324546-94-3

Upstream product

• 68185-96-6 (4-(tert-butyl)phenyl)(trimethylsilyl)methanone 
• 1590361-11-7 O-diethylcarbamoyl-N-phenethylhydroxylamine 
• 1590361-20-8 N-tert-butoxycarbonyl-O-diethylcarbamoyl-N-phenethylhydroxylamine 
• 103-63-9 1-phenyl-2-bromoethane 
• 64-04-0 phenethylamine 
• 1710-98-1 p-tert-butyl benzoyl chloride 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 939-97-9 4-tert-Butylbenzaldehyde 

Relevant academic research and scientific papers

Chemoselective Amide-Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions

We report the facile amide-forming ligation of acylsilanes with hydroxylamines (ASHA ligation) under aqueous conditions. The ligation is fast, chemoselective, mild, high-yielding and displays excellent functional-group tolerance. Late-stage modifications of an array of marketed drugs, peptides, natural products, and biologically active compounds showcase the robustness and functional-group tolerance of the reaction. The key to the success of the reaction could be the possible formation of the strong Si?O bond via a Brook-type rearrangement. Given its simplicity and efficiency, this ligation has the potential to unfold new applications in the areas of medicinal chemistry and chemical biology.

Design, Synthesis, and Biological Evaluation of Tetrahydroisoquinoline-Based Histone Deacetylase 8 Selective Inhibitors

Histone deacetylase 8 (HDAC8) is a promising drug target for multiple therapeutic applications. Here, we describe the modeling, design, synthesis, and biological evaluation of a novel series of C1-substituted tetrahydroisoquinoline (TIQ)-based HDAC8 inhibitors. Minimization of entropic loss upon ligand binding and use of the unique HDAC8 "open" conformation of the binding site yielded a successful strategy for improvement of both HDAC8 potency and selectivity. The TIQ-based 3g and 3n exhibited the highest 82 and 55 nM HDAC8 potency and 330- and 135-fold selectivity over HDAC1, respectively. Selectivity over other class I isoforms was comparable or better, whereas inhibition of HDAC6, a class II HDAC isoform, was below 50% at 10 μM. The cytotoxicity of 3g and 3n was evaluated in neuroblastoma cell lines, and 3n displayed concentration-dependent cytotoxicity similar to or better than that of PCI-34051. The selectivity of 3g and 3n was confirmed in SH-SY5Y cells as both did not increase the acetylation of histone H3 and α-tubulin. Discovery of the novel TIQ chemotype paves the way for the development of HDAC8 selective inhibitors for therapeutic applications.

Zinc(II)-catalyzed oxidative amidation of arylaldehydes with alkylamines under solvent-free conditions

The first zinc-catalyzed oxidative amidation of arylaldehydes has been developed. Various amides were prepared in good yields under solvent-free and mild reaction conditions.