13345-72-7Relevant academic research and scientific papers
A convenient, high-yield synthesis of 1-substituted uracil and thymine derivatives
Rejman, Dominik,Kova?ková, Soňa,Pohl, Radek,Dra?ínsky, Martin,Fiedler, Pavel,Rosenberg, Ivan
experimental part, p. 8513 - 8523 (2010/01/06)
Novel reagents for the synthesis of 1-substituted uracil and thymine derivatives have been developed. The aminolysis of 2- or 4-nitrophenyl 3-ethoxyacryloylcarbamate and 3-ethoxy-2-methylacryloylcarbamate with a variety of primary amino derivatives procee
ANN-QSAR model for selection of anticancer leads from structurally heterogeneous series of compounds
Gonzalez-Diaz, Humberto,Bonet, Isis,Teran, Carmen,De Clercq, Erik,Bello, Rafael,Garcia, Maria M.,Santana, Lourdes,Uriarte, Eugenio
, p. 580 - 585 (2008/02/10)
Developing a model for predicting anticancer activity of any classes of organic compounds based on molecular structure is very important goal for medicinal chemist. Different molecular descriptors can be used to solve this problem. Stochastic molecular descriptors so-called the MARCH-INSIDE approach, shown to be very successful in drug design. Nevertheless, the structural diversity of compounds is so vast that we may need non-linear models such as artificial neural networks (ANN) instead of linear ones. SmartMLP-ANN analysis used to model the anticancer activity of organic compounds has shown high average accuracy of 93.79% (train performance) and predictability of 90.88% (validation performance) for the 8:3-MLP topology with different training and predicting series. This ANN model favourably compares with respect to a previous linear discriminant analysis (LDA) model [H. Gonzalez-Diaz et al., J. Mol. Model 9 (2003) 395] that showed only 80.49% of accuracy and 79.34% of predictability. The present SmartMLP approach employed shorter training times of only 10 h while previous models give accuracies of 70-89% only after 25-46 h of training. In order to illustrate the practical use of the model in bioorganic medicinal chemistry, we report the in silico prediction, and in vitro evaluation of six new synthetic tegafur analogues having IC50 values in a broad range between 37.1 and 138 μg mL-1 for leukemia (L1210/0) and human T-lymphocyte (Molt4/C8, CEM/0) cells. Theoretical predictions coincide very well with experimental results.
1-cyclopentyluracils: Synthesis and conformational analysis by X-ray crystallography and AM1 theoretical calculations
Teran,Teijeira,Santana,Uriarte,Castineiras
, p. 69 - 75 (2007/10/03)
A series of 1-cyclopentyl 5-substituted pyrimidines was synthesized and their energy-minimized structures were determined by AM1 and compared with the crystal structure of the parent compound, 1-cyclopentyluracil (2). As has been reported for other nucleoside analogues, the energy-minimized conformations were similar for all the compounds, but were not fully in agreement with the X-ray crystal structure obtained for 2.
Synthesis of meso-2',3'-Dideoxy-3'β-hydroxymethyl Carbocyclic Nucleosides as Potential Antiviral Drugs. Unusual Competitive 2-O-versus N1-Alkylation of 3-Substituted Pyrimidines under Mitsunobu Conditions
Bonnal, Christophe,Chavis, Claude,Lucas, Marc
, p. 1401 - 1410 (2007/10/02)
The synthesis of meso-2',3'-dideoxy-3'β-hydroxymethyl carbocyclic nucleosides as potential antiviral drugs via the alkylation of protected purines and pyrimidines with meso-β,β'-disubstituted cyclopentanols under Mitsunobu conditions is described.Chemical
