63071-09-0

Basic information

• Product Name: 2-HYDROXYMETHYL-3-METHYLPYRIDINE
• Synonyms: 2-HYDROXYMETHYL-3-METHYLPYRIDINE;(3-METHYLPYRIDINE-2-YL)METHANOL;3-METHYL-2-PYRIDINEMETHANOL;(3-methylpyridin-2-yl)methanol;2-Pyridinemethanol, 3-methyl-
• CAS NO: 63071-09-0
• Molecular Formula: C₇H₉NO
• Molecular Weight: 123.15
• Product Categories: pharmacetical
• Mol File: 63071-09-0.mol

Chemical Properties

• Melting Point: 102 °C
• Boiling Point: 236.8 °C at 760 mmHg
• Flash Point: 97 °C
• Appearance: /
• Density: 1.092 g/cm³
• Vapor Pressure: 0.0255mmHg at 25°C
• Refractive Index: 1.544
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly, Sonicated)
• PKA: 13.51±0.10(Predicted)
• CAS DataBase Reference: 2-HYDROXYMETHYL-3-METHYLPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXYMETHYL-3-METHYLPYRIDINE(63071-09-0)
• EPA Substance Registry System: 2-HYDROXYMETHYL-3-METHYLPYRIDINE(63071-09-0)

Safety Data

• Hazardous Substances Data: 63071-09-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-HYDROXYMETHYL-3-METHYLPYRIDINE is used as a therapeutic agent for selectively suppressing MLL rearranged leukemia cells. 2-HYDROXYMETHYL-3-METHYLPYRIDINE targets and disrupts the MLL-1-WDR5 protein-protein interaction, which is a critical pathway in the development and progression of certain types of leukemia. By inhibiting this interaction, 2-HYDROXYMETHYL-3-METHYLPYRIDINE can potentially offer a novel treatment strategy for patients with MLL rearranged leukemia.

InChI:InChI=1/C7H9NO/c1-6-3-2-4-8-7(6)5-9/h2-4,9H,5H2,1H3

Upstream product

• 52814-41-2 2-(acetoxymethyl)-3-methylpyridine 
• 583-61-9 2,3-Lutidine 
• 22710-07-2 2,3-dimethylpyridine 1-oxide 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 4377-43-9 2-chloromethyl-3-methyl-pyridine 
• 4370-22-3 2-chloromethyl 3-methyl pyridine hydrochloride 
• 101870-40-0 (E)-3-methylpicolinaldehyde oxime 
• 927911-32-8 3-(2-fluorobenzyloxy)-5-((3-methylpyridin-2-yl)methoxy)benzaldehyde 
• 260395-28-6 N-benzyl-N,N'N'-tris(3-methylpyridin-2-ylmethyl)ethylene-1,2-diamine 
• 55589-47-4 3-methylpyridine-2-carboxaldehyde 

Relevant articles and documents

Methyl Scanning and Revised Binding Mode of 2-Pralidoxime, an Antidote for Nerve Agent Poisoning

Organophosphorus nerve agents (OPNAs) inhibit acetylcholinesterase (AChE) and, despite the Chemical Weapons Convention arms control treaty, continue to represent a threat to both military personnel and civilians. 2-Pralidoxime (2-PAM) is currently the only therapeutic countermeasure approved by the United States Food and Drug Administration for treating OPNA poisoning. However, 2-PAM is not centrally active due to its hydrophilicity and resulting poor blood-brain barrier permeability; hence, these deficiencies warrant the development of more hydrophobic analogs. Specifically, gaps exist in previously published structure activity relationship (SAR) studies for 2-PAM, thereby making it difficult to rationally design novel analogs that are concomitantly more permeable and more efficacious. In this study, we methodically performed a methyl scan on the core pyridinium of 2-PAM to identify ring positions that could tolerate both additional steric bulk and hydrophobicity. Subsequently, SAR-guided molecular docking was used to rationalize hydropathically feasible binding modes for 2-PAM and the reported derivatives. Overall, the data presented herein provide new insights that may facilitate the rational design of more efficacious 2-PAM analogs.

Effect of substituent in pyridine-2-carbaldehydes on their heterocyclization to 1,2,4-triazines and 1,2,4-triazine 4-oxides

A series of substituted pyridine-2-carbaldehydes were brought into heterocyclization with isonitrosoacetophenone hydrazones, followed by aromatization by the action of oxidants or by dehydration in boiling acetic acid. As a result, substituted 3-(pyridin-2-yl)-1,2,4-triazines or 3-(pyridin-2-yl)-1,2,4-triazine 4-oxides were formed. 6-Formylpyridine-2-carbonitrile failed to undergo heterocyclization, 6-methylpyridine-2-carbaldehyde and methyl 6-formylpyridine-3-carboxylate can be converted to both 1,2,4-triazine and 1,2,4-triazine 4-oxide derivative, and only 1,2,4-triazine 4 oxides were obtained from 6-bromopyridine-2-carbaldehyde and 6-formyl-3-phenylpyridine-2-carbonitrile. Convenient procedures were proposed for the synthesis of some initial pyridinecarbaldehydes.

NEUROLOGICALLY-ACTIVE COMPOUNDS

Neurologically-active heterocyclic compounds comprising two fused 6-membered rings with nitrogen atoms at positions 1 and 3, a carboxy group at position 4,and a hydroxy group at position 8, with one ring being aromatic. Processes for the preparation of these compounds and their use as pharmaceutical or veterinary agents, in particular for the treatment of neurological conditions, and more specifically neurodegenerative conditions such as Alzheimer's disease.

AMINE COMPOUNDS AND USE THEREOF

It is intended to provide novel amine compounds which are efficacious against diseases such as infection with HIV virus, rheumatism and cancer metastasis. Namely, amine compounds represented by the following general formula (1):In a typical case, A1 and A2 represent each an optionally substituted monocyclic or polycyclic aromatic heterocycle; W represents cyclic C3-10 alkylene, an optionally substituted monocyclic or polycyclic aromatic heterocycle, a monocyclic or polycyclic aromatic ring or a partly saturated polycyclic aromatic ring; X represents O, CH2, C(=O) or NR11; and D is a group represented by the following general formula (4) or (6).-Q-Y-BIn the formula (6), Q represents a single bond, S, O or NR12; and Y is a group represented by the following general formula (7). z represents an optionally substituted monocyclic or polycyclic aromatic ring. In the formula (6), B represents NR25R26. In the above formulae, R1 to R26 each represents hydrogen, alkyl, alkenyl or alkynyl.

NOVEL NITROGENOUS COMPOUND AND USE THEREOF

A novel nitrogen-containing compound effective against diseases such as HIV viral infectious diseases, rheumatism, and cancerous metastasis. It is a nitrogen-containing compound represented by the following general formula (1). In the formula, A typically represents a group represented by the formula (2) (A1 is hydrogen or an optionally substituted, mono- or polycyclic, heteroaromatic or aromatic ring; G1 is a single bond or a hydrocarbon group represented by the following formula (3) wherein R1, R2, and R3 may be optionally substituted hydrocarbon groups); W is an optionally substituted hydrocarbon group or heterocyclic ring; x is -C(=O)NH-; y is -C(=O)-; and D1 is hydrogen atom, alkyl having a polycyclic aromatic ring, di (substituted alkyl)amine, or alicyclic amine.

Bleach and oxidation catalyst

A bleach and oxidation catalyst is provided comprising a catalytically active iron, manganese or copper complex including a specified pentadentate nitrogen-containing ligand. The metal complex can activate hydrogen peroxide or peroxyacids and provides favourable stain removal properties. In addition, a considerably improved stability of these metal complex compounds in alkaline aqueous environment has been obtained, in particular at the peroxy compound concentrations generally present in the fabric washing liquor.

Synthesis, rotamer orientation, and calcium channel modulation activities of alkyl and 2-phenethyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-(3- or 6-substituted-2-pyridyl)-5-pyridinecarboxylates

A group of racemic alkyl and 2-phenethyl 1,4-dihydro-2,6-dimethyl-3- nitro-4-(3- or 6-substituted-2-pyridyl)-5-pyridinecarboxylates (13a-q) was prepared using a modified Hantzsch reaction that involved the condensation of a 3- or 6-substituted-2-pyridinecarboxaldehyde (7a-j) with an alkyl or 2- phenethyl 3-aminocrotonate (11a-d) and nitroacetone (12). Nuclear Overhauser (NOE) studies indicated there is a significant rotamer fraction in solution where the pyridyl nitrogen is oriented above the 1,4-dihydropyridine ring, irrespective of whether a substituent is located at the 3- or 6-position. A potential H-bonding interaction between the pyridyl nitrogen free electron pair and the suitably positioned 1,4-dihydropyridine NH moiety may stablize this rotamer orientation. In vitro calcium channel antagonist and agonist activities were determined using guinea pig ileum longitudinal smooth muscle (GPILSM) and guinea pig left atrium (GPLA) assays, respectively. Compounds having an i-Pr ester substituent acted as dual cardioselective calcium channel agonists (GPLA)/smooth muscle-selective calcium channel antagonists (GPILSM), except for the C-4 3-nitro-2-pyridyl compound which exhibited an antagonist effect on both GPLA and GPILSM. In contrast, the compounds with a phenethyl ester group, which exhibited antagonist activity (IC50 = 10-5- 10-7 M range) on GPILSM, were devoid of cardiac agonist activity on GPLA. Structure-activity relationships showing the effect of a substituent (Me, CF3, C1, NO2, Ph) at the 3- or 6-position of a C-4 2-pyridyl moiety and a variety of ester substituents (Me, Et, i-Pr, PhCH2CH2-) upon calcium channel modulation are described. Compounds possessing a 3- or 6-substituted- 2-pyridyl moiety, in conjuction with an i-Pr ester substituent, are novel 1,4-dihydropyridine calcium channel modulators that offer a new drug design approach directed to the treatment of congestive heart failure and may also be useful as probes to study the structure-function relationships of calcium channels.

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.