Synthesis and biological activity of novel 5′-arylamino-nucleosides by microwave-assisted one-pot tandem Staudinger/aza-Wittig/reduction

Bioorganic & Medicinal Chemistry Letters
2011.0

Abstract

Novel pseudonucleosides with benzylamino group on 5'-position (4) were synthesized by using the microwave-assisted one-pot tandem Staudinger/aza-Wittig/reduction reaction in good yields of 55.2-71.7%. The deacetylation of 4 afforded compounds 5. HIV-1 reverse transcriptase (RT) inhibitory and antitumor activities were preliminarily evaluated with 5. The results showed that the new pseudonucleosides (5) could effectively inhibit HIV-1 RT activity, but no antitumor activity.

Knowledge Graph

Similar Paper

Synthesis and biological activity of novel 5′-arylamino-nucleosides by microwave-assisted one-pot tandem Staudinger/aza-Wittig/reduction
Bioorganic & Medicinal Chemistry Letters 2011.0
Synthesis of bi-/tricyclic azasugars fused thiazinan-4-one and their HIV-RT inhibitory activity
Bioorganic & Medicinal Chemistry Letters 2014.0
Synthesis of tetracyclic iminosugars fused benzo[e][1,3]thiazin-4-one and their HIV-RT inhibitory activity
Bioorganic & Medicinal Chemistry Letters 2016.0
Synthesis, antiviral activity, cytotoxicity and cellular pharmacology of l-3′-azido-2′,3′-dideoxypurine nucleosides
European Journal of Medicinal Chemistry 2011.0
The design and synthesis of N-1-alkylated-5-aminoaryalkylsubstituted-6-methyluracils as potential non-nucleoside HIV-1 RT inhibitors
Bioorganic & Medicinal Chemistry 2007.0
Synthesis of new (.+-.)-3,5-dihydroxypentyl nucleoside analogs from 1-amino-5-(benzyloxy)pentan-3-ol and their antiviral evaluation
Journal of Medicinal Chemistry 1990.0
Synthetic bicyclic iminosugar derivatives fused thiazolidin-4-one as new potential HIV-RT inhibitors
Bioorganic & Medicinal Chemistry Letters 2012.0
ArylH-Phosphonates 17: (N-Aryl)phosphoramidates of Pyrimidine Nucleoside Analogues and Their Synthesis, Selected Properties, and Anti-HIV Activity
Journal of Medicinal Chemistry 2011.0
Parallel Solution-Phase and Microwave-Assisted Synthesis of New S-DABO Derivatives Endowed with Subnanomolar Anti-HIV-1 Activity
Journal of Medicinal Chemistry 2005.0
Design and synthesis of N1-aryl-benzimidazoles 2-substituted as novel HIV-1 non-nucleoside reverse transcriptase inhibitors
Bioorganic & Medicinal Chemistry 2014.0