- METHOD FOR SYNTHESIZING DIVERSELY SUBSTITUTED PURINES
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The present invention relates to a method for synthesizing diversely substituted purines starting from a pyrimidine. Formula (I). The method comprises the formation of an amidine group on the pyrimidine by implementing a Vilsmeier type reagent, the functi
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Page/Page column 21; 37
(2018/12/03)
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- A One-Pot Synthesis of Highly Functionalized Purines
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Highly substituted purines were synthesized in good to high yields through a one-pot straightforward metal-free scalable method, using the Traube synthesis adapted to Vilsmeier-type reagents. From 5-amino-4-chloropyrimidines, new 9-aryl-substituted chloropurines and intermediates for peptide nucleic acid synthesis were prepared. Variant procedures allowing a rapid synthesis of ribonucleosides and 7-benzylpurine from 5-amidino-6-aminopyrimidines are also reported to illustrate the high potential of this versatile toolbox. This route appears to be particularly interesting in the field of nucleic acids for a direct and rapid access to various new 8-alkylpurine nucleosides.
- Zelli, Renaud,Zeinyeh, Wa?l,Haudecoeur, Romain,Alliot, Julien,Boucherle, Benjamin,Callebaut, Isabelle,Décout, Jean-Luc
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supporting information
p. 6360 - 6363
(2017/12/08)
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- Enhanced selectivity for inhibition of analog-sensitive protein kinases through scaffold optimization
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The ability to inhibit any protein kinase of interest with a small molecule is enabled by a combination of genetics and chemistry. Genetics is used to modify the active site of a single kinase to render it distinct from all naturally occurring kinases. Next, organic synthesis is used to develop a small molecule, which does not bind to wild-type kinases but is a potent inhibitor of the engineered kinase. This approach, termed chemical genetics, has been used to generate highly potent mutant kinase-specific inhibitors based on a pyrazolopyrimidine scaffold. Here, we asked if the selectivity of the resulting pyrazolopyrimidines could be improved, as they inhibit several wild-type kinases with low-micromolar IC50 values. Our approach to improve the selectivity of allele-specific inhibitors was to explore a second kinase inhibitor scaffold. A series of 6,9-disubstituted purines was designed, synthesized, and evaluated for inhibitory activity against several kinases in vitro and in vivo. Several purines proved to be potent inhibitors against the analog-sensitive kinases and exhibited greater selectivity than the existing pyrazolopyrimidines.
- Zhang, Chao,Shokat, Kevan M.
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p. 5832 - 5838
(2008/02/03)
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- Regioselective N-9 arylation of purines employing arylboronic acids in the presence of Cu(II)
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9-Arylpurines are efficiently formed with complete regioselectivity when purines are treated with arylboronic acids in the presence of copper(II) acetate. A variety of substituents on both coupling partners are well tolerated.
- Bakkestuen, Anne Kristin,Gundersen, Lise-Lotte
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p. 3359 - 3362
(2007/10/03)
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- ETHYL CHLOROFORMATE/DMF IN ORGANIC SYNTHESIS. I. A NOVEL REAGENT FOR RING CLOSURE OF 5-AMINO-1-ARYL-4-IMIDAZOLECARBOXAMIDES TO THEIR HYPOXANTHINE DERIVATIVES
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Ethyl chloroformate/dimethylformamide mixture is used as a new reagent for adding a carbon (C-2 in the purine nucleus) at the formic acid oxidation level during ring closure of 5-amino-1-aryl-4-imidazolecarboxamides leading to the formation of the corresp
- El-Bayouki, Khairy A. M.,El-Sayed, Ali S.,Basyouni, Whaid M.
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p. 163 - 166
(2007/10/02)
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