158227-80-6Relevant articles and documents
Preparation process of ridecevir mother nucleus intermediate
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Paragraph 0025-0027; 0029, (2021/10/27)
The invention discloses a preparation process of a ridecevir mother nucleus intermediate (3aR,4R,6S,6aS)-6-(4-aminopyrrole[2,1-f][1,2,4]triazine-7-yl)-2,2-dimethyltetrahydrofuran[3,4-d][1,3]dioxo-4-yl)methanol. The preparation method comprises the following steps: carrying out a coupling reaction on a pyrrole triazine halide II serving as a raw material and a halide III under the promotion of a metal reagent MX to obtain a coupling product IV with high stereoselectivity; and carrying out a free radical reaction on the IV and a cyaniding reagent in the presence of an oxidizing agent, and carrying out a boron trichloride debenzylation reaction on the obtained intermediate to obtain the ridecevir mother nucleus intermediate I with high stereoselectivity. The method has the main beneficial effects that the process route is relatively short, the reaction condition is mild, tedious procedures such as strong acidity and column chromatography separation and purification are avoided from the source, the reaction yield is high, the stereoselectivity is good, the method is easy to industrialize, and the method has relatively high implementation value and social and economic benefits.
Synthesis and evaluation of a collection of purine-like C-nucleosides as antikinetoplastid agents
Bouton, Jakob,Maes, Louis,Karalic, Izet,Caljon, Guy,Van Calenbergh, Serge
, (2021/01/06)
The kinetoplastid parasites Trypanosoma brucei, Trypanosoma cruzi and Leishmania spp. are the causative agents of neglected tropical diseases with a serious burden in several parts of the world. These parasites are incapable of synthesizing purines de nov
N-t-butyloxycarboryl protected heterocyclic compound and preparation method thereof and method for preparing C-nucleoside analogue by N-t-butyloxycarboryl protected heterocyclic compound
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, (2019/05/28)
The invention belongs to the field of chemical synthesis and particularly discloses an N-t-butyloxycarboryl protected heterocyclic compound shown in a general formula 5 as shown in the specification,a preparation method of the N-t-butyloxycarboryl protected heterocyclic compound and a method for preparing C-nucleoside analogue by the N-t-butyloxycarboryl protected heterocyclic compound. In the compound 5, Hal is selected from chlorine, bromine and iodine; Z is selected from CR0 or nitrogen; R0 refers to H, halogen, a cyano group, C1-C6 straight chain or branched alkyl, C2-C6 straight chain orbranched alkenyl or C2-C6 straight chain or branched alkynyl. In existing documents, synthesized C-nucleosides are mainly beta-C-nucleosides, but stereoselectivity of beta: alpha is unsatisfactory, and expensive synthesis raw materials are consumed while problems of product separation and purification exist. According to the method, an alpha-C-nucleoside product 8 or a beta-C-nucleoside product 3is controllably synthesized by starting from the easy-to-prepare low-cost compound 5, and high stereoselectivity, high yield, high repeatability and remarkable advantages are realized.
Synthesis and Biological Evaluation of Pyrrolo[2,1-f][1,2,4]triazine C-Nucleosides with a Ribose, 2′-Deoxyribose, and 2′,3′-Dideoxyribose Sugar Moiety
Li, Qingfeng,Lescrinier, Eveline,Groaz, Elisabetta,Persoons, Leentje,Daelemans, Dirk,Herdewijn, Piet,De Jonghe, Steven
, p. 97 - 104 (2018/01/12)
The synthesis of hitherto unknown pyrrolo[2,1-f][1,2,4]triazine C-nucleosides is described. Structural variations (chlorine, bromine, iodine, and cyano groups) were introduced at position 7 of 4-aza-7,9-dideazaadenine. In addition, pyrrolo[2,1-f][1,2,4]triazine C-nucleosides bearing a 2′-deoxy-, 2′,3′-dideoxy-, and 2′,3′-dehydrodideoxyribose moiety were also prepared. Among these analogues, the pyrrolo[2,1-f][1,2,4]triazine C-ribonucleosides with either a hydrogen atom or cyano group at position 7 of the nucleobase displayed potent cytotoxic activity in a panel of various cancer cell lines.
SUBSTITUTED NUCLEOSIDE ANALOGUES FOR USE AS PRMT5 INHIBITORS
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, (2017/09/27)
The present invention relates novel substituted nucleoside analogues of Formula (I) wherein the variables have the meaning defined in the claims. The compounds according to the present invention are useful as PRMT5 inhibitors. The invention further relates to pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.
4'-SUBSTITUTED NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS
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, (2015/12/08)
Provided is 4'-substituted nucleoside derivatives of Formula I and their use in the inhibition of HIV reverse transcriptase, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis, treatment, and delay in the onset or progression of AIDS and/or ARC.
PYRROLO[1,2-f][1,2,4]TRIAZINES USEFUL FOR TREATING RESPIRATORY SYNCITIAL VIRUS INFECTIONS
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Paragraph 0184-0189, (2015/05/26)
Provided herein are formulations, methods and substituted tetrahydrofuranyl-pyrrolo[1,2-f][1,2,4]triazine-4-amine compounds of Formula (I) for treating Pneumovirinae virus infections, including respiratory syncytial virus infections, as well as methods and intermediates for synthesis of tetrahydrofuranyl-pyrrolo[1,2-f][1,2,4]triazine-4-amine compounds.
Practical synthesis of 1′-substituted Tubercidin C-nucleoside analogs
Metobo, Sammy E.,Xu, Jie,Saunders, Oliver L.,Butler, Thomas,Aktoudianakis, Evangelos,Cho, Aesop,Kim, Choung U.
, p. 484 - 486 (2012/02/02)
Several 1′-substituted analogs of Tubercidin C-nucleosides were prepared using a highly convergent synthesis. Good to high diastereoselectivity was achieved using a variety of nucleophiles targeting the 1′-position. The source for this stereoselectivity i
4-Aza-7,9-dideazaadenosine, a new cytotoxic synthetic C-nucleoside analogue of adenosine
Patil, Shirish A.,Otter, Brian A.,Klein, Robert S.
, p. 5339 - 5342 (2007/10/02)
The first synthesis of 10, the pyrrolo[2,1-f][1,2,4]triazine C-nucleoside congener of adenosine is described. The key intermediate ribofuranosyl pyrrole 4 is obtained by the direct C-ribosylation of pyrrolemagnesiumbromide with 2,3,5-tri-O-benzyl ribose followed by an acid-catalyzed dehydration. Vilsmeier formylation of 4 followed by N-amination and CHO -> CN conversion affords N-amino nitrile intermediate 7 which can be cyclized with formamidine acetate to the blocked title compound 9. Hydrogenolytic debenzylation completes the synthesis. In vitro growth inhibitory activities of 10 against leukemic cell lines (0.8 - 15 nM) are comparable to those of 9- deazaadenosine.