63071-10-3

Usage

Uses

Used in Pharmaceutical Industry:
(4-CHLORO-PYRIDIN-2-YL)-METHANOL is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a key component in the development of new drugs targeting specific biological pathways.
Used in Inactivation of DDAH:
(4-CHLORO-PYRIDIN-2-YL)-METHANOL is used as an inactivator for dimethylarginine dimethylaminohydrolase (DDAH), an enzyme that plays a role in the regulation of nitric oxide production in the body. By inactivating DDAH, (4-CHLORO-PYRIDIN-2-YL)-METHANOL may have potential applications in the treatment of conditions related to nitric oxide dysregulation, such as cardiovascular diseases and certain neurological disorders.

Synthesis Reference(s)

Synthetic Communications, 19, p. 317, 1989 DOI: 10.1080/00397918908050984

InChI:InChI=1/C6H6ClNO/c7-5-1-2-8-6(3-5)4-9/h1-3,9H,4H2

Upstream product

• 856850-18-5 2-(bromomethyl)-4-chloropyridine 
• 696-08-2 4-chloro-2-picoline-N-oxide 
• 108-24-7 acetic anhydride 
• 67-56-1 methanol 
• 1121-76-2 4-chloropyridine N-oxide 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 24484-93-3 4-Chloro-pyridine-2-carboxylic acid methyl ester 
• 63071-06-7 (4-chloropyridin-2-yl)methyl acetate 
• 53750-66-6 4-chloro-pyridine-2-carbonyl chloride 
• 63071-13-6 4-chloro-2-pyridinecarbaldehyde 
• 7379-35-3 4-chlorpyridine hydrochloride 
• 98-98-6 2-Picolinic acid 
• 3678-63-5 4-chIoro-2-methylpyridine 
• 5470-66-6 2-methyl-4-nitropyridine N-oxide 

Downstream Products

• 119396-04-2 4-chloro-2-(chloromethyl)pyridine hydrochloride 
• 59886-58-7 N,N-dimethyl-4-aminopyridin-2-carbaldehyde 
• 500716-28-9 2-(aminomethyl)-4-(dimethylamino)pyridine 
• 99651-28-2 2-chloromethyl-4-methoxypyridine 
• 856850-18-5 2-(bromomethyl)-4-chloropyridine 
• 19235-89-3 4-chloro-pyridine-2-carbonitrile 
• 22282-65-1 4-iodo-2-methyl-pyridine 

Relevant academic research and scientific papers

DINUCLEATING LIGAND OR DINUCLEAR METAL COMPLEX

To provide a dinuclear metal complex that can be synthesized simply and easily and has a proper anticancer action.SOLUTION: The present disclosure provides a dinucleating ligand represented by the following formula (I) and a dinuclear metal complex thereof (where each X may be the same or different to represent H, Cl, OMe, or, Me, Y is H, a phenyl group, a substituted carbamoyl group or the like).SELECTED DRAWING: None

The Stronger the Better: Donor Substituents Push Catalytic Activity of Molecular Chromium Olefin Polymerization Catalysts

The donor strength of bifunctional pyridine-cyclopentadienyl ligands was altered systematically by the introduction of donating groups in the para-position of the pyridine. In the resulting chromium complexes an almost linear correlation between donor str

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.

Multiple Sulfonation of Picolyl-Based Complexes Rendering Them Highly Water-Compatible

Multidentate ligands chosen for the complexation of hard metals frequently exhibit negative charges, which consequently elicits Coulombic compensation of the metal-ion charge. However, ligands favored by soft metal ions are neutral, which prevents the chemist from obtaining electroneutral complexes, let alone ones with a negative total charge. Here, we report on an efficient synthetic method to decorate picolyl-displaying coordination compounds with multiple sulfonate units at their periphery. We further describe rare anionic versions of three standard complexes that have only been characterized as cationic so far. Our sulfonated complexes show extensive water solubility, which confers these species with great potential for broad application in the biomedical arena.

Homogeneous Hydrogenation with a Cobalt/Tetraphosphine Catalyst: A Superior Hydride Donor for Polar Double Bonds and N-Heteroarenes

The development of catalysts based on earth abundant metals in place of noble metals is becoming a central topic of catalysis. We herein report a cobalt/tetraphosphine complex-catalyzed homogeneous hydrogenation of polar unsaturated compounds using an air- and moisture-stable and scalable precatalyst. By activation with potassium hydroxide, this cobalt system shows both high efficiency (up to 24 000 TON and 12 000 h-1 TOF) and excellent chemoselectivities with various aldehydes, ketones, imines, and even N-heteroarenes. The preference for 1,2-reduction over 1,4-reduction makes this method an efficient way to prepare allylic alcohols and amines. Meanwhile, efficient hydrogenation of the challenging N-heteroarenes is also furnished with excellent functional group tolerance. Mechanistic studies and control experiments demonstrated that a CoIH complex functions as a strong hydride donor in the catalytic cycle. Each cobalt intermediate on the catalytic cycle was characterized, and a plausible outer-sphere mechanism was proposed. Noteworthy, external inorganic base plays multiple roles in this reaction and functions in almost every step of the catalytic cycle.

Synthesis method of 2-pyridylaldehyde derivative

The invention relates to the field of medical intermediates, in particular to a synthesis method of 2-pyridylaldehyde derivative. A synthesis path shown in the formula 1 is adopted, wherein X can be Cl or Br or CF3. Cheap starting raw materials are adopted, the use of hazardous materials which have large toxicity and are easily explosive is avoided, the cost of the product is greatly lowered, popularization and industrialized production are facilitated, and the synthesis method has the advantages of being low in cost, easy to operate, high in yield, easy to industrialize and the like. The formula 1 is shown in the description.

Chromatin Regulates Genome Targeting with Cisplatin

Cisplatin derivatives can form various types of DNA lesions (DNA-Pt) and trigger pleiotropic DNA damage responses. Here, we report a strategy to visualize DNA-Pt with high resolution, taking advantage of a novel azide-containing derivative of cisplatin we named APPA, a cellular pre-extraction protocol and the labeling of DNA-Pt by means of click chemistry in cells. Our investigation revealed that pretreating cells with the histone deacetylase (HDAC) inhibitor SAHA led to detectable clusters of DNA-Pt that colocalized with the ubiquitin ligase RAD18 and the replication protein PCNA. Consistent with activation of translesion synthesis (TLS) under these conditions, SAHA and cisplatin cotreatment promoted focal accumulation of the low-fidelity polymerase Polη that also colocalized with PCNA. Remarkably, these cotreatments synergistically triggered mono-ubiquitination of PCNA and apoptosis in a RAD18-dependent manner. Our data provide evidence for a role of chromatin in regulating genome targeting with cisplatin derivatives and associated cellular responses.

VISUAL DETECTION OF PLATINATED DNA LESIONS FROM A CLICKABLE CISPLATIN PROBE USED AS DIAGNOSTIC TOOL OR TO IDENTIFY SYNERGISTIC TREATMENTS

The present invention relates to a new compound for visualizing DNA-platinum crosslink, and its use as a research tool and in screening method for identifying candidate drug to be used in combination with platinating compounds such as cisplatin, carboplatin, and oxaliplatin. Formulae (I), (II) or (III). The project leading to this application has received funding from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation program (grant agreement No [647973]).

NOVEL MORPHOLINE DERIVATIVE OR SALT THEREOF

There is provided a morpholine derivative represented by General Formula [1A] or a salt thereof. (In the formula, a ring A represents a ring represented by General Formula [I]; * represents a bonding position; Z2 represents CH or the like; Z1 represents CR6 or the like; R6 represents a hydrogen atom or the like; X1 represents CHR7 or the like; R7 represents a hydrogen atom or the like; X2 represents CH2 or the like; R1 and R2 are the same as or different from each other, and each of R1 and R2 represents a hydrogen atom or the like; R3, R4, and R5 are the same as or different from each other, and each of R3, R4, and R5 represents a hydrogen atom, NRaRb, or the like; and each of Ra and Rb represents a hydrogen atom, a C1-8 alkyl group which may have a substituent, or the like.)

Design of coordination interaction of Zn(II) complex with oligo-aspartate peptide to afford a high-affinity tag-probe pair

A complementary recognition pair consisting of a genetically encodable peptide tag and a small molecular probe isa powerful tool to specifically label and manipulate a protein ofinterest under biological conditions. In this study, we report the redesign of a tag-probe pair comprising an oligo-aspartate peptide tag (such as DDDD) and a binuclear zinc complex. Isothermal-titration calorimetry screening of binding between the series of peptides and zinc complexes revealed that the binding affinity was largely influenced by subtle changes of the ligand structure of the probe. However, the binding was tolerant to differences of the tag peptide sequence. Of those tested, a pair containing a peptide tag (DDAADD) and a binuclear zinc complex possessing 4-chloropyridines (3-2Zn(II)) showed the strongest binding affinity (Ka = 3.88 × 105 M-1), which was about 10-fold larger than the conventional pair of D4-peptide tag (DDDD) and 1-2Zn(II) containing nonsubstituted pyridines (Ka = 3.73 × 104 M-1). The strong binding of this new complementary recognition pair enabled the rapid covalent labeling of a tag-fused maltose binding protein with a fluorescent zinc complex, demonstrating its potential utility in protein analysis.