Synthesis, structural characterization and biological evaluation of 4′-C-methyl- and phenyl-dioxolane pyrimidine and purine nucleosides
| Autor: | Lak Shin Jeong, Andrea Cornia, Silvia Franchini, Silvia Madeddu, Annalisa Tait, Roberta Loddo, Sang Kook Lee, Giuseppina Sanna, Jayoung Song, Claudia Sorbi, Umberto Maria Battisti, Livio Brasili |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Models
Molecular 0301 basic medicine Purine Anomer Pyrimidine Anti-HIV Agents Stereochemistry Pharmaceutical Science Antineoplastic Agents Microbial Sensitivity Tests Crystallography X-Ray Cell Line Structure-Activity Relationship 03 medical and health sciences chemistry.chemical_compound Drug Discovery Humans Antiviral Purine metabolism Cell Proliferation 1 3-Dioxolanes Antitumor Nucleosides Purines Pyrimidines Vorbrüggen reaction Organic Chemistry Dose-Response Relationship Drug Molecular Structure Dioxolanes Biological activity Purine Nucleosides Pyrimidine Nucleosides Antimicrobial 030104 developmental biology chemistry Dioxolane HIV-1 Molecular Medicine Drug Screening Assays Antitumor 3-Dioxolanes Nucleoside |
| Zdroj: | Archives of Pharmacal Research. 40:537-549 |
| ISSN: | 1976-3786 0253-6269 |
| DOI: | 10.1007/s12272-016-0825-6 |
| Popis: | Nucleoside analogues play an important role in antiviral, antibacterial and antineoplastic chemotherapy. Herein we report the synthesis, structural characterization and biological activity of some 4′-C -methyl- and -phenyl dioxolane-based nucleosides. In particular, α and β anomers of all natural nucleosides were obtained and characterized by NMR, HR-MS and X-ray crystallography. The compounds were tested for antimicrobial activity against some representative human pathogenic fungi, bacteria and viruses. Antitumor activity was evaluated in a large variety of human cancer cell-lines. Although most of the compounds showed non-significant activity, 23α weakly inhibited HIV-1 multiplication. Moreover, 22α and 32α demonstrated a residual antineoplastic activity, interestingly linked to the unnatural α configuration. These results may provide structural insights for the design of active antiviral and antitumor agents. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full text from SpringerLink