6097-18-3

Upstream product

• 50690-11-4 2,5-dimethylphenacyl chloride 
• 333-20-0 potassium thioacyanate 
• 115144-84-8 2-(2,5-dimethyl-phenyl)-acrylic acid 
• 1147550-11-5 ammonium thiocyanate 
• 2142-73-6 1-(2,5-dimethylphenyl)-1-ethanone 
• 75840-13-0 2-bromo-1-(2,5-dimethylphenyl)ethan-1-one 
• 74331-70-7 2-ethynyl-1,4-dimethylbenzene 
• 163276-49-1 1-thiocyanatopyrrolidine-2,5-dione 

Downstream Products

• 103985-99-5 4-(2,5-dimethyl-phenyl)-3H-thiazol-2-one 

Relevant academic research and scientific papers

Structure-activity relationship studies in substituted sulfamoyl benzamidothiazoles that prolong NF-κB activation

In the face of emerging infectious diseases, there remains an unmet need for vaccine development where adjuvants that enhance immune responses to pathogenic antigens are highly desired. Using high-throughput screens with a cell-based nuclear factor κB (NF-κB) reporter assay, we identified a sulfamoyl benzamidothiazole bearing compound 1 that demonstrated a sustained activation of NF-κB after a primary stimulus with a Toll-like receptor (TLR)-4 agonist, lipopolysaccharide (LPS). Here, we explore systematic structure–activity relationship (SAR) studies on compound 1 that indicated the sites on the scaffold that tolerated modification and yielded more potent compounds compared to 1. The selected analogs enhanced release of immunostimulatory cytokines in the human monocytic cell line THP-1 cells and murine primary dendritic cells. In murine vaccination studies, select compounds were used as co-adjuvants in combination with the Food and Drug Administration approved TLR-4 agonistic adjuvant, monophosphoryl lipid A (MPLA) that showed significant enhancement in antigen-specific antibody titers compared to MPLA alone. Additionally, our SAR studies led to identification of a photoaffinity probe which will aid the target identification and mechanism of action studies in the future.

Visible-Light-Mediated Additive-Free Decarboxylative Ketonization Reaction of Acrylic Acids: An Access to α-Thiocyanate Ketones

Visible-light-mediated additive-free decarboxylative functionalization of acrylic acids has been developed. The reaction uses inexpensive organic dye 9,10-dicyanoanthracene as a photocatalyst and uses the ubiquitous dioxygen as both an oxygen source and an oxidant. Through this mild and environmentally friendly method, a series of important α-thiocyanate ketones can be generated from easily available acrylic acids and ammonium thiocyanate. In addition, the facile transformation of product α-thiocyanate ketones makes this method have great potential for application in organic and pharmaceutical chemistry.

VACCINE ADJUVANT

Compounds useful as an adjuvant, e.g., formulas (I)-(VI) and uses thereof, for example, with immunogenic moieties or other adjuvants, are provided.

Ag-Catalyzed Thiocyanofunctionalization of Terminal Alkynes to Access Alkynylthiocyanates and α-Thiocyanoketones

Unprecedented one-pot thiocyanofunctionalizations of terminal alkynes to deliver alkynylthiocyanates and α-thiocyanoketones using a silver-catalyzed procedure or under silver/gold relay catalysis is reported. These synthetically valuable organothiocyanates are accessed in high efficiency, and their derivatization into a variety of valuable sulfur-containing heterocycles and sulfides has also been demonstrated.