57062-14-3

Usage

Physical form

Yellow-brown crystalline powder

Melting point

205-212°C

Uses

Intermediate in the production of pharmaceuticals, dyes, and agricultural chemicals; building block in organic synthesis; preparation of pyridine-based molecules; catalyst in various chemical reactions

Reactivity

Strong and selective towards primary and secondary amino groups

Safety precautions

Can be harmful if ingested, inhaled, or absorbed through the skin. Proper protective equipment and handling procedures should be followed.

Upstream product

• 499-80-9 pyridine-2,4-dicarboxylic acid 

Downstream Products

• 117517-22-3 N,N'-diethyl-2,4-pyridinedicarboxamide 
• 21071-04-5 2,4-Bis(hydroxymethyl)pyridin 
• 501938-32-5 2,4-dibenzoylpyridine 
• 947414-89-3 2,4-bis(1-phenyl-1-pyrrolylmethyl)pyridine 
• 947414-88-2 2,4-bis(phenylhydroxymethyl)pyridine 
• 20857-17-4 2,4-diacetylpyridine 
• 1246534-88-2 C₃₃H₂₅N₅O₄ 
• 1246534-81-5 C₂₃H₂₁N₅O₄ 
• 1246534-80-4 C₂₃H₂₁N₅O₆ 
• 1246534-87-1 C₂₅H₂₅N₅O₆ 
• 1246534-84-8 C₂₃H₂₁N₅O₆ 
• 1246534-79-1 C₂₁H₁₇N₅O₄ 
• 1246534-83-7 C₂₁H₁₅Cl₂N₅O₄ 
• 1246534-82-6 C₂₃H₂₁N₅O₄ 

Relevant academic research and scientific papers

Discovery of novel dehydroabietic acid derivatives as DNA/BSA binding and anticancer agents

To explore the biological properties of rosin derivatives, two dehydroabietic acid derivatives N-(5-dehydroabietyl-1,3,4-thiadiazole)-yl-pyridine-2-carboxamide (DTPC) and di-N-(5-dehydroabietyl-1,3,4-thiadiazole)-yl-pyridine-2,6-carboxamide (DDTPC) with 1,3,4-thiadiazole, pyridine and amide moieties were designed and synthesized according to superposition principle of activity group. They interact with calf thymus DNA (CT DNA) via intercalation based on the results of circular dichroism (CD) and fluorescence spectroscopy, DNA denaturation and viscosity studies. Fluorescence and CD spectral experiments indicate that they might be transported and stored by protein like bovine serum albumin (BSA). MTT assay was further carried out to examine their cytotoxicity, they both showed selective cytotoxicity and DTPC exhibited better cytotoxicity. The antiproliferative effect of DTPC toward A431 cell line was stronger than that of clinically used cisplatin and oxaliplatin. In addition, the cytotoxicity of DTPC and DDTPC was closely related with their DNA binding ability.

Identification and Optimization of the First Highly Selective GLUT1 Inhibitor BAY-876

Despite the long-known fact that the facilitative glucose transporter GLUT1 is one of the key players safeguarding the increase in glucose consumption of many tumor entities even under conditions of normal oxygen supply (known as the Warburg effect), only

Synthesis and Biological Evaluation of Oral Prodrugs Based on the Structure of Gemcitabine

A series of oral prodrugs based on the structure of gemcitabine (2′,2′-difluorodeoxycytidine) were synthesised by introducing an amide group at the N4-position of the cytidine ring. A total of 16 compounds were obtained, and their chemical and biological characteristics were evaluated. The half-maximal inhibitory concentrations (IC50s) for most of these compounds were higher than that of gemcitabine in vitro. Compounds 5d and 5m, the representative compounds, were examined in terms of their physiological stabilities and pharmacokinetics. Compound 5d showed good stability in PBS and simulated intestinal fluid, and an analysis of its pharmacokinetics in mice suggested that the introduction of an amide group to gemcitabine could greatly improve its bioavailability. Further evaluation of compound 5din vivo showed that this compound possesses higher activity than gemcitabine against the growth of HepG2 human hepatocellular carcinoma cells and HCT-116 colon adenocarcinoma cells with less toxicity to animals. These results suggest that compound 5d could be further developed as a potential oral anticancer agent for clinical applications in which gemcitabine is currently used. A series of oral prodrugs based on the structure of gemcitabine were synthesized. Physiological and metabolic stabilities, pharmacokinetics and antitumor activities were evaluated for representative compounds.

Synthesis and structural characterisation of 2,4-bis(5-aryl-1,3,4-oxdiazol- 2-yl) pyridine derivatives

A convenient synthesis of 2,4-bis (5-aryl-1,3,4-oxdiazol-2-yl) derivatives of pyridine by the POCl3-mediated cyclodehydration of a variety of pyridine-2,4-dicarboxylic dihydrazides has been developed. The 20 novel intermediates and target molecules were characterised by IR, 1H NMR, MS and elemental analysis.

Aromatic and nonaromatic pyriporphyrins

Pyriporphyrins with three different orientations for the pyridine moiety have been prepared using a '3 + 1' strategy. The nonaromatic pyriporphyrins are stable so long as phenyl substituents are present at the meso-positions adjacent to the pyridine ring. An aromatic dihydropyriporphyrin with an external CO 2Ph protective group has also been prepared from 2,4- pyridinedicarbaldehyde.

Self-assembly of a pyridyl derivative and its silver complex: Formation of a liquid crystalline phase and organogels

Self-assembling behavior of N,N′-didodecyl-3,5-pyridinedicarboxamide and its silver complex has been studied. They act as gelators in solution and gelate a variety of organic solvents. Though the silver complex exhibits lower gelation abilities for halogenated and aromatic solvents, long-term stability is achieved for ethanol and acetone gels. Moreover, the silver complex exhibits a smectic A phase on cooling while a single component of N,N′-didodecyl-3-5- pyridinedicarboxamide exhibits no mesomorphic behavior. The XRD pattern for the complex shows that the layer spacing of the SA phase is 37 A.

Do high-spin topology rules apply to charged polyradicals? Theoretical and experimental evaluation of pyridiniums as magnetic coupling units

Ab initio calculations on pyridine and pyridinium analogues of m-xylylene indicate that the neutral heterocycle is essentially equivalent to benzene as a ferromagnetic coupling unit, while the cationic pyridiniums behave much differently. Depending on the substitution pattern, a protonated pyridine can serve as a ferromagnetic coupling unit or an antiferromagnetic coupling unit. Both valence bond and molecular orbital arguments provide qualitative rationalizations of these results. In an effort to test the theoretical predictions, bis(trimethylenemethane) analogues of the pyridine and pyridinium biradicals were synthesized and analyzed by electron paramagnetic resonance spectroscopy. General support for the theoretical predictions is obtained.

Behavior of Pyridinium Salts Obtained from Derivatives of Pyridinedicarboxylic Acids in Basic Solutions. Addition of Hydroxide or Alkoxide To Form 1,2-Dihydropyridine Intermediates

The N-alkylated pyridinium salts obtained from the diethyl esters, N-ethyl amides, and N,N-diethyl amides of pyridine-3,5-dicarboxylic acid exhibit ultraviolet absorptions of moderate intensity in the region of 350 nm when dissolved in 95percent ethanol.This absorption increases in intensity on addition of base and disappears on acidification of the solutions.It is not observed in rigorously dried solvents like chloroform or methylene chloride.By 1H NMR spectroscopy it has been shown that a 1,2-dihydropyridine is formed reversibly by addition of hydroxide (or methoxide) to the 2-position of the pyridinium salts.Concurrently with the formation of these intermediates, proton-deuterium exchange (in deuterated solvents) occurs, possibly via betaines formed by base-induced deprotonation at the 2-position of the pyridinium salts.The corresponding derivatives of pyridine-2,5- and -3,5-dicarboxylic acids do not display this behavior.