26482-55-3Relevant academic research and scientific papers
Preparation of novel 2,3,8-trisubstituted pyrido[3,4-b]pyrazines and pyrido[2,3-b]pyrazines
Antoine, Maud,Czech, Michael,Gerlach, Matthias,Guenther, Eckhard,Schuster, Tilmann,Marchand, Pascal
experimental part, p. 794 - 806 (2011/04/16)
A four-step synthesis of 8-bromo-2,3-disubstituted pyrido[3,4-b]pyrazines and a six-step synthesis of 8-amino-2,3-disubstituted pyrido[3,4-b]pyrazines have been developed. A particularly valuable feature of this synthetic route is the possibility to build
SYNTHESIS AND BIOLOGICAL EFFECTS OF ACYCLIC ANALOGS OF DEAZAPURINE NUCLEOSIDES
Dvorakova, Hana,Holy, Antonin,Votruba, Ivan,Masojidkova, Milena
, p. 629 - 648 (2007/10/02)
Deaza analogs of three basic types of S-adenosyl-L-homocyteine hydrolase (SAHase) inhibitors, (S)-DHPA (I), eritadenine (II) and AHPA (III), were prepared.Alkylation of 3-deazaadenine (V), 3-deazapurine (VI), 1-deazaadenine (VII) and 4-amino-6-bromo-5-cyanopyrrrolopyrimidine (XXII) with (R)-2,2-dimethyl-4-tosyloxymethyl-1,3-dioxolane (XIIIb), followed by acid hydrolysis, afforded the corresponding (S)-2,3-dihydroxypropyl derivatives XVIIa-XIXa and XXV.Reaction of V and VII with 2,3-O-cyclohexylidene-D-erythronolactone (XXIX) and subsequent removal of the protecting groups in an acid medium gave eritadenine analogs XXVII and XXVIII.Compounds V and VII were alkylated with bromoacetaldehyde diethyl acetal to give N-(2,2-diethoxyethyl) derivatives XXXII and XXXIII from which the substituted acetaldehyde derivatives were liberated in situ and converted into compounds XXX and XXXI by cyanohydrine reaction followed by acid hydrolysis.The alkylations were performed in dimethylformamide with sodium or cesium salts of the bases.Biological activity was observed only with 3-deazaadenine derivatives XVIIa, XXVII and XXX which exhibit both enzyme inhibitory and antiviral activities.
Substituent Effects on the Isomer Ratios in the Rearrangement of Some 2- and 4-Nitraminopyridines
Deady, Leslie W.,Korytsky, Olga L.,Rowe, Jeffrey E.
, p. 2025 - 2034 (2007/10/02)
The preparation, and rearrangement in 92percent sulfuric acid, of 4-X-2-nitramino- (1), 2-X-4-nitramino- (2), and 6-X-2-nitramino-pyridines (3) is reported (X=H,Me,MeO,Br,Cl,CO2H).The product isomer ratios can be explained by differential electronic stabilization of the appropriate ? complexes for aromatic nitration and steric effects seem relatively unimportant.Deuteration had no effect on the product distribution
