102804-82-0

Basic information

• Product Name: 2-[(4-METHOXY-3-METHYL-2-PYRIDINYL)-METHYLTHIO]-BENZIMIDAZOLE
• Synonyms: 2-[(4-METHOXY-3-METHYL-2-PYRIDINYL)-METHYLTHIO]-BENZIMIDAZOLE;2-{[(4-Methoxy-3-Methylpyridin-2-yl)Methyl]sulfanyl}-1H-1,3-benzodiazole;4-DesMethoxypropoxyl-4-Methoxy S-Deoxo Rabeprazole;Rabeprazole EP Impurity G;Rabeprazole Impurity 5;Rabeprazolesodium Impurity R
• CAS NO: 102804-82-0
• Molecular Formula: C₁₅H₁₅N₃OS
• Molecular Weight: 285.36
• Product Categories: Aromatics, Heterocycles, Impurities, Metabolites & Impurities, Sulfur & Selenium Compounds
• Mol File: 102804-82-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 504.7±60.0 °C(Predicted)
• Appearance: /
• Density: 1.30±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 10.60±0.10(Predicted)
• CAS DataBase Reference: 2-[(4-METHOXY-3-METHYL-2-PYRIDINYL)-METHYLTHIO]-BENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(4-METHOXY-3-METHYL-2-PYRIDINYL)-METHYLTHIO]-BENZIMIDAZOLE(102804-82-0)
• EPA Substance Registry System: 2-[(4-METHOXY-3-METHYL-2-PYRIDINYL)-METHYLTHIO]-BENZIMIDAZOLE(102804-82-0)

Safety Data

• Hazardous Substances Data: 102804-82-0(Hazardous Substances Data)

Usage

Description

2-[(4-METHOXY-3-METHYL-2-PYRIDINYL)-METHYLTHIO]-BENZIMIDAZOLE is a light brown solid with a complex chemical structure, characterized by its unique combination of pyridine, benzimidazole, and methylthio groups. 2-[(4-METHOXY-3-METHYL-2-PYRIDINYL)-METHYLTHIO]-BENZIMIDAZOLE is known for its potential applications in the pharmaceutical industry, particularly in the development of anti-Helicobacter pylori agents.

Uses

Used in Pharmaceutical Industry:
2-[(4-METHOXY-3-METHYL-2-PYRIDINYL)-METHYLTHIO]-BENZIMIDAZOLE is used as a key intermediate in the synthesis of 2-[[(2-pyridyl)methyl]thio]-1H-benzimidazoles derivatives, which are known for their anti-Helicobacter pylori properties. Helicobacter pylori is a bacterium that can cause various gastrointestinal issues, including peptic ulcers and gastritis. The development of effective agents against this bacterium is crucial for improving treatment options and patient outcomes.
Application Reason:
The compound's unique chemical structure allows it to interact with specific targets in Helicobacter pylori, inhibiting its growth and reducing its ability to cause harm in the gastrointestinal tract. This makes it a valuable component in the development of new drugs and therapies for treating H. pylori infections.

Upstream product

• 102625-98-9 2-acetoxymethyl-4-methoxy-3-methylpyridine 
• 134469-07-1 Benzimidazol-2-thiol 
• 102625-96-7 4-methoxy-2,3-dimethylpyridine 1-oxide 
• 86604-77-5 2-hydroxymethyl-4-methoxy-3-methylpyridine 
• 59886-90-7 4-chloro-2,3-dimethylpyridine-N-oxide 
• 37699-43-7 2,3-dimethyl-4-nitropyridine N-oxide 
• 86604-74-2 2-chloromethyl-4-methoxy-3-methylpyridine hydrochloride 
• 124473-12-7 2-chloromethyl-3-methyl-4-methoxypyridine 

Downstream Products

• 131926-97-1 demethoxypropylrabeprazole thioether 
• 102804-77-3 2-[(RS)-[(4-methoxy-3-methylpyridin-2-yl)methyl]sulfinyl]-1H-benzimidazole 

Relevant articles and documents

HELICOBACTER PYLORI ERADICATING AGENT HAVING INHIBITORY ACTIVITY ON GASTRIC ACID SECRETION

Disclosed are: a compound which is stable in an acid, has an antibacterial effect against a bacterium Helicobacter pylori, can exert a satisfactory level of an antibacterial effect when used singly, does not affect an enteric bacterium, has an antibacterial effect against a bacterium resistant to an antibacterial agent, and has an inhibitory effect on gastric acid secretion; and a pharmaceutical composition comprising the compound. Specifically disclosed are: a compound represented by the general formula (I) or a salt thereof; and a pharmaceutical composition comprising the compound or the salt thereof: wherein R represents a linear alkyl group having 4 to 8 carbon atoms, preferably 5 to 7 carbon atoms.

Structure-activity relationship of 2-[[(2-Pyridyl)methyl]thio]-1H- benzimidazoles as anti Helicobacter pylori agents in vitro and evaluation of their in vivo efficacy

A relationship between the structure of 21 2-[[(2-pyridyl)methyl]thio]- 1H-benzimidazoles (6) and their anti Helicobacter pylori activity expressed as minimum bactericidal concentration (MBC) values is described. Observed MBCs ranged from 256 to 1 μg/mL. The structure - activity relationship (SAR) showed that larger and more lipophilic compounds, especially compounds with such substituents in the 4-position of the pyridyl moiety, generally had lower MBC values. Four new compounds 'that were predicted to be potent by the established SAR model were synthesized and tested. One such compound, i.e., 2-[[(4-[(cyclopropylmethyl)oxy]3-methyl-2-pyridyl)methyl]thio]-1H- benzimidazole (18), was tested for in vivo efficacy in a mouse Helicobacter felis model (125 μmol/kg bid given orally for 4 days, n = 4). Unfortunately, antibacterial activity could not be clearly demonstrated in this model. Instead a potent acid secretion inhibition was observed. This finding was attributed to the methylthio compound being oxidized to the corresponding methyl sulfinyl derivative, i.e., a proton pump inhibitor, in vivo. Although the antibacterial activity had the potential of decreasing H. felis cell counts in vivo the proton pump inhibitory effect became dominant and actually promoted H. felis cell growth. Hence, we conclude that the antibacterial utility of the 2-[[(2-pyridyl)methyl]thio]1H-benzimidazoles (6) as a compound class is compromised by their propensity to become proton pump inhibitors upon metabolic oxidation in vivo.