Crystal structure, Hirshfeld surface analysis, calculations of intermolecular interaction energies and energy frameworks and the DFT-optimized molecular structure of 1-[(1-butyl-1H-1,2,3-triazol-4-yl)methyl]-3-(prop-1-en-2-yl)-1H-benzimidazol-2-one

Article

作者: Cherkaoui, Hassan ; Zouhair, Mustapha ; Haoudi, Amal ; Hökelek, Tuncer ; El Atrassi, Zakaria ; Sebbar, Nada Kheira ; Blacque, Olivier ; Mazzah, Ahmed

The benzimidazole entity of the title molecule, C17H21N5O, is almost planar (r.m.s. deviation = 0.0262 Å). In the crystal, bifurcated C—H...O hydrogen bonds link individual molecules into layers extending parallel to the ac plane. Two weak C—H...π(ring) interactions may also be effective in the stabilization of the crystal structure. Hirshfeld surface analysis of the crystal structure reveals that the most important contributions for the crystal packing are from H...H (57.9%), H...C/C...H (18.1%) and H...O/O...H (14.9%) interactions. Hydrogen bonding and van der Waals interactions are the most dominant forces in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the stabilization of the title compound is dominated via dispersion energy contributions. The molecular structure optimized by density functional theory (DFT) at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined molecular structure in the solid state.

2024-05-01·Journal of Fluorescence

Synthesis of Fluorescent C–C Bonded Triazole-Purine Conjugates

Article

作者: Traskovskis, Kaspars ; Chu, Han-Wei ; Turks, Māris ; Chang, Huan-Tsung ; Novosjolova, Irina ; Juršėnas, Saulius ; Jovaišaitė, Justina ; Burcevs, Aleksejs ; Sebris, Armands

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.

2024-01-31·ACS Applied Materials & Interfaces

Exploring a Fused Triazole–Tetrazine Binary CN Material for a Promising Initiating Substance

Article

作者: Cai, Jinxiong ; Yin, Ping ; Pang, Siping ; Zhang, Hui ; Lai, Qi ; Li, Zhimin

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.

100 项与 BMS-585248 相关的药物交易

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