53812-10-5

Upstream product

• 100-44-7 benzyl chloride 
• 578-46-1 5-methyl-2-nitroaniline 
• 100-39-0 benzyl bromide 
• 496-72-0 4-methyl-1,2-diaminobenzene 
• 100-46-9 benzylamine 
• 446-34-4 2-fluoro-4-methyl-1-nitrobenzene 

Downstream Products

• 53811-73-7 1-benzyl-2-furan-2-yl-6-methyl-1H-benzoimidazole 
• 53811-67-9 2-benzo[1,3]dioxol-5-yl-1-benzyl-6-methyl-1H-benzoimidazole 
• 53811-63-5 1-benzyl-6-methyl-2-(4-methylphenyl)-1H-benzimidazole 
• 1415650-64-4 1-benzyl-2-(4-(benzyloxy)phenyl)-6-methyl-1H-benzimidazole 
• 53811-70-4 6-methyl-2-(4-nitrophenyl)-1-benzyl-1H-benzo[d]imidazole 
• 24781-11-1 1-benzyl-6-methyl-2-phenyl-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

MRGX Receptor Antagonists

The invention relates to a method for preventing or treating a disease or disorder that is associated with the MrgX2 receptor. The invention also relates to MrgX2 antagonists and physiologically acceptable salts thereof. The invention also relates to pharmaceutical compositions and dosage forms comprising an MrgX2 antagonist.

Discovery and Characterization of Benzimidazole Derivative XY123 as a Potent, Selective, and Orally Available RORγ Inverse Agonist

Receptor-related orphan receptor γ (RORγ) has emerged as an attractive therapeutic target for the treatment of cancer and inflammatory diseases. Herein, we report our effort on the discovery, optimization, and evaluation of benzothiazole and benzimidazole derivatives as novel inverse agonists of RORγ. The representative compound27h(designated as XY123) potently inhibited the RORγ transcription activity with a half-maximal inhibitory concentration (IC50) value of 64 nM and showed excellent selectivity against other nuclear receptors.27halso potently suppressed cell proliferation, colony formation, and the expression of androgen receptor (AR)-regulated genes in AR-positive prostate cancer cell lines. In addition,27hdemonstrated good metabolic stability and a pharmacokinetic property with reasonable oral bioavailability (32.41%) and moderate half-life (t1/2= 4.98 h). Significantly, oral administration of compound27hachieved complete and long-lasting tumor regression in the 22Rv1 xenograft tumor model in mice. Compound27hmay serve as a new valuable lead compound for further development of drugs for the treatment of prostate cancer.

Synthesis of 1,2-disubstituted benzimidazoles through DDQ-oxidized intramolecular dehydrogenative coupling of N,N′-dialkyl o-phenylenediamines

The synthetic methodology of 1,2-disubstituted benzimidazoles has been developed, which starts from N,N′-dialkyl o-phenylenediamines via intramolecular dehydrogenative coupling under the oxidation of DDQ with mild conditions. Through detailed optimization of reaction conditions, only DDQ was found essential without any additives to reach to the highest yield of 99%. In the cases of linear aliphatic substituents, the synthesis of 1-alkyl-2-phenylbenzimidazoles showed high selectivities and their structures were identified by 2D NMR COSY correlation analysis. A plausible mechanism was proposed to interpret the observed reactivities and selectivities.

"All-water" one-pot diverse synthesis of 1,2-disubstituted benzimidazoles: Hydrogen bond driven 'synergistic electrophile-nucleophile dual activation' by water

A new "all-water" tandem arylaminoarylation/arylaminoalkylation- reduction-cyclisation route is reported for one-pot diversity oriented synthesis of regiodefined 1,2-disubstituted benzimidazoles. Water plays a crucial and indispensable role through hydrogen bond driven 'synergistic electrophile-nucleophile dual activation' in the formation of N-mono-aryl/aryl alkyl/alkyl/cycloalkyl o-nitroanilines under metal and base-free conditions to replace the transition metal-based C-N bond formation (aryl amination) chemistry and underlines the origin of regiodefined installation of the diverse selection of aryl, aryl alkyl, and alkyl/cycloalkyl groups as substituents on the benzimidazole scaffold to form the 1,2-disubstituted benzimidazoles. The influence of the hydrogen bond effect of water in promoting the arylaminoarylation reaction under base and metal-free conditions has been realized through observation of inferior yields in D2O compared to that obtained in water during the reaction of o-fluoronitrobenzene with aniline separately performed in water and D2O under similar experimental conditions. Water also provides assistance in promoting the subsequent nitro reduction and in the final cyclocondensation steps. The role of water in promoting the cyclocondensation reaction through hydrogen bonds is realized by the differential product yields during the reaction of mono-N-phenyl-o- phenylenediamine with benzaldehyde performed separately in water and D 2O. The better hydrogen bond donor and hydrogen bond acceptor abilities of water compared to those of the organic solvents are the contributing/deciding factors for making the new water-assisted tandem arylaminoarylation/arylaminoalkylation-reduction-cyclisation strategy for the diversified synthesis of the regiodefined 1,2-disubstituted benzimidazoles effective in an aqueous medium, making it represent a true "all-water chemistry."