Synthesis and Anti‐HIV Activity of Triazolo‐Fused 3′,5′‐Cyclic Nucleoside Analogues Derived from an Intramolecular <i>Huisgen</i> 1,3‐Dipolar Cycloaddition

Sun, Jingbo; Liu, Xinyu; Li, Hongming; Duan, Ronghui; Wu, Jianjun

doi:10.1002/hlca.201100366

Cited by 11 publications

(3 citation statements)

References 48 publications

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“…The synthesized compounds were tested for exploring the anti-HIV activity and in a H9 T lymphocytes assay for measuring the cell toxicity with modest results. 16 TSAO nucleoside analogues represent a class of HIV-1-specific agents, the prototype compound of which is the 1-[2',5'-bis-O-(tert-butyldimethylsilyl)--D-ribofuranosyl-thymine]-3'-spiro-5"-(4"-amino-1",2"-oxathiole-2",2"-dioxide (TSAO-T, 6). They are targeted at the HIV-1-encoded RT with which they interact at a nonsubstrate binding site; they are not antivirally effective against HIV-2 and other (retro)viruses.…”

Section: Nhmentioning

confidence: 99%

Synthesis and biological activity of potential antiviral compounds through 1,3-dipolar cycloadditions; Part 1: general aspects and reactions of azides

Quadrelli¹,

Faita²,

Leusciatti³

2022

Arkivoc

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Prominent in the current stage of drug development, antiviral compounds can be efficiently prepared through cycloaddition reactions. This review reports the use of 1,3-dipolar cycloaddition reactions of selected 1,3dipoles, in particular azides, in the light of their application for the preparation of key intermediates in the design and synthesis of compounds that were tested for their antiviral activities against a variety of viruses. The products obtained from these pericyclic reaction approaches were tested for their activities in terms of blocking the virus replication and the relevant biological data are highlighted.

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Section: Nhmentioning

confidence: 99%

Synthesis and biological activity of potential antiviral compounds through 1,3-dipolar cycloadditions; Part 1: general aspects and reactions of azides

Quadrelli¹,

Faita²,

Leusciatti³

2022

Arkivoc

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“…Thus, synthesis of cyclic dinucleotide analogues is a challenging yet exciting field of research and has the potential to revolutionize drug development. Wu and co‐workers reported the synthesis of triazolo‐fused 3’,5’‐cyclic nucleoside analogues I (Figure ) by an intramolecular 1,3‐dipolar cycloaddition of nucleoside‐derived azido‐alkynes . It was observed that these compounds exhibited anti‐HIV activity and cell toxicity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti‐Proliferative Activity of a Triazole‐Fused Thymidine Analogue

et al. 2020

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Here we report the synthesis of two-an acyclic and a macrocyclic-analogues of thymidine linked to a triazole moiety. The new molecules were synthesized through an intramolecular 1,3-dipolar cycloaddition reaction of the diazido derivative of thymidine with a suitable alkyne. The acyclic nucleoside showed dose dependent cytotoxicity against glioblastoma and breast cancer cells by causing significant cellular damage as studied with confocal laser scanning microscopy. In silico induced fit molecular docking studies showed poly(ADP-ribose) polymerase 1 (PARP1) as a potential target of the acyclic nucleoside. On the other hand, both the analogues showed no toxicity against normal fibroblast cells. ChemistrySelectCommunications

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“…The Huisgen 1,3‐dipolar cycloaddition between azide and alkyne leading to 1,5‐substitued triazole moiety has gained considerable attention due to its vast biological applications . Notably, several members of the 1,2,3‐triazole family have shown gripping biological properties, and the triazole moiety with its novel structural features and physiochemical properties is regarded as a privileged structure in drug design and discovery (Figure , 1–4 ) . When customized nucleosides possessing alkyne and azide moieties disposed in the same nucleosides are heated, they undergo intramolecular Huisgen cycloaddition to furnish 1,5‐disubstituted triazole compounds.…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Synthesis of C‐4′‐(1,5‐disubstituted)‐triazole‐spiro‐α‐L‐arabinofuranosyl Nucleosides

et al. 2017

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The synthesis of C‐4′‐(1,5‐disubstituted)‐triazole‐spiro‐α‐L‐arabinofuranosyl nucleosides has been achieved in a regio‐ and stereospecific manner by using intramolecular Huisgen 1,3‐dipolar cycloaddition reaction. The synthesis of these nucleosides necessitates the possession of azide and alkyne moieties in the same molecule, which is being employed as the precursor. Thus, the crucial step in the synthesis of targeted compound is the preparation of 1,2,3‐tri‐O‐acetyl‐5‐azido‐5‐deoxy‐4‐C‐propynyl‐α,β‐L‐arabinofuranose and its conversion to corresponding nucleosides via nucleobase coupling. The microwave heating of such tailor made nucleoside precursors furnishes the targeted spironucleosides, which combines conformational‐restriction concept with a triazole structural feature highly sought in drug design.

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Synthesis and Anti‐HIV Activity of Triazolo‐Fused 3′,5′‐Cyclic Nucleoside Analogues Derived from an Intramolecular Huisgen 1,3‐Dipolar Cycloaddition

Cited by 11 publications

References 48 publications

Synthesis and biological activity of potential antiviral compounds through 1,3-dipolar cycloadditions; Part 1: general aspects and reactions of azides

Synthesis and biological activity of potential antiviral compounds through 1,3-dipolar cycloadditions; Part 1: general aspects and reactions of azides

Synthesis and Anti‐Proliferative Activity of a Triazole‐Fused Thymidine Analogue

Microwave‐Assisted Synthesis of C‐4′‐(1,5‐disubstituted)‐triazole‐spiro‐α‐L‐arabinofuranosyl Nucleosides

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