13362-30-6

Usage

Uses

Used in Organic Synthesis:
2-AMINO-ISONICOTINIC ACID ETHYL ESTER is used as a key intermediate for the synthesis of various organic compounds. Its versatile chemical structure allows it to be a valuable building block in the creation of a wide range of molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-AMINO-ISONICOTINIC ACID ETHYL ESTER is used as a crucial intermediate in the development of new drugs. Its unique chemical properties make it a valuable component in the synthesis of various medicinal compounds.
Used in Agrochemicals:
2-AMINO-ISONICOTINIC ACID ETHYL ESTER is also utilized in the agrochemical industry for the synthesis of pesticides and other agricultural chemicals. Its role in this industry is to contribute to the development of effective and environmentally friendly products.
Used in Dyestuff Industry:
In the dyestuff industry, 2-AMINO-ISONICOTINIC ACID ETHYL ESTER is used as an intermediate for the production of various dyes and pigments. Its chemical properties make it suitable for creating a wide array of colorants used in different applications.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 44, p. 78, 2001 DOI: 10.1021/jm001034k

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

Upstream product

• 54221-95-3 2-(acetylamino)isonicotinic acid 
• 64-17-5 ethanol 
• 5327-32-2 2-acetylamino-4-methylpyridine 
• 6313-54-8 2-chloroisonicotinic acid, 
• 13362-28-2 2-aminoisonicotinic acid 
• 54453-93-9 ethyl 2-chloroisonicotinate 
• 475057-16-0 (E)-3-[8-({[4-(tert-Butyl)-1,3-thiazol-2-yl]amino}carbonyl)-2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl]-2-propenoic acid 
• 695-34-1 2-Amino-4-methylpyridine 

Downstream Products

• 105250-17-7 2-amino-4-hydroxymethylpyridine 
• 372147-49-4 imidazo[1,2-a]pyridine-7-carboxylic acid ethyl ester 
• 480459-11-8 [3-(2-aminopyrimidin-4-yl)-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-7-yl]methanol 
• 480453-78-9 [2-(4-fluorophenyl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyridin-7-yl]methanol 
• 480453-85-8 4-[7-[(dimethylamino)methyl]-2-(4-fluorphenyl)imidazo[1,2-α]pyridine-3-yl]pyrimidin-2-amine 
• 918955-28-9 methanesulfonic acid 3-(2-amino-pyrimidin-4-yl)-2-(4-fluoro-phenyl)-imidazo[1,2-a]pyridin-7-ylmethyl ester 
• 918955-26-7 [2-(4-fluoro-phenyl)-3-(2-methoxy-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-7-yl]-methanol 
• 918955-22-3 [2-(4-fluoro-phenyl)-3-(2-methylamino-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-7-yl]-methanol 
• 480457-97-4 [2-(4-fluorophenyl)-3-(2-methanesulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridin-7-yl]methanol 
• 918955-34-7 methanesulfonic acid 2-(4-fluoro-phenyl)-3-(2-methoxy-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-7-ylmethyl ester 
• 918955-29-0 methanesulfonic acid 2-(4-fluoro-phenyl)-3-(2-methylamino-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-7-ylmethyl ester 
• 918955-25-6 [3-(2-benzyloxy-pyrimidin-4-yl)-2-(4-fluoro-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methanol 
• 918955-21-2 [3-(2-benzylamino-pyrimidin-4-yl)-2-(4-fluoro-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methanol 
• 918955-24-5 [3-[2-(benzyl-methyl-amino)-pyrimidin-4-yl]-2-(4-fluoro-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methanol 

Relevant academic research and scientific papers

Synthesis method of 2-aminopyridine-4-ethyl formate intermediate

The invention discloses a synthesis method of a 2-aminopyridine-4-ethyl formate intermediate. The synthesis method includes the following steps of mixing 2-amino-4-methylpyridine with water, heating the mixture to 60-80 DEG C, adding a Cu-Ce-Bi-SiO2 catalyst, stirring the mixture above, then introducing O2 into the mixture, stopping introduction of O2 after a reaction is completed, conducting filtering after the temperature of the mixture drops to room temperature, and adjusting the pH of a filtrate to be 9-10; adding ethyl alcohol, conducting reduced pressure distillation to remove ethyl alcohol after a heating reflux reaction has been carried out for 1-2 hours, utilizing dichloromethane for extraction several times, combining organic phases, removing dichloromethane and obtaining 2-aminopyridine-4-ethyl formate. The synthesis method is simple in operation, mild in condition and high in product purity and product yield and generates few by-products.

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.

Highly efficient one-pot amination of carboxylate-substituted nitrogen-containing heteroaryl chlorides via Staudinger reaction

An efficient one-pot method for the synthesis of tert-butyl 6-aminonicotinate (5) is described. The key transformation involves displacement of the chloro group in tert-butyl 6-chloronicotinate (2) with azide followed by a Staudinger reaction. The scope of this methodology is further extended for the synthesis of a series of carboxylate-substituted heteroaryl amines. In particular, we synthesized tert-butyl carboxylate-substituted amino-pyridine, -pyridazine, and -pyrazine. In addition to one-pot conversion, short reaction time, simplicity of operation, ease of purification, and good yields are the key advantages of this methodology.

Synthesis and SAR of 2-(4-fluorophenyl)-3-pyrimidin-4-ylimidazo[1,2-a]pyridine derivatives as anticoccidial agents

Compounds 10a-10d and 10i are very potent inhibitors of Eimeria tenella cGMP-dependent protein kinase (0.081-0.32 nM) and are very efficacious antiparasitic agents in vivo when administered to chickens at 12.5-25 ppm levels in the feed.

Design and synthesis of potent, orally active, inhibitors of carboxypeptidase U (TAFIa)

A series of 3-mercapto-propionic acid derivatives that function as reversible inhibitors of carboxypeptidase U have been prepared. We present a successful design strategy using cyclic, low basicity guanidine mimetics resulting in potent, selective and bioavailable inhibitors of carboxypeptidase U (TAFIa).

Drug efflux pump inhibitor

A medicament for preventive and/or therapeutic treatment of a microbial infection which comprises as an active ingredient a compound represented by the following general formula (I): wherein, R1 and R2 represent hydrogen atom, a halogen atom, hydroxyl group or the like, W1 represents —CH═CH—, —CH2O—, —CH2CH2— or the like; R3 represents hydrogen atom, a halogen atom, hydroxyl group or an amino group; R4 represents hydrogen atom, a group of —OZ0-4R5 (Z0-4 represents an alkylene group, a fluorine-substituted alkylene group or a single bond, and R5 represents a cyclic alkyl group, an aryl group or the like); W2 represents a single bond or —C(R8)═C(R9)— (R8 and R9 represent hydrogen atom, a halogen atom, a lower alkyl group or the like, Q represents an acidic group, but W2 and Q may together form vinylidenethiazolidinedione or an equivalent heterocyclic ring; m and n represent an integer of 0 to 2, and q represents an integer of 0 to 3.

Synthesis and biological evaluation of novel pyrazoles and indazoles as activators of the nitric oxide receptor, soluble guanylate cyclase

Database searching and compound screening identified 1-benzyl-3-(3-dimethylaminopropyloxy)-indazole (benzydamine, 3) as a potent activator of the nitric oxide receptor, soluble guanylate cyclase. A comprehensive structure-activity relationship study surrounding 3 clearly showed that the indazole C-3 dimethylaminopropyloxy substituent was critical for enzyme activity. However replacement of the indazole ring of 3 by appropriately substituted pyrazoles maintained enzyme activity. Compounds were evaluated for inhibition of platelet aggregation and showed a general lipophilicity requirement. Aryl-substituted pyrazoles 32, 34, and 43 demonstrated potent activation of soluble guanylate cyclase and potent inhibition of platelet aggregation. Pharmacokinetic studies in rats showed that compound 32 exhibits modest oral bioavailability (12%) Furthermore 32 has an excellent selectivity profile notably showing no significant inhibition of phosphodiesterases or nitric oxide synthases.

Substituted pyrimidinone and pyridone compounds and methods of use

Selected novel substituted pyrimidinone and pyridone compounds are effective for prophylaxis and treatment of diseases, such as TNF- alpha , IL-1 beta , IL-6 and/or IL-8 mediated diseases, and other maladies, such as pain and diabetes. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving inflammation, pain, diabetes and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

Benzene derivatives and pharmaceutical composition

A benzene derivative of the formula (I): STR1 wherein R 1 is hydrogen, C 1-6 -alkyl, C 1-6 -haloalkyl, --NH 2, --NHR 21 ; R 2 is hydroxyl, --OR 22, three- to seven-membered saturated cycloaliphatic amino optionally interrupted by one or more nitrogen, oxygen or sulfur atoms, --NHR 23, --N(R 24) 2, --NH 2 ; R 4 is hydrogen, C 1-6 -alkyl, or --C( O)R 25 ; R 7 is --CO--, --SO 2 --; R 8 is --CO--, single bond; R 12 is --R 11 --R 5 ; R 11 is --N(R 5)--, --NH--, --O--, --N(R 26)--, --N(C( O)R 27)--, --N(C( O)NH 2)--, --N(C( O)NHR 28)--; R 13 is hydrogen, C 1-6 -alkyl, C 1-6 -haloalkyl, --NHC( O)(CH 2) m C 6 H 5, --NHC( O)R 29, --NHC( O)CH(C 6 H 5) 2, --NH 2, --NHR 30, --(CH 2) n C 6 H 5 ; Z is C, CH, N; A is CH, N; R 5 is hydrogen, --CH 2 C 6 H 4 COOH, --CH 2 C 6 H 4 COOR 31, --CH 2 C 6 H 4 OH, --CH 2 C 6 H 4 OR 32, --CH 2 C 6 H 4 NH 2, --CH 2 C 6 H 4 N(R 33) 2, --CH 2 C 6 H 4 -azole, --CH 2 C 6 H 4 NHR 34, --CH 2 C 6 H 4 C 6 H 4 R 14 ; R 14 is azole, --COOH; R 21 to R 34 are independently C 1-6 -alkyl or C 1-6 -haloalkyl; m is 0 to 6; n is 0 to 6; t is 0 or 1, with the proviso that when Z is N, R 5 is hydrogen, --CH 2 C 6 H 4 COOH, --CH 2 C 6 H 4 COOR 31, --CH 2 C 6 H 4 OH, --CH 2 C 6 H 4 OR 32, --CH 2 C 6 H 4 NH 2, --CH 2 C 6 H 4 N(R 33) 2, --CH 2 C 6 H 4 -azole, or --CH 2 C 6 H 4 NHR 34, or a salt thereof, and a pharmaceutical composition comprising said benzene derivative or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier are disclosed.