38198-16-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloromethyl-4-methylpyridine is utilized as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of new molecules with potential therapeutic properties, making it an essential component in drug development.
Used in Agrochemical Industry:
In the agrochemical sector, 2-chloromethyl-4-methylpyridine is employed as a precursor in the production of agrochemicals. Its reactivity and ability to form stable derivatives make it suitable for the development of effective pesticides and other agricultural chemicals.
Used in Organic Synthesis:
As an intermediate in organic synthesis, 2-chloromethyl-4-methylpyridine is used to produce a range of other organic compounds. Its versatility in forming different chemical bonds and its compatibility with various solvents facilitate its use in creating diverse organic molecules for various applications.
Safety Precautions:
Given its toxic and flammable nature, 2-chloromethyl-4-methylpyridine requires careful handling and storage. It should only be manipulated by qualified individuals in a controlled laboratory setting, adhering to proper safety measures to prevent accidents and ensure the well-being of those involved in its use.

InChI:InChI=1/C7H8ClN/c1-6-2-3-9-7(4-6)5-8/h2-4H,5H2,1H3

Upstream product

• 42508-74-7 (4-methyl-2-pyridinyl)methanol 
• 1122-45-8 2,4-dimethylpyridine N-oxide 
• 74405-07-5 4-chloro-2,2-dimethyl-2H-benzo[e][1,3]oxazine 
• 98-59-9 p-toluenesulfonyl chloride 
• 55485-91-1 acetic acid 4-methyl-pyridin-2-ylmethyl ester 
• 108-47-4 2,4-lutidine 

Downstream Products

• 38746-50-8 4-methyl-2-pyridineacetonitrile 

Relevant academic research and scientific papers

Rapid and Effective Reaction of 2-Methylpyridin-N-oxides with Triphosgene via a [3,3]-Sigmatropic Rearrangement: Mechanism and Applications

A facile and effective synthesis of 2-chloromethylpyridines was developed by a one-pot reaction of 2-alkylpyridin-N-oxides and triphosgene at room temperature. As starting materials, N-oxides of 2-alkylpyridine derivatives, including 2-alkylpyridines, 2-methyl quinolines, and phenanthroline, can react rapidly with triphosgene in the presence of triethylamine, affording 2-chloromethylpyridines in good to excellent yields (52-95%). Using the 2-methylquinoline substrate for the mechanistic study, it has been well demonstrated that the chlorination reaction undergoes a [3,3]-sigmatropic rearrangement, which can be observed as a reversible process by monitoring the intermediates. Moreover, the chlorination reaction can be used to construct a rapid and sensitive fluorescent probe for the detection of phosgene.

Heterocycles substituted pyridine derivatives and antifungal agent containing thereof

An object of the present invention is to provide an antifungal agent which has excellent antifungal effects and is superior in terms of its physical properties, safety and metabolic stability. According to the present invention, there is disclosed a compound represented by the following formula (I), or a salt thereof: wherein R1 represents a hydrogen atom, a halogen atom, an amino group, a C1-6 alkyl group, a C1-6 alkoxy group or a C1-6 alkoxy C1-6 alkyl group; R2 represents a hydrogen atom, a C1-6 alkyl group, an amino group or a di C1-6 alkylamino group; one of X and Y is a nitrogen atom while the other is a nitrogen atom or an oxygen atom; ring A represents a 5- or 6-member heteroaryl ring or a benzene ring which may have a halogen atom, or 1 or 2 C1-6 alkyl groups; Z represents a single bond, a methylene group, an ethylene group, an oxygen atom, a sulfur atom, —CH2O—, —OCH2—, —NH—, —CH2NH—, —NHCH2—, —CH2S—, or —SCH2—; R3 represents a hydrogen atom, a halogen atom, a C1-6 alkyl group, a C3-8 cycloalkyl group, a C6-10 aryl group, a 5- or 6-member heteroaryl group, or 5- or 6-member non-aromatic heterocyclic group which may have 1 or 2 substituents; and R4 represents a hydrogen atom or a halogen atom.

Superoxide dismutase activity of iron(II)TPEN complex and its derivatives

Superoxide is involved in the pathogenesis of various diseases, such as inflammation, ischemia-reperfusion injury and carcinogenesis. Superoxide dismutases (SODs) catalyze the disproportionation reaction of superoxide to produce oxygen and hydrogen peroxide, and can protect living cells against the toxicity of free radicals derived from oxygen. Thus, SODs and their functional mimics have potential value as pharmaceuticals. We have previously reported that Fe(II)tetrakis-N,N,N',N'-(2-pyridylmethyl)ethylenediamine (Fe(II)TPEN) has an excellent SOD activity (IC50=0.5 μM) among many iron complexes examined (J. Biol. Chem., 264, 9243-9249 (1989)). Fe(II)TPEN can act like native SOD in living cells, and protect Escherichia coli cells from free radical toxicity caused by paraquat. In order to develop more effective SOD functional mimics, we synthesized Fe(II)TPEN derivatives with electron-donating or electron-withdrawing groups at the 4-position of all pyridines of TPEN, and measured the SOD activities and the redox potentials of these complexes. Fe(II) tetrakis-N,N,N',N'-(4-methoxy-2-pyridylmethyl)ethylenediamine (Fe(II)(4MeO)4TPEN) had the highest SOD activity (IC50=0.1 μM) among these iron-based SOD mimics. In addition, a good correlation was found between the redox potential and the SOD activity of 15 Fe(II) complexes, including iron-based SOD mimics reported in the previous paper (J. Organometal. Chem., in press). Iron-based SOD mimics may be clinically applicable, because these complexes are generally tissue-permeable and show low toxicity. Therefore our findings should be significant for the development of clinically useful SOD mimics.

INHIBITORS OF FARNESYL-PROTEIN TRANSFERASE

The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras

3(2H)-furanone derivatives

The present invention relates to 3(2H)-furanone compounds possessing fungicidal activity to plant fungi and a process for preparing them.

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.

2--1H-thienoimidazoles. A Novel Class of Gastric H+/K+-ATPase Inhibitors

2-thienoimidazoles were synthesized and investigated as potential inhibitors of gastric H+/K+-ATPase.The isomers of the two possible thienoimidazole series were found to be potent inhibitors of gastric acid secretion in vitro and in vivo.Structure-activity relationships indicate that especially lipophilic alkoxy, benzyloxy, and phenoxy substituents with additional electron-demanding properties in the 4-position of the pyridine moiety combined with an unsubstituted thienoimidazole lead to highly active compounds with a favorable chemical stability.Various substitution patterns in the thienoimidazole moiety result in lower biological activity.The heptafluorobutyloxy derivative saviprazole (HOE 731, 5d) was selected for further development and is currently undergoing clinical evaluation.Comprehensive pharmacological studies indicate a pharmacodynamic profile different to omeprazole, the first H+/K+-ATPase blocker introduced on the market.

4(3H)-quinazolinone derivatives and pharmaceutical compositions

4(3H)-Quinazolinone derivatives of formula (I) are provided. STR1 wherein R1 is a hydrogen atom, a C1 -C6 alkyl group, an aryl group, a substituted aryl group, or an aralkyl group; R2 is a C1 -C6 alkylamino group, a phenyl group, a substituted phenyl group, or a 5- or 6-membered heterocyclic group containing one or more N, O or S as a hetero atom or atoms, said heterocyclic group optionally being substituted or fused with a benzene ring; n is 1 or 2; or R2 represents a geranyl group or a dipyridylmethyl group together with the group --(CH2)n --; and X is a hydrogen atom, a C1 -C6 alkyl group or a halogen atom, and pharmaceutically acceptable acid addition salts thereof. They are useful as antiulcer agents.

Studies on 1,3-Benzoxazines. II. New Rearrangement Modes in the Reaction of 4-Chloro-2,2-dimethyl-2H-1,3-benzoxazine with Substituted Pyridine N-Oxides

New rearrangement modes in the reaction of 4-chloro-2,2-dimethyl-2H-1,3-benzoxazine (1) with various α- and/or γ-substituted pyridine N-oxides are described.The benzoxazine moiety was introduced into the side chain and/or β-position of the pyridine ring, in addition to the α-position.Possible mechanism of the reactions are discussed.Keywords - 1,3-benzoxazine; picoline N-oxide; lutidine N-oxide; imidoyl chloride; rearrangement.