170245-15-5

Usage

Uses

Used in Pharmaceutical Industry:
3H-Imidazo[4,5-c]pyridine is used as a key intermediate in the synthesis of various bioactive compounds for pharmaceutical applications. Its unique structure allows it to be incorporated into drug molecules, potentially enhancing their therapeutic effects and targeting specific biological pathways.
Used in Organic Chemistry:
3H-Imidazo[4,5-c]pyridine is used as a building block in organic chemistry for the construction of carbocyclic nucleosides. These nucleosides are important components in the development of new antiviral and anticancer drugs, as they can mimic the structure of natural nucleosides and interfere with the replication and transcription processes of viruses and cancer cells.

InChI:InChI=1/C6H5N3/c1-2-7-3-6-5(1)8-4-9-6/h1-4H,(H,8,9)

Upstream product

• 54-96-6 3,4-diaminopyridine 
• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 2770-01-6 4-chloro-1H-imidazo[4,5-c]pyridine 
• 105952-94-1 5-ethoxycarbonyliminoimidazo<4,5-c>pyridinium ylide 
• 33631-02-6 3,4-diamino-pyridin-2-ol 
• 1681-37-4 4-amino-3-nitropyridine 
• 3243-24-1 imidazo<4,5-c>pyridine-4-one 
• 89792-18-7 3,4-bis(formylamino)pyridine 
• 124-38-9 carbon dioxide 
• 1758-73-2 Aminoiminomethanesulfinic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 122-51-0 orthoformic acid triethyl ester 
• 105952-93-0 5-aminoimidazo<4,5-c>pyridinium mesitylenesulfonate 

Downstream Products

• 7239-81-8 1H-imidazo[4,5-c]pyridine-2(3H)-thione 
• 91184-02-0 1H-Imidazo[4,5-c]pyridine-N-oxide 
• 7465-42-1 3-β-D-Ribofuranosyl-3H-imidazo<4.5-c>pyridin 
• 82722-74-5 1,5-dihydro-7-nitro-4H-imidazo[4,5-c]pyridin-4-one 
• 62002-31-7 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride 
• 148720-53-0 phenyl 1,4-dihydro-4-methyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-5H-imidazo[4,5-c]pyridine-5-carboxylate 
• 148720-55-2 4-tert-Butyl-1-(2-trimethylsilanyl-ethoxymethyl)-1,4-dihydro-imidazo[4,5-c]pyridine-5-carboxylic acid phenyl ester 
• 148720-57-4 4-Phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1,4-dihydro-imidazo[4,5-c]pyridine-5-carboxylic acid phenyl ester 
• 1430418-74-8 [(copper(II))2(N-benzyl-iminodiacetate)2(5-azabenziimidazole)(H₂O)2]*H₂O 
• 78582-15-7 4-chloro-1-(2'-deoxy-β-D-erythro-pentofuranosyl)-1H-imidazo<4,5-c>pyridine 
• 78582-17-9 4-Amino-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-imidazo<4,5-c>pyridine 

Relevant academic research and scientific papers

Structural and vibrational properties of imidazo[4,5-c]pyridine, a structural unit in natural products

The molecular structures and vibrational properties of 1H-imidazo[4,5-c] pyridine in its monomeric and dimeric forms are analyzed and related to the experimental results derived from the XRD, IR, and Raman studies. The theoretical data are discussed on the basis of DFT quantum chemical calculations using the B3LYP correlation functional and 6-311G(2d,2p) basis set. This compound crystallizes in the non-centrosymmetric orthorhombic space group Fdd2. The asymmetric unit contains one molecule of 1H-imidazo[4,5-c]pyridine and disordered molecules of solvents. The molecules are organized in hydrogen-bonded chains propagating along the [1 0 -3] direction. The stability of the dimeric form arising from charge delocalization and the existence of an N-H···N intermolecular hydrogen bond has been analyzed using the natural bond orbital approach. The normal modes, which are unique for the imidazopyridine skeleton, have been identified. The spectra of other compounds containing the imidazopyridine unit have been analyzed.

Methyltrioxorhenium (MeReO3) catalyzed selective oxidation of purine and related compounds into their N-oxides

A convenient method for the selective N-oxidation of purine, 6-methylpurine, 1H-imidazo[4,5-c]pyridine, 1H-imidazo[4,5-b]pyridine, 6-chloropurine, 6-bromopurine, and 7-azaindole by H2O2 catalyzed by methyltrioxorhenium is reported.

A simple and convenient two-step, one-pot synthesis of hetero-imidazoles from nitroaminoaryls catalyzed by Ytterbium triflate

A mild two-step one-pot procedure for the conversion of ortho-nitroamino aromatic heterocycles into corresponding benzo and heteroaromatic fused imidazoles is described. The procedure utilizes iron powder, acetic acid, triethylorthoformate, and a catalytic amount of Ytterbium triflate at 75 C for the nitro group reduction and cyclization reaction. The optimum stoichiometry of each component is highlighted and the broad utility is demonstrated with high compatibility to numerous functional groups.

Family-wide analysis of aminoacyl-sulfamoyl-3-deazaadenosine analogues as inhibitors of aminoacyl-tRNA synthetases

Aminoacyl-tRNA synthetases (aaRSs) are enzymes that precisely attach an amino acid to its cognate tRNA. This process, which is essential for protein translation, is considered a viable target for the development of novel antimicrobial agents, provided species selective inhibitors can be identified. Aminoacyl-sulfamoyl adenosines (aaSAs) are potent orthologue specific aaRS inhibitors that demonstrate nanomolar affinities in vitro but have limited uptake. Following up on our previous work on substitution of the base moiety, we evaluated the effect of the N3-position of the adenine by synthesizing the corresponding 3-deazaadenosine analogues (aaS3DAs). A typical organism has 20 different aaRS, which can be split into two distinct structural classes. We therefore coupled six different amino acids, equally targeting the two enzyme classes, via the sulfamate bridge to 3-deazaadenosine. Upon evaluation of the inhibitory potency of the obtained analogues, a clear class bias was noticed, with loss of activity for the aaS3DA analogues targeting class II enzymes when compared to the equivalent aaSA. Evaluation of the available crystallographic structures point to the presence of a conserved water molecule which could have importance for base recognition within class II enzymes, a property that can be explored in future drug design efforts.

Impact of 3-deazapurine nucleobases on RNA properties

Deazapurine nucleosides such as 3-deazaadenosine (c3A) are crucial for atomic mutagenesis studies of functional RNAs. They were the key for our current mechanistic understanding of ribosomal peptide bond formation and of phosphodiester cleavage in recentl

Highly Efficient and Catalyst-Free Synthesis of Benzimidazoles in Aqueous Media

Abstract: A convenient and highly efficient, catalysts-free synthesis of benzimidazoles in an aqueous medium has been developed. The conditions of the synthesis were optimized, and its scope was successfully extended to various substrates with good to excellent yields. The experimental procedure is simple, and the products can be isolated by filtration followed by recrystallization from water.

Atmospheric CO2 promoted synthesis of N-containing heterocycles over B(C6F5)3 catalyst

B(C6F5)3 combined with atmospheric CO2 was found to be highly effective for the cyclization of ortho-substituted aniline derivatives with N,N-dimethylformamide (DMF), and a series of N-containing heterocycles including benzothiazoles, benzimidazoles, quinazolinone and benzoxazole were obtained in good to excellent yields.

Method For Preparing Nitrogen Compounds

The present invention relates to a method for preparing nitrogen compounds using carbon dioxide, and to the use of the method in the production of vitamins, pharmaceutical products, adhesives, acrylic fibres, synthetic leathers, pesticides, herbicides, antifungal agents and fertilisers. The invention also relates to a method for producing vitamins, pharmaceutical products, adhesives, acrylic fibres, synthetic leathers, pesticides, herbicides, antifungal agents and fertilisers, which includes a step of preparing nitrogen compounds using the method of the invention. The invention further relates to a method for preparing labelled nitrogen compounds using carbon dioxide and to the uses thereof.

Synthesis and Anti-herpetic Activity of Phosphoramidate ProTides

Among the many prodrug approaches aimed at delivering nucleoside monophosphates into cells, the phosphoramidate ProTide approach is one that has shown success, which has made it possible for some of the phosphoramidates to enter into clinical trials. Herein, we report the synthesis and antiviral activity of a series of phosphoramidate ProTides designed to bypass the thymidine kinase (TK) dependence of the parent nucleoside analogues. Phosphoramidate derivatives of (E)-5-(2-bromovinyl)-2′-deoxyuridine (BVDU) that contain L-alanine or pivaloyloxymethyl iminodiacetate (IDA-POM) exhibit anti-HSV-1 and anti-VZV activity in cell cultures, but they largely lost antiviral potency against TK-deficient virus strains. Among deazapurine nucleosides and their phosphoramidate derivatives, the 7-deazaadenine containing nucleosides and their phosphoramidate triester derivatives showed weak antiviral activity against VZV. Apparently, intracellular nucleotide delivery with these phosphoramidates is partly successful. However, none of the compound prodrugs showed superior activity to their parent drugs. Copyright

Structure-guided design of substituted aza-benzimidazoles as potent hypoxia inducible factor-1α prolyl hydroxylase-2 inhibitors

We report the structure-based design and synthesis of a novel series of aza-benzimidazoles as PHD2 inhibitors. These efforts resulted in compound 22, which displayed highly potent inhibition of PHD2 function in vitro.