70184-00-8Relevant articles and documents
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.
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.
Microwave-assisted N-allylation of uracil and thymine pyrimidine bases
Sacarescu,Atudosie,Simionescu,Sacarescu,Harabagiu
experimental part, p. 602 - 606 (2012/01/13)
This work presents a new synthetic approach to N(1)-allylation of pyrimidine nucleobases with allyl bromide. The increased efficiency of the proposed method is based on two specific elements: (a) the nucleoside N-deprotonation is carried out in a homogeneous system by using sodium methylsulfinyl- methylide in DMSO; (b) the allylation reaction is microwave-assisted. This method ensures high yields (87-88%) of the monoallylated products and short reaction time (1.5 h as compared to tens of hours for classical methods), and provides protection against side reactions. NMR analysis of the crude reaction mixture indicated a ratio of 6-8 : 1 between N(1)-allyl derivatives and N(1),N(3)-diallyl derivatives.
