263012-63-1

Usage

Uses

Used in Supramolecular Nanoengineering:
Pyridine, 2-chloro-5-ethynyl(9CI) is used as a key intermediate in the synthesis of conjugatively bridged bisand tris-5-(2,2'-bipyridines) multitopic metal ion-binding modules. These modules are essential components in supramolecular nanoengineering, which is a field that focuses on the design and construction of complex molecular structures and systems through non-covalent interactions.
In this application, the compound plays a crucial role in the development of advanced materials and devices with specific functions, such as molecular recognition, sensing, and self-assembly. The unique properties of Pyridine, 2-chloro-5-ethynyl(9CI) make it a valuable building block for creating novel structures with potential applications in various industries, including pharmaceuticals, materials science, and nanotechnology.

InChI:InChI=1/C7H4ClN/c1-2-6-3-4-7(8)9-5-6/h1,3-5H

Upstream product

• 53939-30-3 5-bromo-2-chloropyridine 
• 142-08-5 2-hydroxypyridin 
• 13472-79-2 5-iodo-pyridin-2-ol 
• 69045-79-0 2-choro-5-iodopyridine 
• 263012-81-3 2-chloro-5-[(trimethylsilyl)ethynyl]-2,2'-bipyridine 

Downstream Products

• 87148-60-5 2-chloro-5-(2-phenylethynyl)pyridine 
• 263012-62-0 1,2-bis(5-ethynyl-2-chloropyridyl)benzene 
• 349659-52-5 2-chloro-5-[(2-trimethylsilylethynylphenyl)ethynyl]pyridine 
• 349659-64-9 2-chloro-5-[(2-ethynylphenyl)ethynyl]pyridine 
• 349659-60-5 5,5'-bis[(2-ethynylphenyl)ethynyl]-2,2'-bipyridine 
• 349659-56-9 5,5'-bis[(2-trimethylsilylethynylphenyl)ethynyl]-2,2'-bipyridine 
• 865798-05-6 3-[4-(6-chloro-pyridin-3-yl)-1,2,3-triazol-1-yl]-4-methyl-benzoic acid 
• 728878-19-1 4-[4-(6-chloropyridin-3-yl)buta-1,3-diynyl]benzoic acid methyl ester 
• 1293385-68-8 5-ethynyl-2-(2-(4-(thiophen-2-yl)benzylidene)hydrazinyl)pyridine 
• 1293979-80-2 6-ethynyl-3,3-difluoro-2-(4-(thiophen-2-yl)benzylidene)-2,3-dihydro[1,2,4,3]triazaborolo[4,5-a]pyridin-2-ium-3-uide 
• 728878-18-0 4-[4-(6-chloropyridin-3-yl)buta-1,3-diynyl]benzoic acid 

Relevant academic research and scientific papers

PCSK9 INHIBITORS AND METHODS OF USE THEREOF

The invention relates to a novel inhibitor pharmacophore of PCSK9 and heteroaryl compounds that bind the PCSK9 protein.

PCSK9 INHIBITORS AND METHODS OF USE THEREOF

The invention relates to novel heteroaryl compounds and pharmaceutical preparations thereof. The invention further relates to methods of treating or preventing cardiovascular diseases, and methods treating sepsis or septic shock, using the novel heterocyclic compounds disclosed herein.

Modular, Concise, and Efficient Synthesis of Highly Functionalized 5-Fluoropyridazines by a [2 + 1]/[3 + 2]-Cycloaddition Sequence

An easy access to 5-fluoropyridazines by a [2 + 1]/[3 + 2]-cycloaddition sequence between terminal alkynes, a difluorocarbene, and a diazo compound is reported. This approach does not necessitate the isolation of any intermediates, and a wide range of novel 5-fluoropyridazines was synthesized from readily available starting materials. Additionally, these compounds were used as a platform to access novel and highly diversified pyridazines.

Synthesis and Structural Characterization of Ethynylene-Bridged Bisazines Featuring Various α-Substitution

A series of bispyridines and bispyrimidines 1a, 1b, 1c, 1d, 1e showing the heterocycles attached to both ends of an ethynylene unit and being α-substituted with chloro, tert-butylthio, and methoxy groups have been synthesized via cross-coupling technique and their crystal structures studied by X-ray diffraction analysis. Supramolecular interactions of C-H···N and π···π stacking type were found to largely dominate the structures according to the compound species. A trial was given to deduce the markedly differing temperatures of melting among the compounds from special features of the crystal structures.

Design and synthesis of a new class of membrane-permeable triazaborolopyridinium fluorescent probes

A new class of fluorescent triazaborolopyridinium compounds was synthesized from hydrazones of 2-hydrazinylpyridine (HPY) and evaluated as potential dyes for live-cell imaging applications. The HPY dyes are small, their absorption/emission properties are

3-‘4-HETEROCYCLYL -1,2,3,-TRIAZOL-1-YL!-N-ARYL-BENZAMIDES AS INHIBITORS OF THE CYTOKINES PRODUCTION FOR THE TREATMENT OF CHRONIC INFLAMMATORY DISEASES

Disclosed compounds of formula (I), which inhibit production of cytokines involved in inflammatory processes and are thus useful for treating diseases and pathological conditions involving inflammation such as chronic inflammatory disease. Also disclosed are processes for preparing these compounds and pharmaceutical compositions comprising these compounds.

Synthesis and properties of a twistophane ion sensor: A new conjugated macrocyclic ligand for the spectroscopic detection of metal ions

The synthesis of a structurally new type of conjugated macrocyclic ligand (1) is reported that comprises a dehydroannulene framework incorporating two 2,2′-bipyridine units. Modeling studies showed the ligand to possess an unusual chirally twisted and relatively rigid architecture capable of binding metal ions in an enforced tetrahedral coordination geometry. The macrocycle was prepared in seven steps from (2-bromophenylethynyl)-trimethylsilane (2) and characterized by spectroscopic techniques. The pyridine H3 protons in the 1H NMR spectrum of 1 showed a marked temperature dependencey that may be related to conformational opening and closing motions of the macrocyclic ring. Ligand 1 was found to spectroscopically detect the presence of Co2+, Ni2+, Cu2+, and Zn2+ and, in particular, to function as a multiple readout sensor, giving different sequences of signal output depending upon the type of metal ion analyte with which the system was addressed. Macrocycle 1 also gave a highly characteristic and specific visual output response in the presence of Zn2+ consisting of a bright turquoise fluorescence and in this respect may find applications in the sensing of this biologically important metal ion.

A Synthesis of Conjugatively Bridged Bis- and Tris-5-(2,2′-Bipyridines): Multitopic Metal Ion-Binding Modules for Supramolecular Nanoengineering

An efficient preparation of linear and curved bis- and branched tris-5-(2,2′-bipyridines) of nanoscopic dimensions possessing rigid conjugated bridges is presented. The synthesis, which avoids the need of protection/deprotection methodology, utilizes central bridge precursors which are outwardly diand trifunctionalized with a 5-(2-chloropyridine) synthon via a chemoselective palladium-catalyzed Sonogashira or Negishi cross-coupling protocol to yield the bridged linear (5a-c, 5f,g) and curved (6, 7) bis- and branched (8) tris-5-(2-chloropyridines). Under more forcing conditions, the ethynebridged 5-(2-chloropyridines) undergo the Stille cross-coupling reacton with 2-trimethylstannylpyridines to afford the conjugatively bridged linear (1a,b, 1g-j) and curved (2a,b, 3a,b) bis- and branched, (4a,b) tris-5-(2,2′-bipyridines) in good overall yields. The phenyl- and biphenyl-bridged linear bis-5-(2,2′-bipyridines) (1c-f) were best prepared from the bis-5-(2-bromopyridines) (5d,e) to ensure completion of the Stille cross-coupling reactions. The Stille cross-couplings showed a marked substituent effect in which the terminally phenylated bis- and tris-5-(2,2′-bipyridines) were formed in higher yields than the methyl-substituted analogues with the same bridge. The advantages of the methodology lie in its synthetic convenience and adaptibility for creating multitopic metal ion-binding scaffolds with a potentially very large variety of bridging units and substituents on the terminal pyridine rings. The bridged 5-(2-chloropyridines) may also serve as precursors for the fabrication of metal ion-coordinated conjugated polymers.