52579-22-3

Usage

Chemical compound

6-fluoro-1-pentofuranosyl-1H-indole

Contains

Pentofuranosyl group
Indole ring with a fluoro substituent

Synthetic derivative of

Pentofuranosyl-1H-indole

Pentofuranosyl-1H-indole

Heterocyclic compound
Potential antineoplastic and antiviral activities

Addition of fluoro substituent

May alter biological activity
May enhance potential as a drug candidate

Pentofuranosyl group

Sugar-related moiety
May allow for improved pharmacokinetics and bioavailability

Further research and testing needed to determine

Specific pharmacological properties
Potential therapeutic applications for 6-fluoro-1-pentofuranosyl-1H-indole

Upstream product

• 882043-84-7 1-(2',3'-dideoxy-β-D-glycero-pent-2-enofuranosyl)-6-fluoroindole 
• 3093-97-8 6-fluoro-1H-indole-2-carboxylic acid 
• 459-57-4 4-fluorobenzaldehyde 
• 136818-43-4 methyl 6-fluoroindole-2-carboxylate 
• 399-51-9 6-fluoro-1H-indole 
• 882043-81-4 1-(2'-deoxy-5'-O-tert-butyldiphenylsilyl-3'-O-mesyl-β-D-erythro-pentofuranosyl)-6-fluoroindole 
• 943524-15-0 1-(2'-deoxy-5'-O-tert-butyldiphenylsilyl-β-D-erythro-pentofuranosyl)-6-fluoroindole 
• 882043-78-9 1-(2'-deoxy-β-D-erythro-pentofuranosyl)-6-fluoroindole 
• 882043-75-6 1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-6-fluoroindole 

Relevant academic research and scientific papers

Synthesis and structure of fluoroindole nucleosides

Chemically modified bases are frequently used to stabilize nucleic acids, to study the driving forces for nucleic acid structure formation, and to tune DNA and RNA hybridization conditions. Nucleoside analogues are chemical means to investigate hydrogen bonds, base stacking, and solvation as the three predominant forces that are responsible for the stability of nucleic acids. To obtain deeper insight into the contributions of these interactions to RNA stability, we decided to synthesize some novel nucleic acid analogues where the nucleobases are replaced by fluoroindoles. Fluorinated indoles can be compared with fluorinated benzimidazoles to determine the role of nitrogen in five-membered ring systems. The synthesis of fluoroindole ribonucleosides as well as the X-ray crystal structures of all synthesized fluoroindole ribonucleosides are reported here. These compounds could also be building blocks for a variety of biologically active RNA analogues.

Synthesis of fluorinated indoles as RNA analogues

Nucleoside analogues are chemical means to investigate hydrogen bonds, base stacking, and solvation as the three predominant forces that are responsible for the stability of secondary structure of nucleic acids. To obtain deeper insight into the contributions of these interactions to RNA stability apart from the ones exerted by the predominant nucleosides we decided to synthesize some novel nucleic acid analogues where the nucleobases are replaced by fluoroindoles. Fluorinated indoles can be compared to fluorinated benzimidazoles to determine the role of nitrogen in five membered ring system. The synthesis of fluoroindole ribonucleosides is described here. Copyright Taylor & Francis Group, LLC.