27428-57-5

Usage

Purification Methods

Crystallise the phenone from EtOH or *C6H6 and further purify it by zone refining (100 passes) [Grove & Turner J Chem Soc 509 1929, Lin & Hanson J Phys Chem 91 2279 1987]. [Beilstein 7 II 360, 7 III 2081.]

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

Upstream product

• 108-86-1 bromobenzene 
• 122-01-0 4-chloro-benzoyl chloride 
• 108-90-7 chlorobenzene 
• 586-75-4 4-chlorobenzoyl chloride 
• 855751-15-4 1,2-bis-(4-bromo-phenyl)-1,2-bis-(4-chloro-phenyl)-ethene 
• 64-19-7 acetic acid 
• 872820-48-9 (4-bromo-4'-chloro-trityl)-chloro-amine 
• 201230-82-2 carbon monoxide 
• 589-87-7 1,4-bromoiodobenzene 
• 1679-18-1 4-Chlorophenylboronic acid 
• 17151-48-3 tributyl(4-chlorophenyl)stannane 
• 106-37-6 1.4-dibromobenzene 
• 122334-37-6 4-chloro-N-methoxy-N-methylbenzamide 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 81223-63-4 dioxolanne de la chloro-4 bromo-4' benzophenone 
• 81223-65-6 4-(4-chlorobenzoyl)benzaldehyde 
• 81223-74-7 p-chlorobenzoyl-6 indole 
• 81223-64-5 dioxolanne du p-chlorobenzoyl-4 benzaldehyde 
• 81223-72-5 acide p-chlorobenzoyl-6 indolecarboxylique-2 
• 81223-94-1 p-chlorobenzoyl-6 N,N-dimethyl gramine 
• 81223-97-4 acide p-chlorobenzoyl-6 indoleacetique-3 
• 81223-69-0 p-chlorobenzoyl-6 indolecarboxylate-2 de methyle 
• 81223-86-1 ethoxycarbonyl-1 p-chlorobenzoyl-6 indole 
• 81223-67-8 (azido-2 p-chlorobenzoyl-6) cinnamate de methyle 
• 81223-88-3 p-chlorobenzoyl-6 indolyl-1 acetate d'ethyle 
• 81223-78-1 (methyl-4' benzenesulfonyl)-1 p-chlorobenzoyl-6 indole 
• 1063739-26-3 2-(4-bromophenyl)-4-chloromethyl-2-(4-chlorophenyl)-1,3-dioxolane 
• 1220124-27-5 [(4-bromophenyl)-(4-chlorophenyl)ketone]thiosemicarbazone 

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.

AIBN initiated functionalization of the benzylic sp3 C[sbnd]H and C[sbnd]C bonds in the presence of dioxygen

A sp3 C[sbnd]H bond functionalization and C[sbnd]C bond cleavage were realized by AIBN/O2 catalyst system, providing a series of benzophenones under mild reaction conditions. The mechanistic study shows that a peroxide intermediate is involved in this transformation, and in the case of diphenylmethanes, the sp3 C[sbnd]C bond is cleaved through the peroxide rearrangement, which might provides a new way to cleave relatively strong C[sbnd]C bond and be applied to more general C[sbnd]C bond activation.

Synthesis of biaryl ketones by arylation of Weinreb amides with functionalized Grignard reagents under thermodynamic controlvs.kinetic control ofN,N-Boc2-amides

A highly efficient method for chemoselective synthesis of biaryl ketones by arylation of Weinreb amides (N-methoxy-N-methylamides) with functionalized Grignard reagents is reported. This protocol offers rapid entry to functionalized biaryl ketones after Mg/halide exchange with i-PrMgCl·LiCl under operationally-simple and practical reaction conditions. The scope of the method is highlighted in >40 examples, including bioactive compounds and pharmaceutical derivatives. Collectively, this transition-metal-free approach offers a major advantage over the recently established cross-coupling of amides by oxidative addition of N-C(O) bonds. Considering the utility of amide acylation reactions in modern synthesis, we expect that this method will be of broad interest.

A combinational molecular design to achieve highly efficient deep-blue electrofluorescence

A deep-blue emitter 1-(10-(4-methoxyphenyl)anthracen-9-yl)-4-(10-(4-cyanophenyl)anthracen-9-yl)tetraphenylethene (TPEA) has been successfully prepared by a combinational molecular design, which contains triplet-triplet fusion (TTF) and hybridized local ch

Phosphine-Free, Heterogeneous Palladium-Catalyzed Atom-Efficient Carbonylative Cross-Coupling of Triarylbismuths with Aryl Iodides: Synthesis of Biaryl Ketones

A novel and highly efficient heterogeneous palladium-catalyzed carbonylative cross-coupling of aryl iodides with triarylbismuths has been developed that proceeds smoothly at atmospheric CO pressure and provides a general and powerful tool for the preparation of various valuable biaryl ketones with high atom economy, good to excellent yield, and recyclability of the catalyst. The reaction is the first example of Pd-catalyzed carbonylative cross-coupling for the construction of biaryl ketones using triarylbismuths as substrates.

Palladium(II)-catalyzed desulfitative synthesis of aryl ketones from sodium arylsulfinates and nitriles: Scope, limitations, and mechanistic studies

A fast and efficient protocol for the palladium(II)-catalyzed production of aryl ketones from sodium arylsulfinates and various organic nitriles under controlled microwave irradiation has been developed. The wide scope of the reaction has been demonstrated by combining 14 sodium arylsulfinates and 21 nitriles to give 55 examples of aryl ketones. One additional example illustrated that, through the choice of the nitrile reactant, benzofurans are also accessible. The reaction mechanism was investigated by electrospray ionization mass spectrometry and DFT calculations. The desulfitative synthesis of aryl ketones from nitriles was also compared to the corresponding transformation starting from benzoic acids. Comparison of the energy profiles indicates that the free energy requirement for decarboxylation of 2,6-dimethoxybenzoic acid and especially benzoic acid is higher than the corresponding desulfitative process for generating the key aryl palladium intermediate. The palladium(II) intermediates detected by ESI-MS and the DFT calculations provide a detailed understanding of the catalytic cycle. (Figure Presented).

Analogues of fenarimol are potent inhibitors of trypanosoma cruzi and are efficacious in a murine model of chagas disease

We report the discovery of nontoxic fungicide fenarimol (1) as an inhibitor of Trypanosoma cruzi (T. cruzi), the causative agent of Chagas disease, and the results of structure-activity investigations leading to potent analogues with low nM IC50s in a T. cruzi whole cell in vitro assay. Lead compounds suppressed blood parasitemia to virtually undetectable levels after once daily oral dosing in mouse models of T. cruzi infection. Compounds are chemically tractable, allowing rapid optimization of target biological activity and drug characteristics. Chemical and biological studies undertaken in the development of the fenarimol series toward the goal of delivering a new drug candidate for Chagas disease are reported.

Facile preparation of aromatic ketones from aromatic bromides and arenes with aldehydes

Aromatic ketones were efficiently prepared in good yields by the reactions of aryl bromides with n-BuLi, followed by the reactions with aromatic aldehydes or aliphatic aldehydes and the subsequent treatment with molecular iodine and K2CO3, in a one-pot method. The same treatment of arenes, instead of aromatic bromides, also provided the corresponding aromatic ketones in good yields. Using these methods, various diaryl ketones and alkyl aryl ketones bearing electron-rich aromatics and electron-deficient aromatics could be prepared efficiently by a simple, transition-metal-free, and therefore environmentally benign experimental procedure.

A phosphine-free carbonylative cross-coupling reaction of aryl iodides with arylboronic acids catalyzed by immobilization of palladium in MCM-41

The phosphine-free heterogeneous carbonylative cross-coupling of aryl iodides with arylboronic acids under an atmospheric pressure of carbon monoxide was achieved in anisole at 80 °C in the presence of a 3-(2-aminoethylamino) propyl-functionalized MCM-41-immobilized palladium(ii) complex [MCM-41-2N-Pd(ii)], yielding a variety of unsymmetrical biaryl ketones in good to high yield. This heterogeneous palladium catalyst exhibited higher activity and selectivity than PdCl2(PPh3)2, can be recovered and recycled by a simple filtration of the reaction solution, and used for at least 10 consecutive trials without any decrease in activity. Our system not only avoids the use of phosphine ligands, but also solves the basic problem of palladium catalyst recovery and reuse.

Design, synthesis, and biological evaluation of potent thiosemicarbazone based cathepsin L inhibitors

A small library of 36 functionalized benzophenone thiosemicarbazone analogs has been prepared by chemical synthesis and evaluated for their ability to inhibit the cysteine proteases cathepsin L and cathepsin B. Inhibitors of cathepsins L and B have the potential to limit or arrest cancer metastasis. The six most active inhibitors of cathepsin L (IC50 50 > 10,000 nM). The most active analog in the series, 3-bromophenyl-2′-fluorophenyl thiosemicarbazone 1, also efficiently inhibits cell invasion of the DU-145 human prostate cancer cell line.