55627-73-1

Usage

Uses

Used in Pharmaceutical Industry:
8-BROMOINOSINE is used as a synthetic precursor for the preparation of (bromo)adenosine and (bromo)guanosine derivatives. These derivatives are essential in the development of new drugs and therapies, particularly in the treatment of various diseases and conditions.
Used in Chemical Synthesis:
8-BROMOINOSINE is used as a reagent/reactant in the preparation of purine-substituted methylglucosamines. This application is crucial for the development of new compounds with potential immunostimulating activity, which can be beneficial in the field of medicine and healthcare.
Used in Microwave-Mediated Synthesis:
8-BROMOINOSINE is employed in microwave-mediated regioselective and chemoselective bromination of adenosine, inosine, and guanosine derivatives. This method allows for efficient and targeted synthesis of specific compounds, which can be advantageous in various research and development applications.

InChI:InChI=1/C10H11BrN4O5/c11-10-14-4-7(12-2-13-8(4)19)15(10)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H,12,13,19)

Upstream product

• 2946-39-6 8-bromoadenosine 
• 55627-72-0 2’,3’,5’-tri-O-acetyl-8-bromoinosine 
• 87515-42-2 8-benzylaminoinosine 
• 121637-32-9 8-(4-morpholinyl)inosine 
• 58-61-7 adenosine 

Downstream Products

• 87515-50-2 C₂₀H₂₁N₅O₄ 
• 87515-42-2 8-benzylaminoinosine 
• 87515-46-6 8-benzylamino-2',3'-O-isopropylideneinosine 
• 27883-25-6 8-mercaptoinosine 

Relevant academic research and scientific papers

The supramolecular helical architecture of 8-oxoinosine and 8-oxoguanosine derivatives

The 8-oxoguanosine derivative 1 and the 8-oxoinosine derivative 2b, with appropriate substituents on their ribose moieties, form hexagonal lyotropic mesophases in hydrocarbon solvents. Small-angle X-ray scattering analysis of a film of 1 and of the mesophase of 2b, and NMR and CD spectra of isotropic solutions of 2b, indicate that in both cases the supramolecular structures adopted are continuous helices formed by a hydrogen-bond network between the heterocyclic bases. Notably, while derivative 2b, which bears large substituents on its ribose moiety, undergoes self-assembly and mesophase formation, oxoinosine 2a, with only decanoyl groups on its ribose moiety, does not. This may be ascribed to the reduced amphiphilic properties of the latter and the absence of aromatic groups.

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.

Anti-HCV nucleoside derivatives

The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.