1,2,3-Triazoles as leaving groups in purine chemistry: a three-step synthesis of N6-substituted-2-triazolyl-adenine nucleosides and photophysical properties thereof

The Synthesis and X-ray Studies of 6-pyrrolidinyl-2-triazolyl Purine Arabinonucleoside

“…Recently, we have reported a novel approach to the synthesis of N 6 -substituted-2-(1,2,3-triazol-1-yl)adenine nucleosides [1]. Here we report a full account on the synthesis and X-ray analysis of one distinct member from this class of compounds:…”

“…We have found that product 10 has fluorescent properties. Initially its absorption and emission spectra were measured in DMSO [1]. However, it is more interesting to obtain the photophysical characteristics of this substance in water, which is the most common solvent for biological studies.…”

“…Search for new anticancer and antiviral agents, adenosine receptor agonists and antagonists prompted a renewed interest in purine chemistry, resulting in numerous synthetic methodologies. To the best of our knowledge, 2,6-bis-(1,2,3-triazol-1-yl)purines have been synthesized for the first time by us [1], and only their chemical reactivity remains to be determined.…”

2,6-Dichloro-9-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine

“…For the synthesis, see: Vorbrü ggen (1995); Robins & Uznań ski (1981); Nair & Richardson (1982); Francom et al (2002); Francom & Robins (2003); Gerster & Robins (1966). The conditions were improved by using our previous studies (Kovalovs et al, 2013;Novosjolova et al, 2013). For the biological activity of purine nucleosides, their anticancer and antiviral activity and use as agonists and antagonists of adenosine receptors, see: Lech-Maranda et al (2006); Robak et al (2009); Gumina et al (2003); Fredholm et al (2011); Elzein & Zablocki (2008).…”

2,6-Bis[4-(4-butylphenyl)-1H-1,2,3-triazol-1-yl]-9-dodecyl-9H-purine

“…In 2013, we developed a method for the synthesis of 2,6-bis(triazolyl)purine nucleosides, which contained ribose, arabinopyranose and arabinofuranose as sugar moieties [9]. We successfully showed that these 2,6-bis(triazolyl)purine nucleosides participate in aromatic nucleophilic reactions with different Nand S-nucleophiles and that the triazolyl ring in purine C6 positions acts as a good leaving group [9,10].…”