Burcevs Aleksejs, Jonusauskas Gediminas, Novosjolova Irina, Turks Māris
Institute of Chemistry and Chemical Technology, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, Latvia.
Laboratoire Ondes et Matière d'Aquitaine, Bordeaux University, UMR CNRS 5798, 351 Cours de la Libération, 33405 Talence, France.
Molecules. 2025 Apr 4;30(7):1612. doi: 10.3390/molecules30071612.
Purine-1,4,7,10-tetraazacyclododecane (cyclen) conjugate was designed to study its Cu ions complexation capability. Several synthetic approaches were tested to achieve the target compound. The optimal approach involved stepwise modifications of purine 9, 8, and 6 positions that, in nine consecutive steps, provided purine-cyclen conjugate. The synthetic sequence involved Mitsunobu-type alkylation at 9 and iodination at 8, followed by Stille, SAr, CuAAC, and alkylation reactions. The designed purine-cyclen conjugate is able to complex Cu ions in both the cyclen part and between the purine 7 and triazole 2 positions. The complexation pattern and equilibrium were studied using the NMR titration technique in MeCN-d and absorption spectra.
设计嘌呤 - 1,4,7,10 - 四氮杂环十二烷（环烯）共轭物以研究其与铜离子的络合能力。测试了几种合成方法以获得目标化合物。最佳方法涉及对嘌呤的9、8和6位进行逐步修饰，通过九个连续步骤得到嘌呤 - 环烯共轭物。合成序列包括9位的光延型烷基化和8位的碘化，随后进行施蒂勒反应、亲核芳基取代反应、铜催化的叠氮化物 - 炔烃环加成反应和烷基化反应。所设计的嘌呤 - 环烯共轭物能够在环烯部分以及嘌呤7位和三唑2位之间与铜离子络合。使用氘代乙腈中的核磁共振滴定技术和吸收光谱研究了络合模式和平衡。
