202932-05-6

Basic information

• Product Name: 2-Pyridinemethanol,3,5-dimethyl-(9CI)
• Synonyms: 2-Pyridinemethanol,3,5-dimethyl-(9CI);2-HYDROXYMETHYL-3,5-DIMETHYLPYRIDINE;(3,5-diMethylpyridin-2-yl)Methanol;3,5-DiMethyl-2-pyridineMethanol
• CAS NO: 202932-05-6
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• Product Categories: PYRIDINE
• Mol File: 202932-05-6.mol

Chemical Properties

• Melting Point: 92 °C
• Boiling Point: 257.3±35.0 °C(Predicted)
• Appearance: /
• Density: 1.063±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.53±0.10(Predicted)
• CAS DataBase Reference: 2-Pyridinemethanol,3,5-dimethyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyridinemethanol,3,5-dimethyl-(9CI)(202932-05-6)
• EPA Substance Registry System: 2-Pyridinemethanol,3,5-dimethyl-(9CI)(202932-05-6)

Safety Data

• Hazardous Substances Data: 202932-05-6(Hazardous Substances Data)

Usage

Chemical Properties

Brown Oil

Uses

Intermediate in the preparation of Omeprazole metabolites

Upstream product

• 206990-64-9 acetic acid 3,5-dimethylpyridin-2-ylmethyl ester 
• 695-98-7 2,3,5-trimethyl-pyridine 
• 74409-42-0 2,3,5-trimethylpyridine 1-oxide 
• 67-56-1 methanol 

Downstream Products

• 153476-69-8 2-(chloromethyl)-3,5-dimethylpyridine 
• 73590-93-9 2-chloromethyl-3,5-dimethylpyridine hydrochloride 
• 170289-36-8 2-bromomethyl-3,5-dimethylpyridine 
• 1301167-88-3 2-[4-[1-(2-fluoroethyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]phenoxymethyl]-3,5-dimethylpyridine succinic acid 
• 1301167-87-2 2-[4-[1-(2-fluoroethyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]phenoxymethyl]-3,5-dimethylpyridine 
• 1301167-76-9 {5-[4-(3,5-dimethylpyridin-2-ylmethoxy)-phenyl]-4-pyridin-4-yl-pyrazol-1-yl}-acetic acid methyl ester 
• 1301167-75-8 C₂₅H₂₄N₄O₃ 
• 1320293-04-6 4-(3,5-dimethylpyridin-2-ylmethoxy)-N-methoxy-N-methylbenzamide 
• 1320293-07-9 1-[4-(3,5-dimethylpyridin-2-yl)methoxyphenyl]-2-pyridin-4-ylethanone 
• 1320293-08-0 3,5-dimethyl-2-[4-(4-(pyridin-4-yl)-2H-pyrazol-3-yl)phenoxymethyl]pyridine 
• 1301167-89-4 2-[4-[1-(2-⁽¹⁸⁾F-fluoroethyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]phenoxymethyl]-3,5-dimethylpyridine 
• 1320293-09-1 C₂₄H₂₃⁽¹⁸⁾FN₄O 
• 1320293-30-8 2-[5-[4-(3,5-dimethyl-pyridin-2-ylmethoxy)phenyl]-4-pyridin-4-ylpyrazol-1-yl]ethanol 
• 1301167-77-0 2-[3-[4-(3,5-dimethylpyridin-2-yl)methoxy]phenyl-4-pyridin-4-ylpyrazol-1-yl]ethanol 

Relevant articles and documents

Synthesis and characterization of one impurity in esomeprazole, an antiulcerative drug

During drug synthesis, control of impurities is very important to get high-qualified drugs. A number of studies have devoted to synthesize the impurities and study the structures to support the method of purification. In this paper, we first synthesize one impurity in esomeprazole, rel-2-[[(3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-6-methoxy-1H-benzimidazole, with readily available raw materials, simple operation procedures and relatively mild reaction. Besides, we characterized its structure by MS, IR, 1H-NMR and HPLC analyses. The purity of target compound is as high as 99.58%, which can be used as the reference substance of the impurities of esomeprazole.

Photochemical C-H Silylation and Hydroxymethylation of Pyridines and Related Structures: Synthetic Scope and Mechanisms

Considering the synthetic relevance of heteroarenes in various areas ranging from organic synthesis to medicinal chemistry, developing practically simple methodologies to access functionalized heteroarenes is of a significant value. Described herein is an efficient approach for C-H silylation and hydroxymethylation of pyridines and related heterocycles by the combination of silanes or methanol with readily available N-methoxypyridinium ions with a low catalyst loading (2 mol %) under blue light irradiation. The synthetic importance of the developed reactions is demonstrated by the synthesis of biologically relevant compounds. Electron paramagnetic resonance spectroscopy, quantum yield measurements, and density-functional theory calculations allowed us to understand reaction mechanisms of both photocatalytic reactions.

A chemical chaperone-based drug candidate is effective in a mouse model of amyotrophic lateral sclerosis (ALS)

Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the selective death of motor neurons and skeletal muscle atrophy. The majority of ALS cases are acquired spontaneously, with inherited disease accounting for only 10 % of all cases. Recent studies provide compelling evidence that aggregates of misfolded proteins underlie both types of ALS. Small molecules such as artificial chaperones can prevent or even reverse the aggregation of proteins associated with various human diseases. However, their very high active concentration (micromolar range) severely limits their utility as drugs. We synthesized several ester and amide derivatives of chemical chaperones. The lead compound 14, 3-((5-((4,6-dimethylpyridin-2-yl)methoxy)-5-oxopentanoyl)oxy)-N,N-dimethylpropan-1-amine oxide shows, in the micromolar concentration range, both neuronal and astrocyte protective effects in vitro; at daily doses of 10 mg kg-1 14 improved the neurological functions and delayed body weight loss in ALS mice. Members of this new chemical chaperone derivative class are strong candidates for the development of new drugs for ALS patients.

Synthesis and characterization of metabolites and potential impurities of the antiulcerative drug tenatoprazole

Tenatoprazole (Ulsacare) is a recently developed antiulcerative drug used for the treatment of both erosive and nonerosive gastroesophageal reflux disease. During the bulk synthesis of tenatoprazole, we have observed four impurities (tenatoprazole N-oxide, tenatoprazole sulfone N-oxide, N-methyl tenatoprazole, and desmethoxy tenatoprazole) and two metabolites (tenatoprazole sulfide and tenatoprazole sulfone). The present work describes the synthesis and characterization of these impurities. Copyright Taylor & Francis Group, LLC.

Rationally designed high-affinity 2-amino-6-halopurine heat shock protein 90 inhibitors that exhibit potent antitumor activity

Heat shock protein 90 (Hsp90) is a molecular chaperone protein implicated in stabilizing the conformation and maintaining the function of many cell-signaling proteins. Many oncogenic proteins are more dependent on Hsp90 in maintaining their conformation, stability, and maturation than their normal counterparts. Furthermore, recent data show that Hsp90 exists in an activated form in malignant cells but in a latent inactive form in normal tissues, suggesting that inhibitors selective for the activated form could provide a high therapeutic index. Hence, Hsp90 is emerging as an exciting new target for the treatment of cancer. We now report on a novel series of 2-amino-6-halopurine Hsp90 inhibitors exemplified by 2-amino-6-chloro-9-(4-iodo-3,5-dimethylpyridin- 2-ylmethyl)purine (30). These highly potent inhibitors (IC50 of 30 = 0.009 μM in a HER-2 degradation assay) also display excellent antiproliferative activity against various tumor cell lines (IC50 of 30 = 0.03 μM in MCF7 cells). Moreover, this class of inhibitors shows higher affinity for the activated form of Hsp90 compared to our earlier 8-sulfanylpurine Hsp90 inhibitor series. When administered orally to mice, these compounds exhibited potent tumor growth inhibition (>80%) in an N87 xenograft model, similar to that observed with 17-allylamino-17- desmethoxygeldanamycin (17-AAG), which is a compound currently in phase I/II clinical trials.

BASIC AMINE COMPOUND AND USE THEREOF

Novel amine compounds which are represented by the following formula (1) and efficacious against diseases such as a viral infectious disease with HIV, rheumatism, and cancer metastasis; typically, A 1 and A 2 represent a hydrogen atom or a substitutable monocyclic or polycyclic heteroaromatic ring and W represents a substitutable benzene ring or any group represented by the following formula (10) or (11): where X represents O, CH 2 , C(=O), NR 11 , or CHR 35 and D represents a group represented by the following formula (6): where Q represents a single bond, NR 12 , or a group represented by the formula (13): and Y represents a group represented by the following formula (7) : where z represents a substitutable monocyclic or polycyclic aromatic ring; and B represents -NR 25 R 26 ; and R 1 to R 26 in the above formulae represent a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group.

NOVEL HETEROCYCLIC COMPOUNDS AS HSP90-INHIBITORS

Novel heterocyclic compounds are described and demonstrated to have utility as Heat Shock Protein 90 (HSP90) inhibiting agent. Method of synthesis and use of such compounds are also described.

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.