464190-33-8

Usage

InChI:InChI=1/C13H8BrClO/c14-10-7-5-9(6-8-10)13(16)11-3-1-2-4-12(11)15/h1-8H

Upstream product

• 464190-32-7 (4-bromophenyl)(2-chlorophenyl)methanol 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 586-75-4 4-chlorobenzoyl chloride 
• 108-86-1 bromobenzene 
• 609-65-4 o-chlorobenzoyl chloride 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 89-98-5 2-chloro-benzaldehyde 

Relevant academic research and scientific papers

Identification and optimization of biphenyl derivatives as novel tubulin inhibitors targeting colchicine-binding site overcoming multidrug resistance

Microtubule targeting agents (MTAs) are among the most successful chemotherapeutic drugs, but their efficacy is often limited by the development of multidrug resistance (MDR). Therefore, the development of novel MTAs with the ability to overcome MDR is urgently needed. In this contribution, through modification of the unsymmetric biaryl compounds, we discovered a novel compound dxy-1-175 with potent anti-proliferative activity against cancer cells. Mechanistic study revealed that dxy-1-175 inhibited tubulin polymerization by interacting with the colchicine-binding site of tubulin, which caused cell cycle arrest at G2/M phase. Based on the predicted binding model of dxy-1-175 with tubulin, a series of new 4-benzoylbiphenyl analogues were designed and synthesized. Among them, the hydrochloride compound 12e with improved solubility and good stability in human liver microsome, exhibited the most potent anti-proliferative activity with IC50 value in the low nanomolar range, and markedly inhibited the growth of breast cancer 4T1 xenograft in vivo. Notably, 12e effectively overcame P-gp-mediated MDR and our preliminary data suggested that 12e may not be a substrate of P-glycoprotein (P-gp). Taken together, our study reveals a novel MTA 12e targeting the colchicine-binding site with potent anticancer activity and the ability to circumvent MDR.

Catalytic Friedel-Crafts acylation: Magnetic nanopowder CuFe 2O4 as an efficient and magnetically separable catalyst

Catalytic regioselective Friedel-Crafts acylation of an array of anisoles/arenes with various acid chlorides using 5-20 mol % of magnetic nanopowder CuFe2O4 is reported. Unlike the conventional Friedel-Crafts reactions, which are catalyzed by moisture sensitive homogeneous catalysts/promoters, the nanopowder CuFe2O4 catalyst is moisture insensitive and the product/ketone-catalyst isolation is easily achieved using the magnetic properties of CuFe2O4.

Insertion of arynes into carbon-halogen σ-bonds: Regioselective acylation of aromatic rings

Arynes were found to insert into carbon-halogen σ-bonds of various acid halides, enabling acyl and halogen moieties to be introduced simultaneously into adjacent positions of aromatic rings. The Royal Society of Chemistry.

SAR of benzoylpyridines and benzophenones as p38α MAP kinase inhibitors with oral activity

Benzoylpyridines and benzophenones were synthesized and evaluated in vitro as p38α inhibitors and in vivo in several models of rheumatoid arthritis. Oral activity was found to depend upon substitution: 1,1-dimethylpropynylamine substituted benzophenone 10b (IC50: 14nM) and pyridinoyl substituted benzimidazole 17b (IC50: 21nM) showed highest efficacy and selectivity with ED50s of 9.5 and 8.6mg/kg po in CIA.