and versatile synthetic approach to such
Derivatives with uracil-benzothiazole structure, preparation method of derivatives, and application of anti-HCV drugs
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Paragraph 0048-0050, (2019/12/02)
According to the invention, a new series of uracil-benzothiazole NS5B RdRp inhibitors are designed and synthesized; the compounds have the structure shown in a general formula (1), wherein the uracil-benzothiazole NS5B RdRp inhibitor provided by the inven
Synthesis, antiviral, cytotoxic and cytostatic evaluation of N1-(Phosphonoalkyl)uracil derivatives
Rygielska-Tokarska, Dorota,Andrei, Graciela,Schols, Dominique,Snoeck, Robert,G?owacka, Iwona E.
, p. 1081 - 1090 (2017/01/11)
A series of N1-(phosphonoalkyl)uracils was prepared in a two-step reaction sequence from x- aminoalkylphosphonates and (E)-3-ethoxyacryloyl isocyanate followed by the uracil ring closure. Under standard conditions (NCS; NBS; I2/CAN) all N1-(phosphonoalkyl)uracils were transformed into the respective 5-halogeno derivatives to be later benzoylated at N3. All compounds were evaluated in vitro for activity against a broad variety of DNA and RNA viruses. One compound was slightly active against human cytomegalovirus in HEL cell cultures (EC50 = 45 μM) while another showed weak activity against varicella-zoster virus (TK+ VZV strain OKA and TK- VZV strain 07-1) with EC50 = 43 and 53 μM, respectively. In addition, several compounds exhibited noticeable inhibitory effects on the proliferation of human cervical carcinoma cells (HeLa) at a concentration lower than 200 μM.