700-00-5Relevant articles and documents
A versatile methodology for the regioselective C8-metalation of purine bases
Brackemeyer, Dirk,Hervé, Alexandre,Schulte To Brinke, Christian,Jahnke, Mareike C.,Hahn, F. Ekkehardt
supporting information, p. 7841 - 7844 (2014/06/23)
Purine nucleobases are excellent ligands for metal ions, forming normally coordinative Werner-type bonds by utilizing the N donor atoms of the nucleobase skeleton. Here we show that purines such as 8-chlorocaffeine and 8-bromo-9-methyladenine react with [Pt(PPh3)4] under oxidative addition of the C8-halogen bond to the metal center. The resulting PtII complexes feature a C8-bound ylidene ligand. Protonation of the ylidene at the N7/9-atom yields complexes bearing a protic N-heterocyclic carbene ligand derived from the purine base with an NMe,NH-substitution pattern.
8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands
Lambertucci, Catia,Antonini, Ippolito,Buccioni, Michela,Dal Ben, Diego,Kachare, Dhuldeo D.,Volpini, Rosaria,Klotz, Karl-Norbert,Cristalli, Gloria
experimental part, p. 2812 - 2822 (2009/09/08)
Importance of making available selective adenosine receptor antagonists is boosted by recent findings of adenosine involvement in many CNS dysfunctions. In the present work a series of 8-bromo-9-alkyl adenines are prepared and fully characterized in radio
Alkylation of Adenine with Functionalized tert.-Propargyl Carbonates. Synthesis of 3'-Hydroxymethyladenallene - a New Analogue of 2'-Deoxyadenosine
Xu, Ze-Qi,Joshi, Ramachandra V.,Zemlicka, Jiri
, p. 67 - 76 (2007/10/02)
Esters 9d - 9g derived from acetylenic carbinol 5 were prepared and they were studied as potential alkylating agents with adenine (10), N6-benzoyl- and N6-dimethylamino-methyleneadenine (16 and 17).Carbonates 9f and 9g were the most suitable giving allene 11 and acetylene 12 (after N-deprotection in case of 16 and 17).On a scale larger than 0.2 mmol, slow addition of carbonate 9f or 9g to a solution of 10, 16 or 17 in DMF at 60 degC was most conducive to formation of allenic derivative 11.Such conditions also supperessed formation of by-products such as carbonate 13a and N9-methyladenine (14) observed in the case of methyl carbonate 9f.Intermediates 11 and 12 were deprotected using BCl3 in CH2Cl2 to give 3'-hydroxymethyladenallene (4a) and diol 15, respectively.Compound 4a was deaminated with adenosine deaminase.
