2510-23-8

Usage

Chemical Properties

Colorless to brownish low melting solid

Synthesis Reference(s)

Tetrahedron, 62, p. 6673, 2006 DOI: 10.1016/j.tet.2005.12.077

InChI:InChI=1/C6H4N2/c1-2-6-4-3-5-7-8-6/h1,3-5H

Upstream product

• 63671-83-0 2-chloro-2-(3-pyridyl)ethene 
• 3246-80-8 9-phenyl-9H-xanthene 
• 80673-00-3 3-[(trimethylsilyl)ethynyl]pyridine 
• 24202-80-0 2-methyl-4-(pyridin-3-yl)but-3-yn-2-ol 
• 626-55-1 3-Bromopyridine 
• 4301-14-8 acetylenemagnesium bromide 
• 500-22-1 3-pyridinecarboxaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 67-56-1 methanol 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 145397-30-4 C₈H₂₁N₄PSi 
• 944418-72-8 3-[(1Z)-2-iodoethenyl]pyridine 
• 63671-82-9 3-(2,2-dibromovinyl)pyridine 
• 462-08-8 pyridin-3-ylamine 

Downstream Products

• 157195-63-6 6-Chloro-4-cyclopropyl-1-(4-methoxy-benzyl)-4-pyridin-3-ylethynyl-3,4-dihydro-1H-quinazolin-2-one 
• 120241-79-4 4-(3-pyridyl)-2H-1,2,3-triazole 
• 218431-38-0 1-bromo-2-(3-pyridyl)acetylene 
• 219480-92-9 3-(1-butynyl)pyridine 
• 219480-94-1 3-(1-pentyn-4-enyl)pyridine 
• 306973-76-2 (1S,2S,5R)-2-i-propyl-5-methyl-1-[2-(3-pyridinyl)-1-ethyn-1-yl]cyclohexan-1-ol 
• 500907-28-8 5'-O-(4,4'-dimethoxytrityl)-5-(pyridin-3-yl-ethynyl)-2'-deoxyuridine 
• 79476-36-1 3,5-Di(3-pyridyl)pyrazole 
• 114880-30-7 4-(pyridin-3-yl)but-3-yn-2-one 

Relevant academic research and scientific papers

Controlling hydrogen-bond preferences in bipyridines with competing binding sites

The design and synthesis of a family of supramolecular reagents (SRs) based on ethynyl-spaced substituted bipyridines are described, and their potential use as molecular 'hubs' for the predictable construction of binary and ternary co-crystals is explored. Each SR was synthesized in good yields through consecutive Pd-catalyzed Sonogashira cross-coupling reactions. Crystal structures of three binary co-crystals are presented with each structure clearly illustrating how accurate supramolecular assembly control can be achieved by increasing/decreasing the strength of the participating hydrogen-bond interactions.

Passive monitoring method for 3-Ethenylpyridine: A marker for environmental tobacco smoke

A new method was developed to assess environmental tobacco smoke in air. The method is based on passive sampling and subsequent measurement of the concentration of 3-ethenylpyridine, a vapor-phase compound specific to tobacco smoke. Air samples were collected using a 3M organic vapor monitor. Tests were carried out in a dynamic chamber to determine the sampling rate (25.7 cm3/ min). 3-Ethenylpyridine was desorbed from the sampler with 1 mL of pyridine/toluene mixture. 3-Ethenylpyridine was quantified by gas chromatography/mass spectrometry. The limit of detection was 0.01 μg/sample, corresponding to a concentration of 0.27 μg/m3 air calculated for a sampling period of 24 h. Field measurements were carried out to test the performance of the method. Mean concentrations ranging from 1.3 to 5.3μg/m3 were measured for 3-ethenylpyridine in smoking environments, but no 3-ethenylpyridine was detected in nonsmoking environments. Active sampling using charcoal tubes was used as a reference method in the chamber tests and field measurements. Individual exposures can be easily and accurately measured by means of the passive sampler. Because of simple sample treatment, the method is also well-suited for large-scale monitoring of environmental tobacco smoke.

Synthesis of 1-hetarylethylphosphonates

Previously unknown potentially biologically active diethyl 1-(pyridin-3-yl)-, 1-(quinolin-3-yl)-, and 1-(quinolin-6-yl)ethylphosphonates were synthesized by palladium-catalyzed reduction of the corresponding α,β-unsaturated precursors with ammonium formate. The reduction of diethyl 1-(quinolin-6-yl)ethenylphosphonate was accompanied by formation of diethyl 1-(1,2,3,4-tetrahydroquinolin-6-yl)ethylphosphonate as by-product.

Synthesis, Electrochemistry, and Optical Properties of Highly Conjugated Alkynyl-Ferrocenes and -Biferrocenes

Sonogashira reactions are utilized herein to react iodo-ferrocenes and -biferrocenes with terminal alkyne ligands, functionalized with both pyridine and thioanisole groups. High-yielding reactions generate both monoalkynyl and dialkynyl derivatives, the r

Synthesis and Photochemical Application of Hydrofluoroolefin (HFO) Based Fluoroalkyl Building Block

A novel fluoroalkyl iodide was synthesized on multigram scale from refrigerant gas HFO-1234yf as cheap industrial starting material in a simple, solvent-free, and easily scalable process. We demonstrated its applicability in a metal-free photocatalytic ATRA reaction to synthesize valuable fluoroalkylated vinyl iodides and proved the straightforward transformability of the products in cross-coupling chemistry to obtain conjugated systems.

Design and characterization of a heterocyclic electrophilic fragment library for the discovery of cysteine-targeted covalent inhibitors

A fragment library of electrophilic small heterocycles was characterized through cysteine-reactivity and aqueous stability tests that suggested their potential as covalent warheads. The analysis of theoretical and experimental descriptors revealed correlations between the electronic properties of the heterocyclic cores and their reactivity against GSH that are helpful in identifying suitable fragments for cysteines with specific nucleophilicity. The most important advantage of these fragments is that they show only minimal structural differences from non-electrophilic counterparts. Therefore, they could be used effectively in the design of targeted covalent inhibitors with minimal influence on key non-covalent interactions.

Na2S-mediated synthesis of terminal alkynes from: Gem -dibromoalkenes

The Na2S-mediated facile synthesis of terminal alkynes from gem-dibromoalkenes, at 20/40 °C under open flask conditions has been developed. Various precursors derived from heteroaromatic/aromatic/aliphatic aldehydes were found compatible. The reaction is proposed to proceed through the Fritsch-Buttenberg-Wiechell (FBW) rearrangement involving the corresponding vinyl carbene. Using mild reaction conditions with inexpensive Na2S·9H2O under air atmosphere has significant advantages over earlier routes.

Heterocyclic compound and organic light-emitting device including the same

A heterocyclic compound represented by Formula 1 below, and an organic light-emitting device including the heterocyclic compound:

Octahedral [Pd6L8]12+ Metallosupramolecular Cages: Synthesis, Structures and Guest-Encapsulation Studies

Four planar tripyridyl ligands (Ltripy), 1,3,5-tris(pyridin-3-ylethynyl)benzene 1 a, 1,3,5-tris[4-(3-pyridyl)phenyl]benzene 2 a, and the hexyloxy chain functionalized derivatives 1,3,5-tris[(3-hexyloxy-5-pyridyl)ethynyl]benzene 1 b, and 1,3,5-tris[4-(3-hexyloxy-5-pyridyl)phenyl]benzene 2 b, were synthesized and used to generate a family of [Pd6(Ltripy)8](BF4)12 octahedral cages (Ltripy=1 a, b or 2 a, b). The ligands and cages were characterized using a combination of 1H, 13C, and DOSY nuclear magnetic resonance (NMR) spectroscopy, high resolution electrospray mass spectrometry (HR-ESI-MS), infrared (IR) spectroscopy, elemental analysis, and in three cases, X-ray crystallography. The molecular recognition properties of the cages with neutral and anionic guests were examined, in dimethyl sulfoxide (DMSO), using NMR spectroscopy, mass spectrometry and molecular modeling. No binding was observed with simple aliphatic and aromatic guest molecules. However, anionic sulfonates were found to interact with the octahedral cages and the binding interaction was size selective. The smaller [Pd6(1 a, b)8]12+ cages were able to interact with three p-toluenesulfonate guest molecules while the larger [Pd6(2 a, b)8]12+ systems could host four of the anionic guest molecules. To probe the importance of the hydrophobic effect, a mixed water–DMSO (1:1) solvent system was used to reexamine the binding of the neutral organic guests adamantane, anthracene, pyrene and 1,8-naphthalimide within the cages. In this solvent system all the guests except adamantane were observed to bind within the cavities of the cages. NMR spectroscopy and molecular modeling indicated that the cages bind multiple copies of the individual guests (between 3–6 guest molecules per cage).

Small Molecule Inhibitors Simultaneously Targeting Cancer Metabolism and Epigenetics: Discovery of Novel Nicotinamide Phosphoribosyltransferase (NAMPT) and Histone Deacetylase (HDAC) Dual Inhibitors

Cancer metabolism and epigenetics are among the most intensely pursued research areas in anticancer drug discovery. Here we report the first small molecules that simultaneously inhibit nicotinamide phosphoribosyltransferase (NAMPT) and histone deacetylase (HDAC), two important targets of cancer metabolism and epigenetics, respectively. Through iterative structure-based drug design, chemical synthesis, and biological assays, a highly potent dual NAMPT and HDAC inhibitor was successfully identified. Compound 35 possessed excellent and balanced activities against both NAMPT (IC50 = 31 nM) and HDAC1 (IC50 = 55 nM). It could effectively induce cell apoptosis and autophagy and ultimately led to cell death. Importantly, compound 35 showed excellent in vivo antitumor efficacy in the HCT116 xenograft model. This proof-of-concept study demonstrates the feasibility of discovering an inhibitor targeting cancer metabolism and epigenetics and provides an efficient strategy for multitarget antitumor drug discovery.