16952-66-2

Basic information

• Product Name: 4-AMINOPYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: 4-AMINOPYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER;4-AMINONICOTINIC ACID ETHYL ESTER;RARECHEM AL BI 1386;ethyl 4-aMinopyridine-3-carboxylate;4-Amino-3-ethoxycarbonylpyridine;Ethyl 4-amino-3-pyridinecarboxylate;Ethyl 4-aminonicotinate;3-Pyridinecarboxylic acid, 4-aMino-, ethyl ester
• CAS NO: 16952-66-2
• Molecular Formula: C₈H₁₀N₂O₂
• Molecular Weight: 166.18
• Mol File: 16952-66-2.mol

Chemical Properties

• Melting Point: 109-111℃
• Boiling Point: 300.6 °C at 760 mmHg
• Flash Point: 135.6 °C
• Appearance: /
• Density: 1.192
• Vapor Pressure: 0.00111mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: 2-8°C
• PKA: 7.14±0.12(Predicted)
• CAS DataBase Reference: 4-AMINOPYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINOPYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER(16952-66-2)
• EPA Substance Registry System: 4-AMINOPYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER(16952-66-2)

Safety Data

• Hazardous Substances Data: 16952-66-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Aminopyridine-3-carboxylic acid ethyl ester is used as a therapeutic agent for the treatment of neurological disorders such as multiple sclerosis. It facilitates nerve conduction, potentially improving the symptoms and progression of the disease.
Used in Organic Synthesis:
In the field of organic synthesis, 4-Aminopyridine-3-carboxylic acid ethyl ester serves as a valuable intermediate compound, contributing to the development of new chemical entities and pharmaceuticals.
Used in Chemical Research:
4-Aminopyridine-3-carboxylic acid ethyl ester is utilized in chemical research to explore its properties and potential applications, furthering the understanding of its role in various chemical and biological processes.

InChI:InChI=1/C8H10N2O2/c1-2-12-8(11)6-5-10-4-3-7(6)9/h3-5H,2H2,1H3,(H2,9,10)

Upstream product

• 1078-05-3 4-nitro-3-carboxypyridine 1-oxide 
• 1074-98-2 3-methyl-4-nitropyridine N-oxide 
• 1003-73-2 3-picoline-N-oxide 
• 64-17-5 ethanol 
• 141-97-9 ethyl acetoacetate 
• 17758-33-7 3-methyl-5-nitro-4(3H)-pyrimidinone 
• 7418-65-7 4-aminonicotinic acid 

Downstream Products

• 372951-29-6 ethyl 4-amido-(N-[3-phenoxy]phenylacetyl)nicotinate 
• 16952-64-0 pyrido[4,3-d]pyrimidin-4(3H)-one 
• 89533-20-0 4-aminonicotinoyl hydrazide 
• 1345539-89-0 ethyl 4-(2-fluorobenzamido)nicotinate 

Relevant articles and documents

Novel 1,3,4-oxadiazole thioether derivatives targeting thymidylate synthase as dual anticancer/antimicrobial agents

A series of novel 1,3,4-oxadiazole thioether derivatives (compounds 9-44) were designed and synthesized as potential inhibitors of thymidylate synthase (TS) and as anticancer agents. The in vitro anticancer activities of these compounds were evaluated against three cancer cell lines by the MTT method. Among all the designed compounds, compound 18 bearing a nitro substituent exhibited more potent in vitro anticancer activities with IC50 values of 0.7 ± 0.2, 30.0 ± 1.2, 18.3 ± 1.4 μM, respectively, which was superior to the positive control. In the further study, it was identified as the most potent inhibitor against two kinds of TS protein (for human TS and Escherichia coli TS, IC50 values: 0.62 and 0.47 μM, respectively) in the TS inhibition assay in vitro and the most potent antibacterial agents with MIC (minimum inhibitory concentrations) of 1.56-3.13 μg/mL against the tested four bacterial strains. Molecular docking and 3D-QSAR study supported that compound 18 can be selected as dual antitumor/antibacterial candidate in the future study.

Anthranilic acid-based inhibitors of phosphodiesterase: Design, synthesis, and bioactive evaluation

Our previous studies identified two 2-benzoylaminobenzoate derivatives 1, which potently inhibited superoxide (O2-) generation induced by formyl-l-methionyl-l-leucyl-l-phenylalanine (FMLP) in human neutrophils. In an attempt to improve their activities, a series of anthranilic acid derivatives were synthesized and their anti-inflammatory effects and underlying mechanisms were investigated in human neutrophils. Of these, compounds 17, 18, 46, 49, and 50 showed the most potent inhibitory effect on FMLP-induced release of O2- in human neutrophils with IC50 values of 0.20, 0.16, 0.15, 0.06, and 0.29 μM, respectively. SAR analysis showed that the activities of most compounds were dependent on the ester chain length in the A ring. Conversely, a change in the linker between the A and B ring from amide to sulfonamide or N-methyl amide, as well as exchanges in the benzene rings (A or B rings) by isosteric replacements were unfavorable. Further studies indicated that inhibition of O2- production in human neutrophils by these anthranilic acids was associated with an elevation in cellular cAMP levels through the selective inhibition of phosphodiesterase 4. Compound 49 could be approved as a lead for the development of new drugs in the treatment of neutrophilic inflammatory diseases.

9-Cyano-1-azapaullone (Cazpaullone), a Glycogen Synthase Kinase-3 (GSK-3) inhibitor activating pancreatic β cell protection and replication

Recently, the serine/threonine kinase glycogen synthase kinase-3 (GSK-3) emerged as a regulator of pancreatic β cell growth and survival. On the basis of the previous observation that GSK-3 inhibitors like 1-azakenpaullone promote β cell protection and re

Synthesis of a 5-alkoxypyrido[4,3-d]pyrimidin-4(3H)-one derivative via a regioselective Meisenheimer N-oxide rearrangement

The synthetic strategy towards a 5-alkoxypyrido[4,3-d]pyrimidin-4(3H)-one is described utilizing a selective N-oxidation and subsequent regioselective Meisenheimer N-oxide rearrangement as key steps.

Facile synthesis of functionalized 4-aminopyridines

The title compounds are readily available by ring transformation of nitropyrimidinone with active methylene compounds in the presence of ammonium acetate.

Synthesis and SAR of 5-, 6-, 7- and 8-aza analogues of 3-aryl-4-hydroxyquinolin-2(1H)-one as NMDA/glycine site antagonists

A series of 5-, 6-, 7- and 8-aza analogues of 3-aryl-4-hydroxyquinolin-2(1H)-one was synthesized and assayed as NMDA/glycine receptor antagonists. The in vitro potency of these antagonists was determined by displacement of the glycine site radioligand [3H]5,7-dicholorokynurenic acid ([3H]DCKA) in rat brain cortical membranes. Selected compounds were also tested for functional antagonism using electrophysiological assays in Xenopus oocytes expressing cloned NMDA receptor (NR) 1A/2C subunits. Among the 5-, 6-, 7-, and 8-aza-3-aryl-4-hydroxyquinoline-2(1H)-ones investigated, 5-aza-7-chloro-4-hydroxy-3-(3-phenoxyphenyl)quinolin-2-(1H)-one (13i) is the most potent antagonist, having an IC50 value of 110 nM in [3H]DCKA binding and a Kb of 11 nM in the electrophysiology assay. Compound 13i is also an active anticonvulsant when administered systemically in the mouse maximum electroshock-induced seizure test (ED50 = 2.3 mg/kg, IP).