Synthesis of Modified C-Nucleosides of Therapeutic Significant: A Succinct Account

Nandagopal Hudait; Norein Sakander; Sanchari Kundu; Bisma Rasool; Jhimli Sengupta; Debaraj Mukherjee

doi:10.1055/a-2202-8808

Synlett, Table of Contents

Synlett 2024; 35(06): 635-648
DOI: 10.1055/a-2202-8808

account

Special Issue to Celebrate the Centenary Year of Prof. Har Gobind Khorana

Synthesis of Modified C-Nucleosides of Therapeutic Significant: A Succinct Account

Nandagopal Hudait

^aBose Institute, Department of Chemical Sciences, Unified Academic Campus, EN 80, Sector V, Bidhan Nagar, Kolkata, 700091, West Bengal, India

^bWest Bengal State University, Department of Chemistry, Berunanpukuria, North 24 Paraganas, Kolkata, 700126, West Bengal, India

,

Norein Sakander

^cNatural Products and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu, 180001, India

^dAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

,

Sanchari Kundu

^aBose Institute, Department of Chemical Sciences, Unified Academic Campus, EN 80, Sector V, Bidhan Nagar, Kolkata, 700091, West Bengal, India

,

Bisma Rasool

^cNatural Products and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu, 180001, India

^dAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

,

Jhimli Sengupta

^bWest Bengal State University, Department of Chemistry, Berunanpukuria, North 24 Paraganas, Kolkata, 700126, West Bengal, India

,

Debaraj Mukherjee∗

^aBose Institute, Department of Chemical Sciences, Unified Academic Campus, EN 80, Sector V, Bidhan Nagar, Kolkata, 700091, West Bengal, India

^dAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

› Author Affiliations

Abstract

All articles of this category

Abstract

Since their discovery in the 1950s, C-nucleosides have piqued the interest of both biologists and medicinal chemists. In this regard, C-nucleosides and their synthetic analogues have resulted in promising leads in drug design. Concurrently, advances in chemical syntheses have contributed to structural diversity and drug discovery efforts. Convergent and modular approaches to synthesis have gained much attention in this regard. Among them nucleophilic substitution at C-1 has seen wide applications, providing flexibility in synthesis, good yields, the ability to maneuver stereochemistry as well as to incorporate structural modifications. In this account, we briefly discuss the modular synthesis of C-nucleosides with a focus on mechanistic studies and sugar modifications that have resulted in potent lead molecules. Meanwhile, various FDA-approved C-nucleoside analogues have been reported previously for their antiviral and/or anticancer potential, with examples being pyrazomycin, remdesivir, pseudouridine, and pseudouridimycin.

1 Introduction and Motivation

2 Strategies for the Synthesis of C-Nucleosides

3 Biologically Active C-Nucleosides

4 Mechanistic Analysis of C-Nucleoside Formation

5 Synthesis and Manipulation of Medicinally Important C-Nucleoside Analogues

6 C-Nucleosides: Synthesis of C–C Bonds with a C-1′ Base

7 Conclusion

Key words

nucleosides - nucleobases - glycosylation - DNA - drugs - medicinal chemistry

Full Text

References

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