21514-99-8

Usage

Uses

Used in Pharmaceutical Industry:
[6-(Hydroxymethyl)pyridin-3-yl]methanol is used as a chemical building block for the synthesis of various pharmaceuticals, leveraging its unique structure and reactivity to create complex molecules with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, [6-(Hydroxymethyl)pyridin-3-yl]methanol serves as a key component in the development of new agrochemicals, contributing to the creation of innovative products designed to enhance crop protection and yield.
Used in Organic Synthesis:
[6-(Hydroxymethyl)pyridin-3-yl]methanol is utilized as a reagent in organic synthesis, playing a crucial role in the construction of intricate organic molecules for a wide array of applications, from materials science to specialty chemicals.
Overall, [6-(Hydroxymethyl)pyridin-3-yl]methanol's versatility and value as a chemical building block make it an essential component in the development and synthesis of a diverse range of compounds across multiple industries.

Upstream product

• 5620-35-9 pyridine-2,5-dicarboxylic acid dichloride 
• 100-26-5 Pyridine-2,5-dicarboxylic acid 
• 881-86-7 dimethyl 2,5-pyridine dicarboxylate 
• 55273-56-8 2,5-bis-acetoxymethyl-pyridine 
• 5552-44-3 ethyl 2,5-pyridinedicarboxylate 

Downstream Products

• 40749-33-5 5-(hydroxymethyl)-2-pyrimidinecarboxaldehyde 
• 42239-18-9 2,5-bis(bromomethyl)pyridine 
• 37877-95-5 [2](1,4)benzeno[2](2,5)pyridinophane 
• 1375006-73-7 5-(azidomethyl)-2-((4-(4-nitrophenyl)-1H-1,2,3-triazol-1-yl)methyl)pyridine 
• 1375006-81-7 (1-((6-((4-(4-nitrophenyl)-1H-1,2,3-triazol-1-yl)methyl)pyridin-3-yl)methyl)-1H-1,2,3-triazol-4-yl)methanol 
• 1375006-82-8 (1-((5-((4-(4-nitrophenyl)-1H-1,2,3-triazol-1-yl)methyl)pyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methanol 
• 1375006-83-9 5-((4-butyl-1H-1,2,3-triazol-1-yl)methyl)-2-((4-(4-nitrophenyl)-1H-1,2,3-triazol-1-yl)methyl)pyridine 
• 1375006-84-0 5-((4-butyl-1H-1,2,3-triazol-1-yl)methyl)-2-((4-(p-tolyl)-1H-1,2,3-triazol-1-yl)methyl)pyridine 
• 86238-83-7 (E)-1-(2-carbethoxy-5-pyridyl)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)butadiene 
• 50501-35-4 5-(Hydroxymethyl)-2-pyridincarbonsaeure-ethylester 
• 39977-41-8 5-(hydroxymethyl)picolinic acid 

Relevant academic research and scientific papers

New Water-Soluble Copper(II) Complexes with Morpholine-Thiosemicarbazone Hybrids: Insights into the Anticancer and Antibacterial Mode of Action

Six morpholine-(iso)thiosemicarbazone hybrids HL1-HL6 and their Cu(II) complexes with good-to-moderate solubility and stability in water were synthesized and characterized. Cu(II) complexes [Cu(L1-6)Cl] (1-6) formed weak dimeric associates in the solid state, which did not remain intact in solution as evidenced by ESI-MS. The lead proligands and Cu(II) complexes displayed higher antiproliferative activity in cancer cells than triapine. In addition, complexes 2-5 were found to specifically inhibit the growth of Gram-positive bacteria Staphylococcus aureus with MIC50 values at 2-5 μg/mL. Insights into the processes controlling intracellular accumulation and mechanism of action were investigated for 2 and 5, including the role of ribonucleotide reductase (RNR) inhibition, endoplasmic reticulum stress induction, and regulation of other cancer signaling pathways. Their ability to moderately inhibit R2 RNR protein in the presence of dithiothreitol is likely related to Fe chelating properties of the proligands liberated upon reduction.

A new planar chiral bipyridine ligand

Combined methods of cyclophane and bipyridine synthesis open the way to the new planar-chiral 2,2'-bipyridine 1, whose CD spectrum is strongly dependent on metal salts. The absolute configuration of the chiral precursor 2 could be assigned by comparison of experimental and theoretical CD spectra. The usefulness of planar chirality in heterocyclic transition metal ligands is revealed in experiments towards stereoselective catalysis using 1.

Design, synthesis, and biological characterization of a new class of symmetrical polyamine-based small molecule CXCR4 antagonists

CXCR4, a well-studied coreceptor of human immunodeficiency virus type 1 (HIV-1) entry, recognizes its cognate ligand SDF-1α (also named CXCL12) which plays many important roles, including regulating immune cells, controlling hematopoietic stem cells, and directing cancer cells migration. These pleiotropic roles make CXCR4 an attractive target to mitigate human disorders. Here a new class of symmetrical polyamines was designed and synthesized as potential small molecule CXCR4 antagonists. Among them, a representative compound 21 (namely HF50731) showed strong CXCR4 binding affinity (mean IC50 = 19.8 nM) in the CXCR4 competitive binding assay. Furthermore, compound 21 significantly inhibited SDF-1α-induced calcium mobilization and cell migration, and blocked HIV-1 infection via antagonizing CXCR4 coreceptor function. The structure-activity relationship analysis, site-directed mutagenesis, and molecular docking were conducted to further elucidate the binding mode of compound 21, suggesting that compound 21 could primarily occupy the minor subpocket of CXCR4 and partially bind in the major subpocket by interacting with residues W94, D97, D171, and E288. Our studies provide not only new insights for the fragment-based design of small molecule CXCR4 antagonists for clinical applications, but also a new and effective molecular probe for CXCR4-targeting biological studies.

Development of Gene-Targeted Polypyridyl Triplex-Forming Oligonucleotide Hybrids

In the field of nucleic acid therapy there is major interest in the development of libraries of DNA-reactive small molecules which are tethered to vectors that recognize and bind specific genes. This approach mimics enzymatic gene editors, such as ZFNs, TALENs and CRISPR-Cas, but overcomes the limitations imposed by the delivery of a large protein endonuclease which is required for DNA cleavage. Here, we introduce a chemistry-based DNA-cleavage system comprising an artificial metallo-nuclease (AMN) that oxidatively cuts DNA, and a triplex-forming oligonucleotide (TFO) that sequence-specifically recognises duplex DNA. The AMN-TFO hybrids coordinate CuII ions to form chimeric catalytic complexes that are programmable – based on the TFO sequence employed – to bind and cut specific DNA sequences. Use of the alkyne-azide cycloaddition click reaction allows scalable and high-throughput generation of hybrid libraries that can be tuned for specific reactivity and gene-of-interest knockout. As a first approach, we demonstrate targeted cleavage of purine-rich sequences, optimisation of the hybrid system to enhance stability, and discrimination between target and off-target sequences. Our results highlight the potential of this approach where the cutting unit, which mimics the endonuclease cleavage machinery, is directly bound to a TFO guide by click chemistry.

BIS-BENZIMIDAZOLE COMPOUNDS AND METHODS OF USING SAME

Provided herein are compounds and methods for modulating abnormal repeat expansions of gene sequences. More particularly, provided are inhibitors of RNA and the uses of such inhibitors in regulating nucleotide repeat expansions, e.g., to treat Myotonic Dystrophy Type 1 (DM1 ), Myotonic Dystrophy Type 2 (DM2), Fuchs dystrophy, Huntington Disease, Amyotrophic Lateral Sclerosis, or Frontotemporal Dementia.

BIS-AMINES, COMPOSITIONS, AND USES RELATED TO CXCR4 INHIBITION

This disclosure relates bis-amine compounds disclosed herein and uses related to CXCR4 inhibition. In certain embodiments, the compounds have formula (I), salts, derivatives, and prodrugs thereof wherein, A is a bridging aryl or heterocyclyl and R1 and R2 are further disclosed herein. In certain embodiments, the disclosure contemplates pharmaceutical compositions comprising compounds disclosed herein. In certain embodiments, the disclosure relates to methods of treating or preventing CXCR4 related diseases or conditions by administering an effective amount of a compound disclosed herein to a subject in need thereof.

Synthesis and evaluation of 2,5 and 2,6 pyridine-based CXCR4 inhibitors

Targeting the interaction between G-Protein Coupled Receptor, CXCR4, and its natural ligand CXCL12 is a leading strategy to mitigate cancer metastasis and reduce inflammation. Several pyridine-based compounds modeled after known small molecule CXCR4 antagonists, AMD3100 and WZ811, were synthesized. Nine hit compounds were identified. These compounds showed lower binding concentrations than AMD3100 (1000?nM) and six of the nine compounds had an effective concentration (EC) less than or equal to WZ811 (10?nM). Two of the hit compounds (2g and 2w) inhibited invasion of metastatic cells at a higher rate than AMD3100 (62%). Compounds 2g and 2w also inhibit inflammation in the same range as WZ811 in the paw edema test at 40% reduction in inflammation. These preliminary results are the promising foundation of a new class of pyridine-based CXCR4 antagonists.

A Ca2+-, Mg2+-, and Zn2+-Based Dendritic Contractile Nanodevice with Two pH-Dependent Motional Functions

A contractile dendritic motional device is reported where metal ions with biological importance - Ca2+ (the main regulatory and signaling species of the natural muscles), Mg2+, and Zn2+ - initiate two kinds of motional functions. The first motional function is the metal-ion-induced contraction of a linear strand into a Z-shaped dinuclear complex, and the second one is the change of the height of Z-shaped complexes via transmetalation. By means of the pH-dependent counterligand tren, the two motional features of the machine can depend on alternate additions of acid and base. An optical response is associated with the conversion of the linear form (which is yellow) into the metalated Z-shaped one (which is red).

UMSYMMETRICAL BISAZIDES FOR CHEMOSELECTIVE SEQUENTIAL LIGATION

Unsymmetrical bisazides containing chelating and non-chelating azido groups undergo chemoselective three-component copper(I)-catalyzed azide-alkyne conjugation reactions with two different alkyne molecules. In conjunction with the reactivity gap between a

Synthesis of planar chiral N-heterocyclic-substituted pyridinophanes

Four new planar chiral N-heterocyclic-substituted [2](1,4)benzene[2](2,5) pyridinophanes have been synthesized. With the attached pyrazole, triazole, tetrazole, and pyrimidine moieties, different N,N-chelating ligands that vary in the number of enclosed nitrogen atoms, ring size, and electronic properties were added to a mostly neglected class of pyridinophanes. Additionally, the known synthesis of the pyridinophane scaffold was simplified considerably. With the acetyl, amino, and amido pyridinophane, various useful intermediates for new pyridinophane ligands were synthesized, which would allow for further investigations of this ligand system. New planar chiral bis(heterocyclic) N-donors based on the rarely investigated class of [2](1,4)-benzene[2](2,5) pyridinophanes were synthesized. The synthesis of the pyridinophane scaffold was simplified, and a pyrazole, triazole, tetrazole, and pyrimidine heterocycle were successfully attached to the planar chiral backbone. Copyright