91184-02-0

Basic information

• Product Name: 3H-IMidazo[4,5-c]pyridine, 5-oxide
• Synonyms: 3H-IMidazo[4,5-c]pyridine, 5-oxide;1H-iMidazo[4,5-c]pyridine 5-oxide;5-Oxido-1H-imidazo[4,5-c]pyridin-5-ium
• CAS NO: 91184-02-0
• Molecular Formula: C₆H₅N₃O
• Molecular Weight: 135.1234
• Mol File: 91184-02-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3H-IMidazo[4,5-c]pyridine, 5-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-IMidazo[4,5-c]pyridine, 5-oxide(91184-02-0)
• EPA Substance Registry System: 3H-IMidazo[4,5-c]pyridine, 5-oxide(91184-02-0)

Safety Data

• Hazardous Substances Data: 91184-02-0(Hazardous Substances Data)

Upstream product

• 272-97-9 Imidazo<4,5-c>pyridin 
• 7732-18-5 water 
• 7722-84-1 dihydrogen peroxide 
• 54-96-6 3,4-diaminopyridine 

Downstream Products

• 82722-74-5 1,5-dihydro-7-nitro-4H-imidazo[4,5-c]pyridin-4-one 
• 1078168-19-0 C₇H₄N₄ 
• 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 
• 6811-77-4 3-deazaadenine 

Relevant articles and documents

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

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.

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.

3-nifro-3-deaza-2′-deoxyadenosine as a versatile photocleavable 2′-deoxyadenosine mimic

A new photocleavable 2′-deoxyadenosine mimic, 3-nitro-3-deaza-2′-deoxyadenosine (NidA), was prepared and introduced into DNA fragments via its 6-O-trimethylphenyl precursor phophoramidite. Photocleavage of the resulting oligonucleotide is highly efficient

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.

Piperazinyl derivatives of purines and isosteres thereof as hypoglycemic agents

There are disclosed certain 6-piperazinopurines and heteroaromatic derivatives thereof which have oral hypoglycemic acitivity and with such ability to lower blood sugar are useful in the treatment of type II diabetes and/or obesity with associated insulin