58792-53-3

Usage

Uses

Used in Coordination Chemistry:
[2,2'-Bipyridine]-5-carboxylic acid, methyl ester is used as a ligand for its ability to coordinate with transition metal ions, which is crucial in the development of new coordination compounds with specific properties.
Used in Catalysis:
[2,2'-Bipyridine]-5-carboxylic acid, methyl ester serves as a catalyst or a catalyst precursor in various chemical reactions, leveraging its coordination capabilities to enhance reaction rates and selectivity.
Used in Organic Synthesis:
[2,2'-Bipyridine]-5-carboxylic acid, methyl ester is utilized as a building block or intermediate in the synthesis of more complex organic molecules, contributing to the diversity of organic chemistry.
Used in Material Science:
It is employed in the development of new materials, such as sensors, polymers, or other functional materials, due to its unique structural and chemical features.
Used in Pharmaceutical Industry:
[2,2'-Bipyridine]-5-carboxylic acid, methyl ester has potential uses in the pharmaceutical sector, possibly as a precursor to drugs or in the development of active pharmaceutical ingredients, owing to its versatile chemical properties.
Used in Agrochemical Industry:
[2,2'-Bipyridine]-5-carboxylic acid, methyl ester may also find applications in agrochemicals, potentially as a component in the synthesis of pesticides or other agrochemical products, given its reactivity and coordination capabilities.

Upstream product

• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 73781-91-6 6-Chloronicotinic acid methyl ester 
• 13737-05-8 2-trimethylstannylpyridine 
• 140447-00-3 2,2'-bipyridine-5-carbonyl chloride 
• 109-04-6 2-bromo-pyridine 
• 56100-20-0 5-methyl-2,2'-bipyridine 
• 1970-80-5 2,2'-bipyridine-5-carboxylic acid 
• 17997-47-6 2-tri-n-butylstannylpyridine 

Downstream Products

• 1427462-45-0 5-(-N-(p-O-(N'-acetyl-(β-D-glucosaminyl)phenyl)aminocarbonyl))-2,2'-bipyridine 
• 1427462-44-9 5-(-N-(p-O-(β-D-galactosyl)phenyl)-aminocarbonyl)-2,2'-bipyridine 
• 1427462-43-8 5-(-N-(p-O-(β-D-glucosyl)phenyl)-aminocarbonyl)-2,2'-bipyridine 
• 1427462-42-7 5-(-N-(p-O-(β-lactosyl)phenyl)aminocarbonyl)-2,2'-bipyridine 
• 1427462-41-6 5-(-N-(p-O-(3,4,6-tri-O-acetyl-N'-acetyl-β-D-glucosaminyl)phenyl)aminocarbonyl)-2,2'-bipyridine 
• 1427462-40-5 5-(-N-(p-O-(2,3,4,6-tetra-O-acetyl-β-D-galactosyl)phenyl)-aminocarbonyl)-2,2'-bipyridine 
• 1427462-39-2 5-(-N-(p-O-(2,3,4,6-tetra-O-acetyl-β-D-glucosyl)phenyl)aminocarbonyl)-2,2'-bipyridine 
• 1427462-38-1 5-(-N-(p-O-(2,3,6,2,3,4,6-Hepta-O-acetyl-β-lactosyl)phenyl)-aminocarbonyl)-2,2'-bipyridine 
• 220339-96-8 5-(aminomethyl)-2,2′-bipyridine 

Relevant academic research and scientific papers

Affinity-Enhanced Luminescent Re(I)- and Ru(II)-Based Inhibitors of the Cysteine Protease Cathepsin L

Two new Re(I)- and Ru(II)-based inhibitors were synthesized with the formulas [Re(phen)(CO)3(1)](OTf) (7; phen = 1,10-phenanthroline, OTf = trifluoromethanesulfonate) and [Ru(bpy)2(2)](Cl)2 (8; bpy = 2,2′-bipyridine), where 1 and 2 are the analogues of CLIK-148, an epoxysuccinyl-based cysteine cathepsin L inhibitor (CTSL). Compounds 7 and 8 were characterized using various spectroscopic techniques and elemental analysis; 7 and 8 both show exceptionally long excited state lifetimes. Re(I)-based complex 7 inhibits CTSL in the low nanomolar range, affording a greater than 16-fold enhancement of potency relative to the free inhibitor 1 with a second-order rate constant of 211000 ± 42000 M-1 s-1. Irreversible ligation of 7 to papain, a model of CTSL, was analyzed with mass spectroscopy, and the major peak shown at 24283 au corresponds to that of papain-1-Re(CO)3(phen). Compound 7 was well tolerated by DU-145 prostate cancer cells, with toxicity evident only at high concentrations. Treatment of DU-145 cells with 7 followed by imaging via confocal microscopy showed substantial intracellular fluorescence that can be blocked by the known CTSL inhibitor CLIK-148, consistent with the ability of 7 to label CTSL in living cells. Overall this study reveals that a Re(I) complex can be attached to an enzyme inhibitor and enhance potency and selectivity for a medicinally important target, while at the same time allowing new avenues for tracking and quantification due to long excited state lifetimes and non-native element composition.

The isolation and purification of tris-2,2′-bipyridine complexes of ruthenium(II) containing unsymmetrical ligands

Monomeric ruthenium(II) complexes [Ru(L)3]2+ containing unsymmetric bipyridine ligands [Where L = 5-methyl-2,2′-bipyridine (L1), 5-ethyl-2,2′-bipyridine (L2), 5-propyl-2,2′-bipyridine (L3), 5-(2-methylpropyl)-2,2′-bipyridine (L4), 5-(2,2-dimethylpropyl)-2,2′-bipyridine (L5) or 5-(carbomethoxy)-2,2′-bipyridine (L6)] have been studied and the meridional and facial isomers isolated by the use of cation-exchange column chromatography (SP Sephadex C-25) eluting with either sodium toluene-4-sulfonate or sodium hexanoate. The relative yield of the facial isomer was found to decrease with increasing steric bulk, preventing the isolation of fac-[Ru(L5)3]2+. The two isomeric forms were characterized by 1H NMR spectroscopy, with the complexes [Ru(L1-3)3]2+ demonstrating an unusually large coupling between the H6 and H4 protons. Crystals suitable for X-ray structural analysis of [Ru(L1)3]2+ were obtained as a mixture of the meridional and facial isomers, indicating that separation of this isomeric mixture could not be achieved by fractional crystallisation. The optical isomers of the complex [Ru(L3)3]2+ were chromatographically separated on SP Sephadex C-25 relying upon the inherent chirality of the support. It is apparent that chiral interactions can inhibit geometric isomer separation using this technique.

Use of a Compact Tripodal Tris(bipyridine) Ligand to Stabilize a Single-Metal-Centered Chirality: Stereoselective Coordination of Iron(II) and Ruthenium(II) on a Semirigid Hexapeptide Macrocycle

Fe(II)-coordinating hexapeptides containing three 2,2′-bipyridine moieties as side chains were designed and synthesized. A cyclic hexapeptide having three [(2,2′-bipyridin)-5-yl]-d-alanine (d-Bpa5) residues, in which d-Bpa5 and Gly are alternately arranged with 3-fold rotational symmetry, coordinated with Fe(II) to form a 1:1 octahedral Fe(II)-peptide complex with a single facial-? configuration of the metal-centered chirality. NMR spectroscopy and molecular dynamics simulations revealed that the Fe(II)-peptide complex has an apparent C3-symmetric conformations on the NMR time scale, while the peptide backbone is subject to dynamic conformational exchange between three asymmetric β/γ conformations and one C3-symmetric γ/γ/γ conformation. The semirigid cyclic hexapeptide preferentially arranged these conformations of the small octahedral Fe(II)-bipyridine complex, as well as the Ru(II) congener, to underpin the single configuration of the metal-centered chirality.

[...] derivative comprising a fluorescent compound

PROBLEM TO BE SOLVED: To provide a novel fluorescent compound applicable to detection and measurement of various biological materials.SOLUTION: A fluorescent compound is provided which is represented by formula (I), where X and Y each represent independen

DIPYRIDINIUM DERIVATIVES

Compounds of Formula (I): α-x-β (I) and pharmaceutically acceptable salts and solvates thereof, wherein α, x, and β have the meanings as indicated in the specification, are useful for treating a disease or disorder characterised by pathologically proliferating cells, particularly cancer. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.

Glycosylated tris-bipyridine ferrous complexes to provide dynamic combinatorial libraries for probing carbohydrate-carbohydrate interactions

2,2-Bipyridines having β-lactoside, β-d-glucoside, β-d-galactoside, and N-acetyl-β-d-glucosaminide were prepared and then, complexed with ferrous ion to afford trivalent glycoclusters having tris-bipyridine ferrous complex cores. Each glycocluster provides a dynamic combinatorial library composed of four diastereomeric stereoisomers (Δmer, Δfac, Λmer, and Λfac) whose ratios depend on their relative stabilities. CD spectral analyses of these glycoclusters showed that various cations (Na+, Mg2+, K+ or Ca2+) enriched Δ-forms of the glycocluster having β-lactosides and N-acetyl-β-d-glucosaminides possibly by cations-induced intramolecular carbohydrate-carbohydrate interactions.

Electrochemiluminescent dinuclear Ru(II) complexes assembled with 1,1′-(1,2-ethynediyl)- or dimethlyene-bridged bis(bipyridine) ligands: Synthesis and photophysical and electrochemical properties

1,2-Di(2,2′-bipyridin-5-yl)ethane (BL1) and 1,2-di(2,2′- bipyridin-5-yl)ethyne (BL2) were synthesized as new bridging ligands and coordinated to (RuL2(acetone)2)(PF6) 2 for the preparation of various [Ru(L)2(BL)Ru(L) 2](PF6)4-type dinuclear ruthenium complexes (where BL = BL1, BL2 and L = bpy, o-phen, DTDP). The electrochemical redox potentials, spectroscopic properties, and relative electrochemiluminescence intensity of BL1 and BL2 were characterized and compared to those of well-known tris(1,10-phenanthroline)rutheniun(II) [Ru(o-phen)3](PF 6)2] complex as a reference. Dinuclear Ru(II) complexes containing the conjugated bridging ligand (BL2) showed much more intense electrochemiluminescent responses than dinuclear Ru(II) complexes with the non-conjugated bridging ligand (BL1). Among the complexes with conjugated bridging ligands, [(DTDP)2Ru(bpy-CC-bpy)Ru(DTDP)2](PF 6)4 exhibited enhanced ECL intensities as high as 3.6 times greater than that of the reference, [Ru(o-phen)3](PF 6)2.

Intramolecular C-H bond activation through a flexible ester linkage

Replacing the director: A bipyridinyl ligand with an aliphatic side chain determines the regioselectivity of copper-catalyzed C-H oxidation by intramolecular effects. Because the aliphatic chain is attached through an ester linkage, the catalytic cycle can in principle be closed by transesterification. Ion-mobility mass spectrometry and isotopic labeling provide mechanistic insight not available from direct mass spectrometry experiments. Copyright

Synthesis of substituted 2,2′-bipyridines from 2-bromo- or 2-chloropyridines using tetrakis(triphenylphosphine)palladium(0) as a catalyst in a modified Negishi cross-coupling reaction

A protocol for an efficient, modified Negishi cross-coupling strategy for substituted 2,2′-bipyridines employing tetrakis(triphenylphosphine) palladium(0) as a simple, commercially available, and relatively inexpensive catalyst for both 2-bromo- and 2-chl

Benzoheterocyclic derivatives

A benzoheterocyclic derivative of the following formula [1]: and pharmaceutically acceptable salts thereof, which show excellent anti-vasopressin activity, vasopressin agonistic activity and oxytocin antagonistic activity, and are useful as a vasopressin antagonist, vasopressin agonist or oxytocin antagonist.