79892-45-8Relevant academic research and scientific papers
Design, synthesis and characterization of N9/N7-substituted 6-aminopurines as VEGF-R and EGF-R inhibitors
Peifer, Christian,Buehler, Stefanie,Hauser, Dominik,Kinkel, Katrin,Totzke, Frank,Schaechtele, Christoph,Laufer, Stefan
experimental part, p. 1788 - 1793 (2009/06/18)
In this study we report on the design, synthesis and biological characterization of novel N9 or N7 arylethanone-substituted 6-aminopurines and 6-methoxypurines, respectively, as EGF-R and VEGF-R inhibitors. The compounds were initial
Synthese de pyrimidines et purines adamantylees par alkylation regioselective directe, an catalyse par transfert de phase
Hedayatullah, Mir,Roger, Annie
, p. 1093 - 1096 (2007/10/02)
The use of 1-adamantyl bromomethyl ketone, under phase transfer catalysis conditions, permits the regioselective N1-alkylation of uracil and thymine, the N9-alkylation of adenine and 8-azaadenine and the N7-alkylation of t
Heterocyclic Ambident Nucleophiles. IV* The alkylation of Metal Salts of Adenine
Rasmussen, Malcolm,Hope, Janet M.
, p. 535 - 542 (2007/10/02)
The N3:N7:N9 alkylation patterns for reactions of the lithium, sodium, and potassium salts of adenine with various alkylating agents in dimethyl sulfoxide were determined by 1H n.m.r. spectroscopy.Only for the Li+ salt was any significant effect of ionic association noticed.Of the alkylating agents used, only chloromethyl pivalate gave a concentration dependent alkylation pattern.The latter effect was most pronounced with the heterogenous alkylation conditions of anhydrous Na2CO3/HCONMe2, adenine, and chloromethyl pivalate; here, increasingconcentrations changed the main reaction from N7- to N9-alkylation.Solvent effects on the alkylation patterns were also studied.Within the common dipolar aprotic solvent group, (Me2N)3PO, HCONMe2 and Me2SO, effects were small; in protic solvents, particularly formamide, enhanced N3-alkylation was observed.
Heterocyclic Ambident Nucleophiles. III* The Alkylation of Sodium Adenide
Rasmussen, Malcolm,Hope, Janet M.
, p. 525 - 534 (2007/10/02)
The alkylation of sodium adenide in HCONMe2 (30 deg) with various alkylating agents was analysed by 1H n.m.r. spectroscopy.Widely varying N3:N7:N9 alkylation patterns were observed, depending on the alkylating agent.These patterns are interpreted in terms of the electrostatic, thermodynamic and steric factors involved in the different SN2 transition states appropriate to each alkylating agent.Hydrogen bonding association between the 6-amino group and certain carbonyl containing alkylating agents is proposed to explain the enhancedN7-alkylation in some cases.Support for this latter proposal was obtain from a comparison of the adenine alkylation results with the corresponding alkylation patterns of 6-pivaloylamino- and 6-chloro-purine.
