Novel 1'-homo-N-2'-deoxy-α-nucleosides: synthesis, characterization and biological activity.
Alejandro CarneroVirginia Martín-NievesYogesh S SanghviOlivia O RusselLeda BassitRaymond F SchinaziSusana FernándezMiguel FerreroPublished in: RSC advances (2020)
For the first time, a series of novel 1'-homo-N-2'-deoxy-α-nucleosides containing natural nucleobases as well as 5-fluoro and 5-iodopyrimidine analogs have been synthesized in an efficient manner. Additionally, a high yield protocol for the assembly of a dimeric scaffold containing two sugar moieties linked to the N-1 and N-3 positions of a single pyrimidine base has been accomplished. The structures of the novel homonucleosides were established by a single crystal X-ray structure of 1'-homo-N-2'-deoxy-α-adenosine and NMR studies. The biological activity of these 1'-homo-N-2'-deoxy-α-nucleosides as antiviral (HIV-1 and HBV) and cytotoxic studies was measured in multiple cell systems. The unique structure and easy accessibility of these compounds may allow their use in the design of new nucleoside analogs with potential biological activity and as a scaffold for combinatorial chemistry.
Keyphrases
- high resolution
- case control
- hepatitis b virus
- human immunodeficiency virus
- antiretroviral therapy
- hiv infected
- molecular docking
- hepatitis c virus
- randomized controlled trial
- magnetic resonance
- hiv positive
- tissue engineering
- single cell
- hiv testing
- hiv aids
- positron emission tomography
- risk assessment
- men who have sex with men
- liver failure
- mass spectrometry
- climate change
- south africa
- drug discovery
- molecular dynamics simulations