10.1016/j.bmc.2008.08.060
The research centers on the synthesis and assessment of sulfonamide analogs of KRN7000, which are known for activating natural killer (NK) T cells. The goal was to create compounds that could selectively stimulate the production of Th2-biased cytokines to potentially alleviate autoimmune diseases and enhance transplantation tolerance. The study involved synthesizing a range of sulfonamide analogs, including both aromatic and aliphatic types, using phytosphingosine as the starting material and employing various chemical reactions such as protection and deprotection of hydroxyl groups, glycosidation, and sulfonamide formation. The synthesized analogs were then tested for their bioactivity using mouse spleen cells in vitro to evaluate the production of Th1 and Th2 cytokines. The analysis was performed using a cytometric bead array (CBA) to quantify IFN-?, IL-4, and IL-13 levels, allowing the researchers to assess the cytokine profile induced by each analog. The findings indicated that most of the analogs were effective in promoting Th2-biased cytokine production, with certain analogs showing particularly high IL-4/IFN-? ratios, suggesting their potential in modulating immune responses towards a Th2 phenotype.
10.1021/jo00907a012
The research investigates the scope and limitations of the dimethyl sulfoxide-trifluoroacetic anhydride (DMSO-TFAA) reagent for the preparation of iminosulfuranes. The study aims to explore the efficiency and applicability of this reagent with various nitrogen-containing compounds, including aryl amines, amides, sulfonamides, and urea. The key chemicals used in the research are DMSO and TFAA, which form an intermediate reagent that reacts with the nitrogen compounds to produce iminosulfuranes. The research concludes that the DMSO-TFAA reagent is highly effective, yielding iminosulfuranes in 40-90% yields, and is particularly reactive even with aromatic amines containing certain ortho substituents. The study also highlights the reagent's ability to form iminosulfuranes from previously uncharacterized compounds like sulfanilamide and sulfadiazine. However, it notes limitations with relatively basic amines and certain aromatic compounds. The findings suggest that the DMSO-TFAA reagent is a valuable tool for the preparation of iminosulfuranes, offering a more efficient and versatile alternative to other activated DMSO reagents.
10.1016/S0223-5234(97)81681-9
The study investigates the development of more specific carbonic anhydrase (CA) inhibitors, focusing on Schiff bases derived from aromatic sulfonamides. The researchers synthesized 21 new Schiff bases using sulfanilamide, homosulfanilamide, and p-aminoethyl-benzenesulfonamide as starting materials, reacting them with various substituted benzene- and heterocyclic aldehydes. These compounds were characterized and tested for their inhibitory effects on three CA isozymes: CA I, CA II, and CA IV. The results showed that several of these new Schiff bases exhibited a modest two-fold selectivity for the membrane-bound CA IV compared to the cytosolic human isozymes CA I and II. This selectivity is attributed to a decreased potency against hCA II relative to classical inhibitors. The study suggests that these compounds could potentially lead to the development of low molecular weight, isozyme-specific CA IV inhibitors, which may have improved therapeutic profiles and fewer side effects.
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