28152-41-2

Usage

Chemical structure

A pentofuranosyl group attached to a 1H-indazole moiety.

Type of compound

Indazole derivative.

Formation

Formed by replacing one of the hydrogen atoms on the indazole ring with the pentofuranosyl group.

Potential applications

Pharmaceutical applications due to the indazole moiety, which is a common component in many bioactive compounds.

Biological activities

The presence of the pentofuranosyl group may impart additional biological activities.

Pharmacokinetic properties

The pentofuranosyl group may improve the compound's pharmacokinetic properties.

Further research

Necessary to fully understand the potential uses and properties of 1-pentofuranosyl-1H-indazole.

Upstream product

• 52562-51-3 1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)indazole 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 271-44-3 benzimidazole 

Relevant academic research and scientific papers

Transglycosylation of β-D-ribofuranosylindazoles

Irreversible, acid-catalyzed 2 → 1 transglycosylation reactions of fully acetylated β-D-ribofuranosylindazoles were studied applying HPLC analysis. Results so obtained support the intermolecular mechanism of transglycosylation via a 1,2-diglycosylindazole intermediate and are compared to those of the purine series.

Synthesis and enzymatic activity of some new purine ring system analogues of adenosine 3',5'-cyclic monophosphate

A series of novel adenosine 3',5'-cyclic monophosphate (cAMP) analogues, as well as their 6-deamino and 6-nitro derivatives, were synthesized where the purine ring was replaced by indazole, benzotriazole, and benzimidazole. The 3',5'-cyclic monophosphates of indazole and benzotriazole ribofuranosides, where the sugar-phosphate moiety is attached to the N-2 nitrogen atoms of the heterocycles, were also prepared. The biological efficiency of the analogues was tested by their ability to activate purified cAMP-dependent protein kinase I (PK-I) from rabbit skeletal muscle and cAMP- dependent protein kinase II (PK-II) from bovine heart. Each cyclic nucleotide is capable of activating both PK isozymes in half-maximum concentrations (K(a)) ranging from 2.0 · 10-8 to 4.8 · 10-6 M. The cyclic phosphate of N-1-β-D-ribofuranosylindazole (13) proved to be a very poor activator for both PK-I and PK-II, but when indazole binds by N-2 to ribose or when the hydrogen atom at C-4 is substituted by a nitro or amino group, activities of the analogues increase considerably. The activating potencies of benzotriazole derivatives are similar to that of cAMP, irrespective of the C- 4 substituents. The K(a)' values of cyclic nucleotides containing benzimidazole were found to be higher for PK-II than for PK-I; e.g. the activity of 4-nitro-1-β-D-ribofuranosylbenzimidazole 3',5'-cyclic monophosphate (32) is nearly 20 times as high for PK-II than for PK-I.