Fluorinated Nucleosides: Synthesis, Modulation in Conformation and Therapeutic Application.

Shantanu Pal, Girish Chandra, Samridhi Patel, Sakshi Singh

Journal: Chemical record (New York, N.Y.) 2022;22(5):e202100335

PMID: 35253973

Abstract

Over the last twenty years, fluorination on nucleoside has established itself as the most promising tool to use to get biologically active compounds that could sustain the clinical trial by affecting the pharmacodynamics and pharmacokinetic properties. Due to fluorine's inherent unique properties and its judicious introduction into the molecule, makes the corresponding nucleoside metabolically very stable, lipophilic, and opens a new site of intermolecular binding. Fluorination on various nucleosides has been extensively studied as a result, a series of fluorinated nucleosides come up for different therapeutic uses which are either approved by the FDA or under the advanced stage of the clinical trial. Here in this review, we are summarizing the latest development in the chemistry of fluorination on nucleoside that led to varieties of new analogs like carbocyclic, acyclic, and conformationally biased nucleoside and their biological properties, the influence of fluorine on conformation, oligonucleotide stability, and their use in therapeutics.

© 2022 The Chemical Society of Japan & Wiley-VCH GmbH.

Address: School of Basic Sciences, Indian Institute of Technology, Bhubaneswar Argul, Odisha, India, 752050.; Department of Chemistry, School of Physical and Chemical Sciences, Central University of South Bihar, SH-7, Gaya Panchanpur Road, Gaya, Bihar, India, 824236.

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