4121-39-5Relevant academic research and scientific papers
Customizable and Regioselective One-Pot N?H Functionalization of DNA Nucleobases to Create a Library of Nucleobase Derivatives for Biomedical Applications
Borges, Jo?o,Machado, Carmen M.,Mano, Jo?o F.,Rocha, Djenisa H. A.,Silva, Artur M. S.,Silva, Vera L. M.,Sousa, Cristiana F. V.,Sousa, Vera
, p. 4423 - 4433 (2021/08/30)
DNA is one of the most exciting biomolecules in nature for developing supramolecular biofunctional nanoarchitectures owing to the highly specific and selective interactions between complementary Watson-Crick base pairing. Herein, simple and one-pot synthetic procedures have been implemented for producing a library of DNA nucleobase derivatives endowed with reactive functional groups for bioconjugation and cross-linking strategies with other (bio)molecules. Purine and pyrimidine molecules have been regioselectively N?H functionalized either via N-alkylation, N-allylation, N-propargylation or Michael-type reactions and structurally characterized. The influence of the reaction conditions was assessed and discussed. The in vitro biocompatibility of the native and nucleobase derivatives was evaluated by culturing them with human fibroblasts, revealing their cytocompatibility. The library of nucleobase derivatives holds great promise for being coupled to different biomolecules, including biopolymeric materials, lipids, and peptides, thus potentially leading to modular supramolecular nanobiomaterials for biomedicine.
Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir
Qin, Tao,Li, Jian-Ping,Xie, Ming-Sheng,Qu, Gui-Rong,Guo, Hai-Ming
, p. 15512 - 15523 (2019/01/04)
An efficient method to construct chiral acyclic nucleosides via Sharpless asymmetric dihydroxylation of N-allylpyrimidines or N-alkenylpurines is reported. A range of chiral acyclic nucleosides with two adjacent hydroxyl groups present on the side chains could be produced in good yields (up to 97% yield) and excellent enantioselectivities (90-99% ee). The synthetic utility of the reaction was demonstrated by the catalytic asymmetric synthesis of (S)-Cidofovir and (R)-Buciclovir.
The Convenient Synthesis of Unsaturated Nucleoside Analogues in Water under Microwave Irradiation
Xia, Ran,Sun, Li-Ping
, p. 76 - 82 (2016/03/01)
A convenient method for the regioselective synthesis of unsaturated nucleoside analogs in water under microwave irradiation was developed. All pyrimidine and purine nucleoside derivatives were exclusively alkylated at N1 and N9 respectively in good to excellent yields. In addition, this system could tolerate a broad range of functional groups, such as chloro, bromo, iodo, alkyl, amino, and hydroxyl groups. More importantly, the reaction scale could be enlarged to 50 mmol which made this route attractive for industrial application.
Design, synthesis, antiviral, and cytostatic evaluation of novel isoxazolidine analogs of homonucleotides
Lysakowska, Magdalena,Balzarini, Jan,Piotrowska, Dorota G.
, p. 341 - 353 (2014/05/20)
Moderate diastereoselectivities (d.e. 2-62%) of isoxazolidine homonucleotides were observed for cycloadditions between N-methyl-C- (diethoxyphosphoryl)nitrone and N-allyl nucleobases, with trans-isoxazolidines predominating. The stereochemistry of the substituted isoxazolidines was established based on 2D NOE experiments performed for uracil-containing cycloadducts. The cis- and trans-isoxazolidine phosphonates obtained herein were evaluated in vitro for activity against a broad range of DNA and RNA viruses. None of the compounds were endowed with antiviral activity at subtoxic concentrations, but some of them were found to inhibit the proliferation of L1210 cells with IC50 values in the range of 33-100 μM.
A new 9-alkyladenine-cyclic methylglyoxal diadduct activates wt- and F508del-cystic fibrosis transmembrane conductance regulator (CFTR) in vitro and in vivo
Boucherle, Benjamin,Bertrand, Johanna,Maurin, Bruno,Renard, Brice-Lo?c,Fortuné, Antoine,Tremblier, Brice,Becq, Frédéric,Norez, Caroline,Décout, Jean-Luc
, p. 455 - 465 (2014/07/21)
Cystic fibrosis transmembrane conductance regulator (CFTR) is the main chloride channel present in the apical membrane of epithelial cells and the F508 deletion (F508del-CFTR) in the CF gene is the most common cystic fibrosis-causing mutation. In the sear
Synthesis of N-alkenylpurines by rearrangements of the corresponding N-allyl isomers: Scopes and limitations
Kania, Jindrich,Gundersen, Lise-Lotte
, p. 2008 - 2019 (2013/05/08)
N-9- and N-7-alkenylpurines have been synthesized by rearrangement of the corresponding N-allyl derivatives, often in good yields and with high stereoselectivity. Base promoted and transition metal mediated rearrangements have been studied. Simple allylpurines were easily rearranged with catalytic amounts of RuClH(CO)(PPh3)3. The efficiency of base promoted rearrangement was highly dependent on the detailed structure of the starting material, but this reaction often occurred with surprisingly high Z-selectivity. N-Alkenylpurines have been synthesized, often in good yields, from the corresponding more readily available N-allyl isomers by a double bond migration. The scope and limitation of the rearrangement in the presence of various bases or transition metal complexes have been studied.
Synthesis of modified homo-N-nucleosides from the reactions of mesityl nitrile oxide with 9-allylpurines and their influence on lipid peroxidation and thrombin inhibition
Thalassitis, Andreas,Hadjipavlou-Litina, Dimitra J.,Litinas, Konstantinos E.,Miltiadou, Panagiotis
experimental part, p. 6433 - 6436 (2010/06/11)
9-(3-Mesityl-4,5-dihydroisoxazol-5-yl) homo-N-nucleosides were prepared from the 1,3-dipolar cycloaddition reactions of mesityl nitrile oxide with 9-allyl derivatives of 6-chloropurine, 6-piperidinylpurine, 6-morpholinylpurine, 6-pyrrolidinylpurine, and 6
Synthesis of silicon analogues of acyclonucleotides incorporable in oligonucleotide solid-phase synthesis
Thibon, Jacques,Latxague, Laurent,Deleris, Gerard
, p. 4635 - 4642 (2007/10/03)
The synthesis of the four silicon analogues of acyclonucleosides was described. In every case, the silicon atom was introduced onto an allyl group on the natural nucleobase following a hydrosilylation reaction. Diols obtained were protected as 4,4'-dimethoxytrityl ethers and subsequently activated as 2-cyanoethyl N,N-diisopropylchlorophosphoramidite in order to be suitable for oligonucleotide solid phase synthesis.
Regiochemistry and Stereochemistry in Pd(0)-Catalyzed Allylic Alkylation of Nucleoside Bases
Gundersen, Lise-Lotte,Benneche, Tore,Rise, Frode,Gogoll, Adolf,Undheim, Kjell
, p. 761 - 771 (2007/10/02)
Allylic alkylation of amino- and hydroxy-azaheterocycles, in particular nucleoside bases, has been effected using Pd(0)-catalysis.A method has been developed for the preparation of carbocyclic nucleoside analogs such as the antiviral agent Carbovir.The synthesis of an appropriately substituted cyclopentenyl acetate for this reaction is described.Carbocyclic nucleosides of thymine at N-1, of adenine at N-9 and guanine at N-9 are described.Regiochemistry and stereochemistry of the products and intermediates have been determined by NMR studies.The (trimethylsilyl)ethyl group has been found to be an excellent protecting group for the 6-OH group in guanine, and it is readily removed by fluoride ions.
