Anthranilamide

We have studied several protecting groups for vinylboronic-acid derivatives as monomers in radical polymerizations with the objective to improve the polymerization ability and C-B bond-cleaving post-transformation performance. Anthranilamide (aam)-protected vinylboronic acid (VBaam) exhibited experimentally a relatively high polymerization activity, which was theoretically corroborated by density functional theory (DFT) calculations that revealed a peculiar effect of the interaction between the aam groups on the polymerization behavior. The VBaam units in the copolymers can subsequently be transformed into vinyl alcohols or into ethylene units through C-B-bond-cleaving side-chain replacement, which affords valuable copolymers such as poly(vinyl alcohol-co-styrene), poly(ethylene-co-styrene), and poly(ethylene-co-acrylate).

A gallium-containing MCM-22 (Mobil Composition of Matter No. 22) zeolite material was prepared using a simple hydrothermal method. Fourier transform infrared spectroscopy analysis and powder X-ray diffraction provide evidence of the formation of a pure MCM-22 phase framework and an MWW (MCM-tWenty-tWo) structure. Scanning electron microscopy images showed a uniform spherical shape, interpenetrating the platelet structure and a uniform particle size of approximately 6 μm. 71Ga nuclear magnetic resonance studies confirmed the presence of gallium in both the tetrahedral framework and the octahedral extra-framework environment. From the sorption studies, the presence of strong acidic sites and the microporous nature of the material were evident. The resultant Ga-MCM-22 material showed an excellent isolated yield of 95% in the synthesis of 2,3-dihydroquinazolin-4(1H)-ones by cyclocondensation of anthranilamide with aldehydes in ethanol. The scope of the reaction was further explored by employing various cyclic, aromatic, and aliphatic aldehydes with anthranilamide. The results provide a very good yield (85-95%). A significant advantage of the developed protocol includes high yield, use of a green solvent, and easy removal of the catalyst through filtration within a short reaction time.

In this study, we prepared antibacterial hydrogels through the self-assembly of naphthyl anthranilamide (NaA) capped amino acid based cationic peptide mimics. These ultra-short cationic peptide mimics were rationally designed with NaA as a capping group, L-phenylalanine, a short aliphatic linker, and a cationic group. The synthesized peptide mimics efficiently formed hydrogels with minimum gel concentrations between 0.1 and 0.3%w/v. The resulting hydrogels exhibited desirable viscoelastic properties which can be tuned by varying the cationic group, electronegative substituent, or counter anion. Importantly, nanofibers from the NaA-capped cationic hydrogels were found to be the source of hydrogels' potent bacteriacidal actvity against both Gram-positive and Gram-negative bacteria while remaining non-cytotoxic. These intrinsically antibacterial hydrogels are ideal candidates for further development in applications where bacterial contamination is problematic.