2862-16-0

Usage

Uses

Used in Pharmaceutical Industry:
7-deazainosine is used as a potential anti-cancer agent for its ability to inhibit cell growth and induce apoptosis in cancer cells. Its unique properties make it a promising candidate for the development of novel therapeutics targeting various types of cancer.
Used in Basic Biology Research:
7-deazainosine is used as a key molecule in understanding the biosynthesis of queuosine and its role in maintaining the proper structure and function of tRNA molecules. Studying 7-deazainosine helps researchers gain insights into the accurate translation of the genetic code during protein synthesis, which is fundamental to various biological processes.
Used in Drug Development:
7-deazainosine is used as a starting point for the development of new drugs targeting cancer cells. Its ability to inhibit cell growth and induce apoptosis makes it a valuable compound for designing and synthesizing novel anti-cancer therapeutics with improved efficacy and reduced side effects.

InChI:InChI=1/C11H13N3O5/c15-3-6-7(16)8(17)11(19-6)14-2-1-5-9(14)12-4-13-10(5)18/h1-2,4,6-8,11,15-17H,3H2,(H,12,13,18)/t6-,7-,8-,11-/m1/s1

Upstream product

• 426823-20-3 4-methoxy-5-iodo-N7-(β-D–ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 29914-75-8 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 69-33-0 tubercidin 
• 76567-71-0 2-Methylthio-7-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-4H-pyrrolo<2,3-d>pyrimidin-4-on 
• 76567-69-6 4-Methoxy-2-methylthio-7-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidin 
• 123148-78-7 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine 
• 480439-89-2 4-chloro-5-iodo-7-[(2,3,5-tri-O-benzoyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 76567-72-1 7-(2,3,5-Tri-O-benzyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidin-4(3H)-on 
• 16754-81-7 4-methoxy-7-(β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 

Relevant academic research and scientific papers

C6–O-alkylated 7-deazainosine nucleoside analogues: Discovery of potent and selective anti-sleeping sickness agents

African trypanosomiasis, a deadly infectious disease caused by the protozoan Trypanosoma brucei spp., is spread to new hosts by bites of infected tsetse flies. Currently approved therapies all have their specific drawbacks, prompting a search for novel th

7-Deazainosine derivatives: Synthesis and characterization of 7- and 7,8-substituted pyrrolo [2,3-d]pyrimidine ribonucleosides

The synthesis of model 7 deazapurine derivatives related to tubercidin and toyocamycin has been performed. Tubercidin derivatives were obtained by simple conversion of the amino group of the heterocyclic moiety of the starting 7-deazadenosine compounds, into a hydroxyl group. Preparation of toyocamycin derivatives was accomplished by treatment of the silylated 6-bromo-5- cyanopyrrolo[2,3-d]pyrimidin-4-one with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d- ribofuranose. The glycosylation reaction afforded a mixture of 8-bromo 7-cyano 2′,3′,5′ tri-O-benzoyl 7-deazainosine and 6-bromo-5-cyano-3- (2′,3′,5′-tri-O-benzoyl-β-d-ribofuranosyl)pyrrolo[2,3-d] -pyrimidin-4-one isomers: The structures were assigned on the basis of NMR spectroscopy studies. Next deprotection treatment gave the novel 7-deazainosine ribonucleosides. Copyright Taylor & Francis Group, LLC.

7-Functionalized 7-deazapurine β-d and β-l-ribonucleosides related to tubercidin and 7-deazainosine: glycosylation of pyrrolo[2,3-d]pyrimidines with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d or β-l-ribofuranose

Several 7-functionalized 7-deazapurine ribonucleosides were prepared. Glycosylation of 7-halogenated 6-chloro-7-deazapurines with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose or 1-O-acetyl-2,3,5-tri-O-benzoyl-β-l-ribofuranose gave the protected β-d-nuc

Structural determinants for N1/N7 cyclization of nicotinamide hypoxanthine 5′-dinucleotide (NHD+) derivatives by ADP-ribosyl cyclase from Aplysia californica: Ca2+-mobilizing activity of 8-substituted cyclic inosine 5′-diphosphoribose analogues in T-lymphocytes

A series of nicotinamide hypoxanthine 5′-dinucleotide (NHD +) analogues modified at C-8 (2-5) and 7-deaza-NHD+ were synthesized, and cyclization in the presence of Aplysia ADP-ribosyl cyclase was studied. All 8-substituted NHD+ analogues were converted into their N1-cyclic forms by the enzyme, while in contrast, 7-deaza-NHD+ 17 was hydrolyzed into 7-deazainosine 5′-diphosphoribose (7-deaza-IDPR) 25. Correlations are made showing that the conformation of the NHD+ substrate is the key to successful cyclization. The pharmacological activities of these novel cIDPR derivatives were evaluated in both permeabilized and intact Jurkat T-lymphocytes. The results show that in permeabilized cells both 8-iodo 1g and 8-N3-N1-cIDPR 1d have an activity comparable to that of cADPR, while 8-iodo 1g and 8-phenyl-N1-cIDPR 1c have a small but significant effect in intact cells and can therefore be regarded as membrane-permeant; thus, cIDPR derivatives are emerging as important novel biological tools to study cADPR-mediated Ca2+ release in T-cells.