92807-01-7

Usage

Structure

Heterocyclic compound containing a benzimidazole ring and a thione group

Uses

Commonly used in pharmaceutical research
Precursor or intermediate in the synthesis of various bioactive compounds
Potential pharmacological properties, including antiviral, antimicrobial, and antitumor activities
Derivatives being studied for potential as drug candidates for various diseases
Used in the production of specialty chemicals and in organic synthesis.

Upstream product

• 64375-41-3 methyl 2-mercaptobenzimidazole-5-carboxylate 
• 556-08-1 p-(acetylamino)benzoic acid 
• 63189-97-9 (4-amino-3-nitrophenyl)methanol 
• 6313-39-9 4-acetamido-3-nitro-benzoic acid methyl ester 
• 73166-06-0 4-(hydroxymethyl)-2-nitroacetanilide 
• 17012-22-5 methyl 4-acetamidobenzoate 
• 63189-98-0 1,2-diamino-4-hydroxymethylbenzene 
• 140-89-6 potassium ethyl xanthogenate 

Downstream Products

• 128429-80-1 [2-(4-Methoxy-3-methyl-pyridin-2-ylmethylsulfanyl)-1H-benzoimidazol-5-yl]-methanol 
• 299901-34-1 5-(t-butyldiphenylsilyloxymethyl)-2-mercaptobenzoimidazole 

Relevant academic research and scientific papers

1-N-AMINOBENZIMIDAZOLE DERIVATIVES

Provided are 1-N-aminobenzimidazole derivatives represented by the following formula (I): wherein R1 and R2 each represents a substituted or unsubstituted alkyl group or the like, R3, R5 and R6 each represents an alkyl group, alkoxy group, hydrogen atom or the like, R4 represents a substituted or unsubstituted alkyl group or the like, A represents a benzene ring or the like, B represents a hydrogen atom or the like, an n stands for an integer of from 0 to 2, or salts thereof; and medicines containing them. The compounds (I) according to the present invention do not bring about much individual differences in therapeutic effects despite the existence of individual differences in the CYP2C19 activity. At the same dose, they can hence bring about appropriate therapeutic effects for all patients. In addition, they are low in the risk of induction of an interaction or a cancer caused by induction of the CYP1A family. Accordingly, they are useful as peptic ulcer therapeutic agents which are safe and surely bring about therapeutic effects.

Structure-activity relationship of omeprazole and analogues as Helicobacter pylori urease inhibitors

Helicobacter pylori urease belongs to a family of highly conserved urea- hydrolyzing enzymes. A common feature of these enzymes is the presence of two Lewis acid nickel ions and a reactive cysteine residue in the active site. The H+/K+-ATPase inhibitor omeprazole is a prodrug of a sulfenamide which covalently modifies cysteine residues on the luminal side of the H+/K+- ATPase of gastric parietal cells. Omeprazole and eight analogues were selected based on their chemical, electronic, and kinetic properties, and each was incubated with viable H. pylori in phosphate-buffered saline at pH 7.4 for 30 min, after which 100 mM urea was added and the amount of ammonia formed analyzed after a further 10 min. Inhibition between 0% and 100% at a 0.1 mM concentration was observed for the different analogues and could be expressed as a function of the pK(a)-value of the pyridine, the pK(a)-value of the benzimidazole, the overall lipophilicity, and, most importantly, the rate of sulfenamide formation, in a quantitative structure-activity relationship. The inhibition was potentiated by a lower pH (favoring the formation of the sulfenamide) but abolished in the presence of β- mercaptoethanol (a scavenger of the sulfenamide). Structural analogues incapable of yielding the sulfenamide did not inhibit ammonia production. Treatment of Helicobacter felis-infected mice with 230 μmol/kg flurofamide b.i.d. for 4 weeks, known to potently inhibit urease activity in vivo, as a means of eradicating the infection, was tested and compared with the effect of 125 μmol/kg omeprazole b.i.d. for 4 weeks. Neither treatment proved efficacious.