88312-64-5

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-amino-5-nitronicotinate is used as a key intermediate in the synthesis of polyfunctionalized benzo[d]thiazole and thiazolo[5,4-b]pyridine derivatives, which have potential applications as pharmaceutical agents. These heterocyclic compounds exhibit a wide range of biological activities, including antimicrobial, anticancer, and antiviral properties, making them promising candidates for the development of new drugs.
Used in Organic Synthesis:
Methyl 2-amino-5-nitronicotinate is used as a versatile building block in organic synthesis for the preparation of various heterocyclic compounds. Its reactivity allows for the formation of diverse functional groups and structural motifs, which can be further elaborated upon to access a wide range of target molecules with potential applications in various fields, such as materials science, agrochemistry, and medicinal chemistry.

Upstream product

• 14080-32-1 5-nitropyrimidine 
• 105-34-0 methyl 2-cyanoacetate 
• 14667-47-1 methyl 2-aminonicotinate 
• 5345-47-1 2-aminopyridin-3-carboxylic acid 

Relevant academic research and scientific papers

Discovery and Optimization of a Compound Series Active against Trypanosoma cruzi, the Causative Agent of Chagas Disease

Chagas disease is caused by the protozoan parasite Trypanosoma cruzi. It is endemic in South and Central America and recently has been found in other parts of the world, due to migration of chronically infected patients. The current treatment for Chagas disease is not satisfactory, and there is a need for new treatments. In this work, we describe the optimization of a hit compound resulting from the phenotypic screen of a library of compounds against T. cruzi. The compound series was optimized to the level where it had satisfactory pharmacokinetics to allow an efficacy study in a mouse model of Chagas disease. We were able to demonstrate efficacy in this model, although further work is required to improve the potency and selectivity of this series.

TREATMENT OF CHAGAS DISEASE

The invention provides compounds of the formula: wherein L1 and L2 are independently selected from O and S; R1 is C3-C6straight or branched alkyl, C3-C7cycloalkyl, C5-C7cycloalkenyl, adamantly, phenyl or saturated heterocyclyl, any of which being optionally substituted; R2 is H, methyl or ethyl; R5 is NRxCORy, NRxRy, CH2COCH3, CH2C≡N, or a 5- or 6-membered heteroaryl group which is optionally substituted; X, Y and Z are independently N or CH; Rx is independently H or C1-C4alkyl; Ry is independently H, CrC4alkyl, phenyl or benzyl, either of which is optionally substituted; n is 0-3; salts, hydrates and N-oxides, wherein the optional substituents are further defined in the claims. The compounds have utility in the prophylaxis or treatment of trypanosomal diseases, such as T. cruzi (Chagas disease).

Rational multistep synthesis of a novel polyfunctionalized benzo[d]thiazole and its thiazolo[5,4-b]pyridine analogue

Reliable synthetic routes were studied for an access to a novel polyfunctionalized 6-amino-2-cyanobenzo[d]thiazole-5-carboxylate ester (1) and its analogue 5-amino-2-cyanothiazolo[5,4-b]pyridine-6-carboxylate ester (2). Both compounds 1 and 2 are functionalized as molecular bricks for the synthesis of innovative molecular systems. Part of the chemistry performed in this study was achieved under microwave irradiation.

NOVEL ANTIMALARIA AGENT CONTAINING HETEROCYCLIC COMPOUND

Disclosed is an antimalarial agent containing a compound represented by the formula: [wherein A1 represents a 3-pyridyl group that may have a substituent, a 6-quinolyl group that may have a substituent, or the like; X1 represents a group represented by the formula -C(=O)-NH- or the like; E represents a furyl group, a thienyl group or a phenyl group; with the proviso that A1 may have one to three substituents, and E has one of two substituents] or a salt thereof or hydrates thereof.

NOVEL ANTIFUNGAL AGENT COMPRISING HETEROCYCLIC COMPOUND

The present invention provides an antifungal agent represented by the formula: [wherein A1 represents a 3-pyridyl group which may have a substituent, a quinolyl group which may have a substituent, or the like; X1 represents a group represented by the formula -NH-C(=O)-, a group represented by the formula -C(=O)-NH-, or the like; E represents a furyl group, a thienyl group, a pyrrolyl group, a phenyl group, a pyridyl group, a tetrazolyl group, a thiazolyl group or a pyrazolyl group; with the proviso that A1 may have 1 to 3 substituents, and E has one or two substituents].

Ring transformations in reactions of heterocyclic compounds with nucleophiles. The conversion of 5-nitropyrimidine into pyridine derivatives by CH-active nitriles

Nitriles R-CH2CN where R is CN, SO2C6H5, C6H4-NO2-p, C6H4-CF3-m, are effective reagents for converting 5-nitropyrimidine (1) into 2-amino-5-nitro-3-R-pyridines (7).In reactions of 1 with cyanoacetic acid derivatives (methyl, ethyl, tert-butyl esters), 3-c