10.1039/b915533c
The research proposes O-silylated C3-halohydrins as novel protected building blocks for the total, regio-, and stereocontrolled synthesis of glycerolipid frameworks. The purpose is to develop efficient methods for synthesizing various glycerolipids with specific structures, which are important for biochemical and pharmacological studies. Key chemicals include O-silylated C3-halohydrins such as 1(3)-O-silyl-2-O-acyl-, 1,2(2,3)-O-bis(silyl)-, and 1(3)-O-acyl-2-O-silyl-3(1)-halo-sn-glycerides. These compounds allow for the displacement of iodine by carboxylates, selective acylation, direct exchange of O-silyl protection for trichloroacetyl groups, and conversion of TBDMS groups into trifluoroacetates without affecting other functional groups. The methodology is entirely regio- and stereospecific, avoiding acyl migration and providing target compounds with chosen absolute configurations from a single synthetic precursor. The research concludes that this new strategy is high yielding, minimizes synthetic operations, and can be easily scaled up, offering a powerful method for the preparation of di- and triacylglycerols as well as glycerol-based cationic lipids.
10.1016/j.bmc.2010.11.001
The research focuses on the synthesis and antibacterial activity study of a novel class of cationic anthraquinone analogs. The purpose of the study was to investigate the effect of leaving groups and additives on the selectivity between the formation of 1-alkyl-1H- and 2-alkyl-2H-naphtho[2,3-d]triazole-4,9-diones, which are analogs of anthraquinone or naphthoquinone fused with 1,2,3-triazole. The researchers developed a novel class of antibacterial cationic anthraquinone analogs that exhibit different antibacterial profiles. Notably, one lead compound, 4e, showed high potency and selectivity against Gram-positive pathogens, including methicillin-resistant Staphylococcus aureus (MRSA), while showing modest activity against Gram-negative bacteria. Other lead compounds, 4f and 4g, exhibited broad antibacterial activity against both MRSA and vancomycin-resistant Enterococcus faecalis (VRE). The chemicals used in the process included naphthoquinone, sodium azide, alkyl halides, and various leaving groups such as bromide, chloride, tosylate, mesylate, and trifluoroacetate. The synthesis involved a one-pot cycloaddition process and subsequent methylation to improve solubility and bioavailability, leading to the development of cationic compounds with significant antibacterial activity. The conclusions of the study suggest that these cationic compounds could pave the way for the development of new therapeutic agents, especially due to their unique antibacterial profiles and potential to avoid complications like Clostridium difficile infection (CDI).