Microwave-Assisted Synthesis and Properties of Novel Hexaazatrinaphthylene Dendritic Scaffolds.

A novel family of water-soluble π-conjugated hexaazatrinaphthylenes-based dendritic architectures constructed by hexaketocyclohexane and 1,2,4,5-benzenetetramine units is developed in a microwave-assisted organic synthesis (MAOS) approach. The structures and purity of these compounds are verified by 1H and 13C-NMR, MALDI-TOF MS, UV-vis, elemental analysis, DSC, AFM, STM and cyclic voltammetry.

In vitro activities of hexaazatrinaphthylenes against Leishmania spp.

The in vitro activity of a novel group of compounds, hexaazatrinaphthylene derivatives, against two species of Leishmania is described in this study. These compounds showed a significant dose-dependent inhibition effect on the proliferation of the parasites, with 50% inhibitory concentrations (IC(50)s) ranging from 1.23 to 25.05 µM against the promastigote stage and 0.5 to 0.7 µM against intracellular amastigotes. Also, a cytotoxicity assay was carried out to in order to evaluate the possible toxic effects of these compounds. Moreover, different assays were performed to determine the type of cell death induced after incubation with these compounds. The obtained results highlight the potential use of hexaazatrinaphthylene derivatives against Leishmania species, and further studies should be undertaken to establish them as novel leishmanicidal therapeutic agents.

Novel organogelators based on amine-derived hexaazatrinaphthylene.

Novel C(3)-symmetrical heteroaromatic hexaazatrinaphthylene (HATNA) gelators symmetrically end-substituted with pendant aromatic and aliphatic amines were synthesized. Some of these π-conjugated structures induce self-assembly, forming fibers able to gelate solvents of different polarity at low wt% as demonstrated by spectroscopic and microscopic techniques.

Instantaneous low temperature gelation by a multicomponent organogelator liquid system based on ammonium salts.

A new synergistic multicomponent organogelator liquid system (MOGLS) was discovered during the standard protocol of tartaric acid-mediated racemic resolution of (+/-)- trans-1,2-diaminocyclohexane. The MOGLS is formed by a 0.126 M methanolic solution of (1 R,2 R)-(+)-1,2-diaminocyclohexane L-tartrate and 1 equiv of concentrated hydrochloric acid. Nonreversible gelation of oxygenated and nitrogenated solvents occurs efficiently at low temperature. Several features make this system unique: (1) it is a multicomponent solution where each of the five components is required for the organogelation property; (2) the multicomponent organogelator liquid system (MOGLS) is formed by simple, small, and commercially available chiral building blocks dissolved in a well-defined solvent system (MeOH/HCl/H2O); (3) the chiral building blocks are easily amenable for further modifications in structure-property relationship studies; (4) the gelation phenomenon takes place efficiently at low temperature upon warming up the isotropic solution, conversely to the typical gel preparation protocol (gel formation upon cooling down the isotropic solution); (5) the formed organic gels are not thermoreversible in spite of the noncovalent interactions that hold the 3D-fibrillar network together.