23593-74-0

Upstream product

• 51-17-2 benzoimidazole 
• 224294-34-2 4-(2-fluorostyryl)-6-fluorocoumarin 
• 87268-78-8 2-trityl-5-phenyl-2H-tetrazole 
• 76-83-5 trityl chloride 
• 1418363-64-0 2-iodo-1-trityl-1H-benzimidazole 
• 4887-88-1 6-bromo-1H-benzo[d]imidazole 
• 110-85-0 piperazine 
• 247083-09-6 6-bromo-1-trityl-1H-benzo[d]imidazole 

Downstream Products

• 191542-38-8 2-(phenylsulfanyl)-1-(triphenylmethyl)benzimidazole 
• 191542-45-7 1-<5-(phenylselanyl)pentyl>-2-(phenylsulfanyl)-1H-benzimidazole 
• 191542-44-6 1-<4-(phenylselanyl)butyl>-2-(phenylsulfanyl)-1H-benzimidazole 
• 191542-43-5 1-<3-(phenylselanyl)propyl>-2-(phenylsulfanyl)-1H-benzimidazole 
• 7724-48-3 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole 
• 2360-29-4 2-(phenylsulfanyl)-1H-benzimidazole 
• 19979-46-5 7,8,9,10-tetrahydro-6H-benzo[4,5]imidazo[1,2-a]azepine 
• 5622-83-3 1,2,3,4-tetrahydro-pyrido[1,2-a]benzimidazole 

Relevant academic research and scientific papers

1,(3,)5-substituted imidazoles, useful in the treatment of hypertension and methods for their preparation

The present invention provides novel 1,5 and 1,3,5-substituted imidazole compounds in hydrophilic or lipophilic form, which are useful as angiotensin II ATI receptor antagonists suitable for transdermal delivery. The invention also provides pharmaceutical compositions containing such compounds, processes and intermediates for preparing compounds and their use in methods of treating hypertension and cardiovascular diseases.

Access to aromatic ring-fused benzimidazoles using photochemical substitutions of the benzimidazol-2-yl radical

Photochemical five-, six-, and seven-membered cyclizations from 2-iodo-1-(ω-arylalkyl)-1H-benzimidazoles are described. This method of producing aromatic ring-fused benzimidazoles is significantly more efficient than literature radical protocols using chemical initiators, although 2-iodo-1-(ω-pyridin-2-ylalkyl)-1H-benzimidazoles preferentially undergo a nucleophilic ipso-substitution onto the benzimidazole-2-position.

Access to aromatic ring-fused benzimidazoles using photochemical substitutions of the benzimidazol-2-yl radical

Photochemical five-, six-, and seven-membered cyclizations from 2-iodo-1-(ω-arylalkyl)-1H-benzimidazoles are described. This method of producing aromatic ring-fused benzimidazoles is significantly more efficient than literature radical protocols using chemical initiators, although 2-iodo-1-(ω-pyridin-2-ylalkyl)-1H-benzimidazoles preferentially undergo a nucleophilic ipso-substitution onto the benzimidazole-2-position. Georg Thieme Verlag Stuttgart - New York.

First selective CYP11B1 inhibitors for the treatment of cortisol-dependent diseases

Outgoing from an etomidate-based design concept, we succeeded in the development of a series of highly active and selective inhibitors of CYP11B1, the key enzyme of cortisol biosynthesis, as potential drugs for the treatment of Cushing's syndrome and rela

Benzimidazoles as ligands in the ruthenium-catalyzed enantioselective bifunctional hydrogenation of ketones

A series of Cl2Ru(diphosphane)L2 (II) complexes in which L = N1-alkylated benzimidazoles, bonding to the metal through nitrogen, have been synthesized and characterized. In the case of 1-methylbenzimidazole, the resulting complexes exist as statistical mixtures of all possible conformational isomers. When the size of the substituent on the benzimidazole was increased to complexes could be prepared that exist as a single diastereomer. All complexes possessing benzimidazole ligands bound to the ruthenium center are active for the mild and chemoselective hydrogenation of ketones in the presence of alkenes. Catalysts that exist as a single diastereomer, prepared with enantiomerically pure diphosphanes, catalyze the hydrogenation of prochiral ketones with moderate levels of enantioselectivity that are significantly improved relative to catalysts existing in several conformations.

1,(3,)5-SUBSTITUTED IMIDAZOLES, THEIR USE IN THE TREATMENT OF HYPERTENSION AND METHODS FOR THEIR PREPARATION

The present invention provides novel 1,5 and 1,3,5-substituted imidazole compounds in hydrophilic or lipophilic form, which are useful as angiotensin II ATI receptor antagonists suitable for transdermal delivery. The invention also provides pharmaceutical compositions containing such compounds, processes and intermediates for preparing compounds and their use in methods of treating hypertension and cardiovascular diseases.

Tetrazoles: XLIV. Synthesis and chemical properties of 5-substituted 2-triphenylmethyltetrazoles

Tritylation of tetrazole and its 5-substituted derivatives with triphenylmethyl chloride under conditions of phase-transfer catalysis regioselectively yields the corresponding 5-substituted 2-trityltetrazoles which can be used to protect N-H bonds in nitrogen-containing heterocycles and O-H bonds in primary alcohols. Thermolysis of 2-trityltetrazoles in benzonitrile leads to 3,6-disubstituted 1,2,4,5-tetrazines. Thermal transformation of the same compounds in dodecane follows a radically different mechanism, resulting in formation of difficultly accessible 8,8-diphenylheptafulvenes. The structure of the latter was proved by X-ray analysis.

Synthesis of new (benzimidazolyl)piperazines with affinity for the 5- HT(1A) receptor via Pd(0) amination of bromobenzimidazoles

The synthesis of a new family of (benzimidazolyl)piperazines has been developed through Pd(0) mediated amination of 4- and 6-bromobenzimidazole derivatives. Preliminary studies showed that some of these compounds are potent 5-HT(1A) receptor ligands.

Radical cyclisation onto imidazoles and benzimidazoles

New synthetic methodology has been developed for the synthesis of [1,2- a]fused imidazoles and benzimidazoles using intramolecular homolytic aromatic substitution. In the intramolecular substitution, N-(ω-alkyl) radicals are generated using Bu3SnH from N-(ω-phenylselanyl)alkyl side chains. Phenylselanyl groups are used as radical leaving groups to avoid problems in the N-alkylation of imidazoles and benzimidazoles. Arylsulfones for imidazoles, and phenylsulfides for benzimidazoles, are used at the leaving groups in the homolytic substitutions.

Influence of some novel N-substituted azoles and pyridines on rat hepatic CYP3A activity

A series of N-substituted heteroaromatic compounds structurally related to clotrimazole was synthesized, and the effects of these compounds on ethosuximide clearance in rats were determined as a measure of their abilities to induce cytochrome P4503A (CYP3A) activity. Ethosuximide clearance and in vitro erythromycin N-demethylase activity were shown to correlate. In this series, imidazole or other related heteroaromatic 'head groups' were linked to triphenylmethane or other phenylmethane derivatives. Within the series, it was found that 1-triphenylmethane-substituted imidazoles elicited the greatest increase in CYP3A activity, and that among the triphenylmethyl-substituted imidazoles, the highest activities were achieved by the substitution of F- or Cl- in either the meta or para position of one of the phenyl rings. Diphenylmethylsubstituted pyridine was effectively devoid of activity. Compounds eliciting the largest increase in CYP3A activity (viz. 1-[(3-fluorophenyl)diphenylmethyl]imidazole, 1-[(4- fluorophenyl)diphenylmethyl]imidazole, and 1-[tri-(4- fluorophenyl)methyl]imidazole) produced little or no increase in ethoxyresorufin O-dealkylase (EROD) activity (i.e. CYP1A), whereas benzylimidazole, which elicited only a small increase in CYP3A activity, produced an almost 9-fold increase in CYP1A activity. For a series of eleven compounds exhibiting a wide range of influence on CYP3A activity, a positive correlation was found between ethosuximide clearance and hepatic CYP3A mRNA levels.