15088-30-9

Usage

InChI:InChI=1/C18H24N2O2/c21-17(19-11-3-1-4-12-19)15-7-9-16(10-8-15)18(22)20-13-5-2-6-14-20/h7-10H,1-6,11-14H2

Upstream product

• 110-89-4 piperidine 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 100-20-9 terephthaloyl chloride 
• 100-21-0 terephthalic acid 
• 623-27-8 terephthalaldehyde, 
• 2669-15-0 N,N'-terephthaloylbis(6-hexanelactam) 

Downstream Products

• 36997-13-4 1,4-bis(piperidin-1-ylmethyl)benzene 

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.

Cesium carbonate-catalyzed reduction of amides with hydrosilanes

Cesium carbonate has been found to be an effective catalyst for the reduction of tertiary carboxamides with the simple, commercially available PhSiH3 under solvent-free conditions. The catalytic system can effectively reduce a range of amides under relatively mild conditions (from room temperature to 80 C) to yield the corresponding amines in good to excellent yields (71-100%) and thus has the potential for practical applications.

Gold-catalyzed amide synthesis from aldehydes and amines in aqueous medium

An efficient gold-catalyzed amide synthesis from aldehydes and amines in aqueous medium under mild reaction conditions has been developed.

Crystal structures of seven terephthaldiamide derivatives

N,N′-Dibutyl-terephthaldiamide (1), N,N′-dihexyl-terephthaldiamide (2), N,N′-di(tert-butyl)-terephthaldiamide (3), N,N,N′,N′-tetrabutyl-terephthaldiamide (4), 1,1′-terephthaloyl-bis-pyrrolidine (5), 1,1′-terephthaloyl-bis-piperidine (6), and 4,4′-terephthaloyl-bis-morpholine (7) have been synthesised and physicochemically characterised. The X-ray structure determinations reveal imposed inversion symmetry for compounds 1-6; compound 3 has two independent molecules with inversion symmetry in the asymmetric unit. Compounds 1-3 form classical hydrogen bonds of the type N-H?O=C, leading to a ribbon-like arrangement of molecules (1 and 2) or a layer structure (3). Compound 3 also displays a very short C-H?O interaction, a type of hydrogen bond that is also observed in compounds 4-7, which lack classical donors; thereby compounds 4-6 form layer structures and 7 a complex three-dimensional network.

Aminolysis of N-acyllactams

The overall second-order rate constants of aminolysis of N-benzoyllactams of different ring size, the rate constants of aminolysis of N,N'-isophthaloyl- and N,N'-terephthaloylbis(6-hexanelactam) to the first and second stages and the ratio of splitting of the exocyclic and endocyclic amide bond by octylamine were determined in THF at 50 deg C.The effect of the type of amine and medium on the rate of aminolysis was examined.