87853-73-4

Upstream product

• 87853-74-5 (2-bromophenyl)(3,4-dimethoxyphenyl)amine 
• 16668-99-8 bis(phenyl)iodonium trifluoroacetate 
• 6315-89-5 3,4-dimethoxyaniline 
• 2859-78-1 4-Bromoveratrole 
• 62-53-3 aniline 
• 591-50-4 iodobenzene 
• 87853-81-4 N-(2-bromophenyl)-N-(3,4-dimethoxyphenyl)formamide 
• 87853-76-7 2-bromo-N-(3,4-dimethoxybenzylidene)aniline N-oxide 
• 35758-75-9 N-(2-bromophenyl)hydroxylamine 

Relevant academic research and scientific papers

Investigation of B,C-ring truncated deguelin derivatives as heat shock protein 90 (HSP90) inhibitors for use as anti-breast cancer agents

On the basis of deguelin, a series of the B,C-ring truncated surrogates with N-substituted amide linkers were investigated as HSP90 inhibitors. The structure activity relationship of the template was studied by incorporating various substitutions on the nitrogen of the amide linker and examining their HIF-1α inhibition. Among them, compound 57 showed potent HIF-1α inhibition and cytotoxicity in triple-negative breast cancer lines in a dose-dependent manner. Compound 57 downregulated expression and phosphorylation of major client proteins of HSP90 including AKT, ERK and STAT3, indicating that its antitumor activity was derived from the inhibition of HSP90 function. The molecular modeling of 57 demonstrated that 57 bound well to the C-terminal ATP-binding pocket in the open conformation of the hHSP90 homodimer with hydrogen bonding and pi-cation interactions. Overall, compound 57 is a potential antitumor agent for triple-negative breast cancer as a HSP90 C-terminal inhibitor.

Discovery of Conformationally Restricted Human Glutaminyl Cyclase Inhibitors as Potent Anti-Alzheimer's Agents by Structure-Based Design

Alzheimer's disease (AD) is an incurable, progressive neurodegenerative disease whose pathogenesis cannot be defined by one single element but consists of various factors; thus, there is a call for alternative approaches to tackle the multifaceted aspects of AD. Among the potential alternative targets, we aim to focus on glutaminyl cyclase (QC), which reduces the toxic pyroform of β-amyloid in the brains of AD patients. On the basis of a putative active conformation of the prototype inhibitor 1, a series of N-substituted thiourea, urea, and α-substituted amide derivatives were developed. The structure-activity relationship analyses indicated that conformationally restrained inhibitors demonstrated much improved QC inhibition in vitro compared to nonrestricted analogues, and several selected compounds demonstrated desirable therapeutic activity in an AD mouse model. The conformational analysis of a representative inhibitor indicated that the inhibitor appeared to maintain the Z-E conformation at the active site, as it is critical for its potent activity.

Spirocentric Compounds and Polymers Thereof

The present invention is directed to novel functionalized spirocentric compounds and polymers thereof that produce hyper-rigid cross-linked membranes.

Arylation of anilines: formation of diarylamines using diaryliodonium salts

Extensive studies on the reaction of the fluoride ion with diaryliodonium salts demonstrated that this is a generic process for the formation of fluoroarenes and has particular advantages for the preparation of fluorine-18 radiopharmaceuticals. During these studies it became apparent that nucleophiles other than the fluoride ion may be employed for generating substituted aromatics. This approach can be applied, using substituted anilines as the nucleophilic reagent, to the formation of a range of diarylamines in good yield. Optimised conditions for the reaction of a diaryliodonium salt with an aniline utilise TFA as the preferred counter-ion in DMF (130 °C, 24 h).

Process for producing diphenylamines or N,N'-diphenyl-phenylenediamines

Diphenylamines or N,N'-diphenyl-phenylenediamines can be obtained by heat-reacting an aniline or a phenylenediamine with preferably an excess of a phenol in an amount of 4 to 20 moles per mole of the aniline or phenylenediamine in the presence of a hydrogen transfer catalyst and a cyclohexanone corresponding to said phenol. The excess phenol used in the reaction undergoes reduction in the reaction system to form a cyclohexanone, which in turn reacts with the aniline or phenylenediamine to form a Schiff base and is thus consumed. The Schiff base forms the intended product by means of a dehydrogenation reaction, and the hydrogen evolved at this time reduces the phenol to form a cyclohexanone. The phenol present in excess thus becomes in the system a solvent, a starting material for the cyclohexanone, and an acceptor of the hydrogen that forms as a by-product at the time of formation of the intended product. Hence, it becomes possible to obtain the intended product at a high selectivity from the anilines and phenylenediamines. The process of this invention is an advantageous process for the industrial production of especially the nuclearly substituted diphenylamines.

A 'Classical' Approach to the Synthesis of Perloline

An approach to the synthesis of perloline by the reaction of (2-bromophenyl)(3',4'-dimethoxyphenyl)amine with a suitably 4-substituted 2-oxo-1,2-dihydropyridine-3-carboxylic acid was unsuccessful due to the inability to form the amide bond.The diphenylamine was efficiently synthesized from the nitrone of dimethoxybenzylidene-2-bromoaniline via the oxaziridine, the thermal rearrangement of which was investigated.Conjugate additions of a diphenylamine dianion to unsaturated esters are reported.