3073-30-1

Usage

Uses

Used in Pharmaceutical Industry:
6-AMINO-3,5-DINITROPYRIDINE is used as a key intermediate compound for the synthesis of various pharmaceutical agents. Its unique structure allows it to be a building block for the development of new drugs targeting specific receptors in the nervous system.
6-AMINO-3,5-DINITROPYRIDINE is used as a precursor for the preparation of antagonists for [application type] NMDA/glycine, AMPA, and Kainate Receptors [application reason] to modulate the activity of these receptors, which play crucial roles in various neurological processes and conditions.
In the development of antagonists for these receptors, 6-AMINO-3,5-DINITROPYRIDINE serves as a vital component in the synthesis process, enabling the creation of compounds that can potentially treat neurological disorders and conditions related to the overstimulation or dysfunction of these receptors.
Additionally, due to its versatile chemical structure, 6-AMINO-3,5-DINITROPYRIDINE may also be used in other applications within the pharmaceutical and chemical industries, such as the synthesis of other bioactive molecules, dyes, or materials with specific properties. However, further research and development are required to explore these potential applications fully.

Preparation

Ritter202 found that nitration of 2-amino-5-nitropyridine gave the 2-nitrarnino compound and further reaction gave 2-amino-3,5-dinitropyridine.

InChI:InChI=1/C5H4N4O4/c6-5-4(9(12)13)1-3(2-7-5)8(10)11/h1-2H,(H2,6,7)

Upstream product

• 940-06-7 3,5-dinitropyridine 
• 15367-00-7 5-nitro-2-nitraminopyridine 
• 2578-45-2 2-chloro-3,5-dinitropyridine 
• 6936-39-6 2-nitro-2-nitraminopyridine 
• 7664-93-9 sulfuric acid 
• 4214-75-9 2-amino-3-nitropyridine 
• 6635-86-5 2-amino-4-methyl-3-nitropyridine 
• 504-29-0 2-aminopyridine 
• 4214-76-0 5-nitro-pyridin-2-ylamine 

Downstream Products

• 39771-28-3 2,4,6-triamino-3,5-dinitropyridine 
• 34981-11-8 2,6-diamino-3,5-dinitropyridine 
• 3537-14-2 5-nitro-pyridine-2,3-diamine 
• 3537-09-5 6-nitro-1⁽³⁾H-imidazo[4,5-b]pyridine 
• 1186224-16-7 2-(4-fluorophenyl)-3H-imidazo[4,5-b]pyridin-6-amine 
• 1186224-04-3 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridin-6-amine 
• 1186224-26-9 2-(4-bromophenyl)-3H-imidazo[4,5-b]pyridin-6-amine 
• 1186224-30-5 2-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridin-6-amine 
• 1186224-54-3 2-(3-bromophenyl)-3H-imidazo[4,5-b]pyridin-6-amine 
• 1186223-07-3 2,6-difluoro-N-(2-phenyl-3H-imidazo[4,5-b]pyridin-6-yl)-3-(propylsulfonamido)benzamide 
• 1186224-51-0 2-(2-fluorophenyl)-3H-imidazo[4,5-b]pyridin-6-amine 
• 1186224-61-2 2-(2-chlorophenyl)-3H-imidazo[4,5-b]pyridin-6-amine 
• 1186224-71-4 2-(2-bromophenyl)-3H-imidazo[4,5-b]pyridin-6-amine 
• 1186224-20-3 2-(3,4-dichlorophenyl)-3H-imidazo[4,5-b]pyridin-6-amine 

Relevant academic research and scientific papers

Nucleophilic dearomatization of 4-aza-6-nitrobenzofuroxan by CH acids in the synthesis of pharmacology-oriented compounds

4-Aza-6-nitrobenzofuroxan (ANBF) reacts with 1,3-dicarbonyl compounds and other CH acids to give carbon-bonded 1,4-adducts - 1,4-dihydropyridines fused with furoxan ring. In the case of most acidic β-diketones, which exist mainly in the enol form in polar solvents, the reactions proceed in the absence of any added base emphasizing the highly electrophilic character of ANBF. The resulting compounds combine in one molecule NO-donor furoxan ring along with a pharmacologically important 1,4-dihydropyridine fragment and therefore can be considered as prospective platforms for the design of pharmacology-oriented heterocyclic systems.

NOVEL INHIBITORS OF BACTERIAL GLUTAMINYL CYCLASES FOR USE IN THE TREATMENT OF PERIODONTAL AND RELATED DISEASES

The present invention relates to novel compounds which are particularly useful as inhibitors of bacterial glutaminyl cyclases (bacQC); pharmaceutical compositions comprising such compounds; compounds and/or pharmaceutical compositions for use in methods for treatment, in particular for use in the treatment of periodontitis and related conditions; as well as to crystals comprising bacterial glutaminyl cyclases, methods for identifying candidate compounds which may associate with the binding pocket of a bacQC and/or are bacQC inhibitors.

Theoretical and experimental NMR data of 3,5-dinitro-2-(2-phenylhydrazinyl) pyridine and of its 4- and 6-methyl derivatives

3,5-Dinitro-2-(2-phenylhydrazinyl)pyridine and its methyl derivatives: 4-methyl-3,5-dinitro-2-(2-phenylhydrazinyl)pyridine and 6-methyl-3,5-dinitro-2- (2-phenylhydrazinyl)pyridine were synthesized and characterized by 1H NMR and 13C NMR. Calculations were also performed where the above molecules were optimized using the methods of density functional theory (DFT) with 6-31G(d,p) and 6-311G(d,p) basis sets. For all molecules studied, the lowest energy was obtained using the 6-311G(d,p) basis set. The GIAO/DFT (Gauge Invariant Atomic Orbitals/Density Functional Theory) calculations on the 6-311G and 6-311++G and 6-311G* basis sets were carried out to determine proton and carbon chemical shifts and to find they were close to the experimental values. It has been also found that intramolecular hydrogen bonding exists between hydrogen atom (in 2-NH group) and oxygen atom (pyridine-3-NO2). Moreover, resonances between pyridine ring and electron withdrawing 3-nitro group as well between that ring and the lone electron pair of NH group favor a co-planarity of the structure; this means a chelate ring created by above-mentioned intramolecular hydrogen bond is almost co-planar with pyridine ring.

IMDIZO [4. 5-B] PYRIDINE DERIVATIVES USED AS RAF INHIBITORS

Compounds of Formula I are useful for inhibition of Raf kinases. Methods of using compounds of Formula I and stereoisomers and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

HETEROARYL DERIVATIVES AS PROTEIN KINASE INHIBITORS

Objects of the present invention are the compounds of formula I their pharmaceutically acceptable salts, enantiomeric forms, diastereoisomers and racemates, the preparation of the above-mentioned compounds, medicaments containing them and their manufacture, as well as the use of the above-mentioned compounds in the control or prevention of illnesses such as cancer.

Phenyl-aza-benzimidazole compounds for modulating IgE and inhibiting cellular proliferation

The present invention is directed to small molecule inhibitors of the IgE response to allergens, which are useful in the treatment of allergy and/or asthma or any diseases where IgE is pathogenic. This invention also relates to phenyl-aza-benzimidazole molecules that are cellular proliferation inhibitors and thus are useful as anticancer agents. This invention further relates to small molecules which suppress cytokines and leukocytes.

8-aza, 6-aza and 6,8-diaza-1,4-dihydroquinoxaline-2,3-diones and the use thereof as antagonists for the glycine/NMDA receptor

Disclosed is a method of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma or hypoglycemia. The method comprises administering to an animal a compound of the formula: STR1 or a pharmaceutically acceptable salt thereof; wherein n is zero or 1; R 4, R 5, R 6 are independently hydrogen, nitro, amino, halo, haloalkyl, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, azido, acylamino, alkylsulfonyl, aryl, substituted aryl, heteroaryl, alkoxy, trialkylsilyl-substituted alkoxy, aryloxy, substituted aryloxy, heteroaryloxy, a heterocyclic group, a heterocyclicoxy group, aralkoxy, or haloalkoxy; and R c and R d are defined in the specification. These compounds have high binding to the glycine site of the NMDA receptor.

5-(N-oxyaza)-7-substituted-1,4-dihydroquinoxaline-2,3-diones: Novel, systemically active and broad spectrum antagonists for NMDA/glycine, AMPA, and kainate receptors

A group of 5-aza-7-substituted-1,4-dihydroquinoxaline-2,3-diones (QXs) and the corresponding 5-(N. oxyaza)-7-substituted QXs were prepared and evaluated as antagonists of ionotropic glutamate receptors. The in vitro potency of these QXs was determined by inhibition of [3H]-5,7- dichlorokynurenic acid ([3H]DCKA) binding to N-methyl-D-aspartate (NMDA)/glycine receptors, [3H]-(S)-α-amino-3-hydroxy-5-methyl-4- isoxazolepropionic acid ([3H]AMPA) binding to AMPA receptors, and [3H]kainate ([3H]KA) binding to KA receptors in rat brain membranes. 5-(N- Oxyaza)-QXs 12a-e all have low micromolar or submicromolar potency for NMDA/glycine receptors and low micromolar potencies for AMPA and KA receptors. QXs 12a-e display 2-12-fold selectivity for NMDA/glycine receptors compared to AMPA receptors, and ~2-fold difference between AMPA and KA potency. In contrast to other QXs that either show high selectivity for NMDA (such as ACEA 1021) or AMPA (such as NBQX) receptors, these molecules are broad spectrum antagonists of ionotropic glutamate receptors. 7-Nitro-5-(N- axyaza)-QX (12e) is the most potent inhibitor among 12a-e, having IC50 values of 0.69, 1.3, and 2.4 μM at NMDA, AMPA, and KA receptors, respectively. In functional assays on glutamate receptors expressed in oocytes by rat cerebral cortex poly(A+) RNA, 7-chloro-5-(N-oxyaza)-QX (12a) and 7-nitro-5(N-oxyaza)-QX (12e) have K(b) values of 0.63 and 0.31 μM for NMDA/glycine receptors, and are 6- and 4-fold selective for NMDA over AMPA receptors, respectively. 5-(N-Oxyaza)-7-substituted-QXs 12a-e all have surprisingly high in vivo potency as anticonvulsants in a mouse maximal electroshock-induced seizure (MES) model. 7-Chloro-5-(N-oxyaza)-QX (12a), 7- bromo-5-(N-oxyaza)-QX (12b), and 7-methyl-5-(N-oxyaza)-QX (12c) have ED50 values of 0.82, 0.87, and 0.97 mg/kg iv, respectively. The high in vivo potency of QXs 12a-e is particularly surprising given their low log P values (~ -2.7). Separate studies indicate that QXs 12a and 12e are also active in vive as neuroprotectants and also have antinociceptive activity in animal pain models. In terms of in vivo activity, these 5-(N-oxyaza)-7-substituted- QXs are among the most potent broad spectrum ionotropic glutamate antagonists reported.

6-AMINO SUBSTITUTED IMIDAZO[4,5-BIPYRIDINES AS ANGIOTENSIN II ANTAGONISTS

Substituted imidazo[4,5-b]pyridines of structural formula: STR1 are angiotensin II antagonists useful in the treatment of hypertension and congestive heart failure.