14432-11-2

Basic information

• Product Name: 3H-Imidazo[4,5-b]pyridine, 7-nitro-, 4-oxide
• Synonyms: 3H-Imidazo[4,5-b]pyridine, 7-nitro-, 4-oxide;7-nitro-1H-iMidazo[4,5-b]pyridine 4-oxide;7-Nitro-3H-iMidazo[4,5-b]pyridine 4-oxide;4-hydroxy-7-nitroimidazo[4,5-b]pyridine
• CAS NO: 14432-11-2
• Molecular Formula: C₆H₄N₄O₃
• Molecular Weight: 180.12
• Mol File: 14432-11-2.mol

Chemical Properties

• Melting Point: 289 °C (decomp)
• Boiling Point: 602.4±58.0 °C(Predicted)
• Appearance: /
• Density: 1.89±0.1 g/cm3(Predicted)
• PKA: 3.94±0.40(Predicted)
• CAS DataBase Reference: 3H-Imidazo[4,5-b]pyridine, 7-nitro-, 4-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-Imidazo[4,5-b]pyridine, 7-nitro-, 4-oxide(14432-11-2)
• EPA Substance Registry System: 3H-Imidazo[4,5-b]pyridine, 7-nitro-, 4-oxide(14432-11-2)

Safety Data

• Hazardous Substances Data: 14432-11-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3H-Imidazo[4,5-b]pyridine, 7-nitro-, 4-oxide is used as a key intermediate in the synthesis of pharmaceuticals for its potential biological and pharmacological activities. Its unique structure and properties make it a valuable component in the development of new drugs.
Used in Research and Development:
3H-Imidazo[4,5-b]pyridine, 7-nitro-, 4-oxide is utilized in research and development for its potential applications in various fields. Scientists and researchers are exploring its properties, reactivity, and toxicity to better understand its potential uses and limitations.
Used in Chemical Reactions:
3H-Imidazo[4,5-b]pyridine, 7-nitro-, 4-oxide can be used as a reactant in various chemical reactions due to its unique structure. Its reactivity allows for the formation of new compounds and the development of novel chemical processes.
Used in Analytical Chemistry:
3H-Imidazo[4,5-b]pyridine, 7-nitro-, 4-oxide can be employed as a reference compound or a standard in analytical chemistry. Its unique properties and characteristics make it suitable for use in various analytical techniques, such as chromatography, spectroscopy, and mass spectrometry.

Upstream product

• 6863-46-3 3H-Imidazo<4,5-b>pyridine 4-N-oxide 
• 273-21-2 3H-imidazo[4,5-b]pyridine 
• 273-21-2 1H-Imidazo[4,5-b]pyridine 
• 6863-46-3 Imidazo<4,5-b>pyridine 4-Oxide 
• 452-58-4 2,3-Diaminopyridine 

Downstream Products

• 24485-01-6 5,7-dichloro-3H-imidazo<4,5-b>pyrimidine 
• 500896-84-4 2,6-dichloro-9-benzyl-1-deazapurine 
• 929533-19-7 3-benzyl-5,7-diphenyl-3H-imidazo[4,5-b]pyridine 
• 566194-66-9 5-chloro-7-(benzylsulfanyl)-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine 
• 566194-68-1 5-chloro-7-(4-nitrobenzylsulfanyl)-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine 
• 77712-93-7 7-Amino-3H-imidazo<4,5-b>pyridine 4-N-Oxide 
• 6703-44-2 1-Deazaadenine 
• 1445877-12-2 5,7-dichloro-3-(2-methyl-3-(trifluoromethyl)benzyl)-3H-imidazo[4,5-b]pyridine 
• 1445877-04-2 3-(2-methyl-3-(trifluoromethyl)benzyl)-5-morpholino-3H-imidazo[4,5-b]pyridin-7-ol 

Relevant articles and documents

New (1-deaza)purine derivatives via efficient C-2 nitration of the (1-deaza)purine ring

Nitration of substituted (1-deaza)purines using a mixture of tetrabutylammonium nitrate (TBAN) and trifluoracetic acid anhydride (TFAA) was applied to prepare nitrosubstituted (1-deaza)purines at low temperature. The nitro group influences the system twofold: 1) it activates other substituents towards nucleophilic aromatic substitution and 2) it can be substituted itself leading to a variety of di-substituted (1-deaza)purines, also via solid phase syntheses. Several of the molecules obtained were studied for their antiprotozoal activity and for interactions with the different human adenosine receptors.

Deaza analogues of adenosine as inhibitors of blood platelet aggregation

A number of deaza analogues of adenosine were prepared and tested as inhibitors of platelet aggregation induced by ADP and collagen to investigate the structure-activity relationships in this class of nucleoside analogues. The results showed that the presence of a 6-amino group and nitrogen atoms at positions 3 and 7 of the purine moiety are required for inhibitory activity.

Fluorescing Isofunctional Ribonucleosides: Assessing Adenosine Deaminase Activity and Inhibition

The enzymatic conversion of isothiazolo[4,3-d]pyrimidine-based adenosine (tzA) and 2-aminoadenosine (tz2-AA) analogues to the corresponding isothiazolo[4,3-d]pyrimidine-based inosine (tzI) and guanosine (tzG) derivatives is evaluated and compared to the conversion of native adenosine to inosine. Henri–Michaelis–Menten analyses provides the foundation for a high-throughput screening assay, and the efficacy of the assay is showcased by fluorescence-based analysis of tzA conversion to tzI in the presence of known and newly synthesized inhibitors.

Atom-Specific Mutagenesis Reveals Structural and Catalytic Roles for an Active-Site Adenosine and Hydrated Mg2+ in Pistol Ribozymes

The pistol RNA motif represents a new class of self-cleaving ribozymes of yet unknown biological function. Our recent crystal structure of a pre-catalytic state of this RNA shows guanosine G40 and adenosine A32 close to the G53–U54 cleavage site. While the N1 of G40 is within 3.4 ? of the modeled G53 2′-OH group that attacks the scissile phosphate, thus suggesting a direct role in general acid–base catalysis, the function of A32 is less clear. We present evidence from atom-specific mutagenesis that neither the N1 nor N3 base positions of A32 are involved in catalysis. By contrast, the ribose 2′-OH of A32 seems crucial for the proper positioning of G40 through a H-bond network that involves G42 as a bridging unit between A32 and G40. We also found that disruption of the inner-sphere coordination of the active-site Mg2+ cation to N7 of G33 makes the ribozyme drastically slower. A mechanistic proposal is suggested, with A32 playing a structural role and hydrated Mg2+ playing a catalytic role in cleavage.

IMIDAZOPYRIDINE DERIVATIVES AS PI3 KINASE INHIBITORS

This invention relates to the use of imidizopyridine derivatives for the modulation, notably the inhibition of the activity or function of the phosphoinositide 3' OH kinase family (hereinafter PI3 kinases), suitably, PI3Kα, PI3Kδ, PI3Kβ, and/or PI3Kγ. Suitably, the present invention relates to the use of imidizopyridines in the treatment of one or more disease states selected from: autoimmune disorders, inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, allergy, asthma, pancreatitis, multiorgan failure, kidney diseases, platelet aggregation, cancer, sperm motility, transplantation rejection, graft rejection and lung injuries. More suitably, the present invention relates to PI3Kβ selective imidizopyridine compounds for treating cancer.

Influence of the nucleobase and anchimeric assistance of the carboxyl acid groups in the hydrolysis of amino acid nucleoside phosphoramidates

Nucleoside phosphoramidates (NPs) are a class of nucleotide analogues that has been developed as potential antiviral/antitumor prodrugs. Recently, we have shown that some amino acid nucleoside phosphoramidates (aaNPs) can act as substrates for viral polymerases like HIV-1 RT. Herein, we report the synthesis and hydrolysis of a series of new aaNPs, containing either natural or modified nucleobases to define the basis for their differential reactivity. Aqueous stability, kinetics, and hydrolysis pathways were studied by NMR spectroscopy at different solution pD values (5-7) and temperatures. It was observed that the kinetics and mechanism (P-N and/or P-O bond cleavage) of the hydrolysis reaction largely depend on the nature of the nucleobase and amino acid moieties. Aspartyl NPs were found to be more reactive than Gly or β-Ala NPs. For aspartyl NPs, the order of reactivity of the nucleobase was 1-deazaadenine>7- deazaadenine>adenine>thymine≥3-deazaadenine. Notably, neutral aqueous solutions of Asp-1-deaza-dAMP degraded spontaneously even at 4°C through exclusive P-O bond hydrolysis (a 50-fold reactivity difference for Asp-1-deaza-dAMP vs. Asp-3-deaza-dAMP at pD 5 and 70°C). Conformational studies by NMR spectroscopy and molecular modeling suggest the involvement of the protonated N3 atom in adenine and 1- and 7-deazaadenine in the intramolecular catalysis of the hydrolysis reaction through the rare syn conformation. Touching (nucleo)base: A dual intramolecular catalytic influence is demonstrated by the nucleobase and carboxyl groups in the chemical hydrolysis of amino acid nucleoside phosphoramidate prodrugs (see scheme). The replacement of the adenine N1 or N7 atoms instead of the N3 atom is shown to have a conformational role in which the protonated N3 is crucial in regulating the kinetics and mechanism of nucleotide (P-N pathway) versus nucleoside (P-O pathway) formation. Copyright

2,6,8-Trisubstituted 1-deazapurines as adenosine receptor antagonists

In this study we developed a refined pharmacophore model for antagonists of the human adenosine A1 receptor, based on features of known pyrimidine and purine derivatives. The adoption of these updated criteria assisted us in synthesizing a series of 1-deazapurines with consistently high affinity as inverse agonists for the adenosine A1 receptor. These 1-deazapurines (otherwise known as 3H-imidazo[4,5-b]pyridines) were substituted at their 2- and 6-positions, yielding a series with five of the derivatives displaying Ki values in the subnanomolar range. The most potent of these, compound 10 (LUF 5978), displayed an affinity of 0.55 nM at the human adenosine A1 receptor with > 300-fold and 45-fold selectivity toward A2A and A3 receptors, respectively. Compound 14 (LUF 5981, Ki = 0.90 nM) appeared to have the best overall selectivity with respect to adenosine A2A (> 200-fold) and A 3 (700-fold) receptors.