BMS-585248

A design toward C-C bonded 2,6-bis(1H-1,2,3-triazol-4-yl)-9H-purine and 2-piperidinyl-6-(1H-1,2,3-triazol-4-yl)-9H-purine derivatives was established using the combination of Mitsunobu, Sonogashira, copper (I) catalyzed azide-alkyne cycloaddition, and S_NAr reactions. 11 examples of 2,6-bistriazolylpurine and 14 examples of 2-piperidinyl-6-triazolylpurine intermediates were obtained, in 38-86% and 41-89% yields, respectively. Obtained triazole-purine conjugates expressed good fluorescent properties which were studied in the solution and in the thin layer film for the first time. Quantum yields reached up to 49% in DMSO for bistriazolylpurines and up to 81% in DCM and up to 95% in DMSO for monotriazolylpurines. Performed biological studies in mouse embryo fibroblast, human keratinocyte, and transgenic adenocarcinoma of the mouse prostate cell lines showed that most of obtained triazole-purine conjugates are not cytotoxic. The 50% cytotoxic concentration of the tested derivatives was in the range from 59.6 to 1528.7 µM.

The pursuit of binary carbon-nitrogen (CN) materials with high density and good thermal stability presents a significant challenge due to the inherent trade-off between high-energy storage and low bond dissociation energy. In this study, we designed and synthesized (S)-1,2-bis(3-azido-1H-1,2,4-triazol-1-yl)diazene (BAzTD) and 2,9-diazidobis([1,2,4]-triazolo)[1,5-d:5',1'-f][1,2,3,4]tetrazine (DAzTT) through a straightforward reaction. Remarkably, DAzTT demonstrated a high density of 1.816 g·cm^-3 (at 298 K) and a considerable thermal decomposition temperature of 216.86 °C. These properties outperform those of previously reported binary heterocyclic CN compounds and polyazido heterocyclic compounds. The quantum-chemical methods further substantiated the integral role of aromaticity as the driving force behind this difference. Additionally, the initiation capability of DAzTT was evaluated by a notably low minimum primary charge (MPC = 40 mg), surpassing conventional organic primary explosives, such as commercial 2-diazo-4,6-dinitrophenol (DDNP, MPC = 70 mg). The exceptional priming ability highlights the potential as an environmentally friendly replacement for toxic lead azide. DAzTT sets a new standard for binary CN compounds and provides a valuable precursor for high-nitrogen carbon nitride materials.