128430-54-6

Basic information

• Product Name: 4-cyclopropylmethoxy-2-methylpyridine-1-oxide
• Synonyms: 4-cyclopropylmethoxy-2-methylpyridine-1-oxide
• CAS NO: 128430-54-6
• Molecular Weight: 179.219
• Mol File: 128430-54-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-cyclopropylmethoxy-2-methylpyridine-1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-cyclopropylmethoxy-2-methylpyridine-1-oxide(128430-54-6)
• EPA Substance Registry System: 4-cyclopropylmethoxy-2-methylpyridine-1-oxide(128430-54-6)

Safety Data

• Hazardous Substances Data: 128430-54-6(Hazardous Substances Data)

Upstream product

• 5470-66-6 2-methyl-4-nitropyridine N-oxide 
• 2516-33-8 Cyclopropylmethanol 

Relevant articles and documents

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.

Therapeutically active fluoro substituted benzimidazoles

The novel compounds of the formulas I and I' STR1 wherein F is in 5 or 6 position and STR2 wherein in both formulas R is the group --CH2 OCOOR1, wherein R1 is a straight or branched alkyl containing 1-6 carbon atoms or benzyl, or R1 is the group STR3 --(CH2)n COOH or --(CH2)n SO3 H wherein n is 1-6 and physiologically acceptable salts thereof as well as intermediates, pharmaceutical compositions containing such compounds as active ingredient, and the use of the compounds in medicine.