New Sulphonamide and Carboxamide Derivatives of Acyclic C-Nucleosides of Triazolo-Thiadiazole and the Thiadiazine Analogues. Synthesis, Anti-HIV, and Antitumor Activities. Part 2

Abstract

A new series of acyclic C-nucleosides 1′,2′-O-isopropylidene-D-ribo-tetritol-1-yl)[1,2,4] triazolo[3,4-b][1,3,4]thiadiazoles bearing arylsulfonamide (5–8) and arylcarboxamide (9–12) residues have been synthesized under microwave irradiation. Thiadiazines 13–15 have been analogously prepared, and upon acid hydrolysis, afforded the free nucleosides 16–18. The new synthesized compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. Compound 7 was also screened against a panel of tumor cell lines consisting of CD4 human T-cells.

Keywords:

• anti-HIV activity
• acyclic C-nucleosides
• microwave-assisted synthesis
• triazolo-thiadiazoles and -thiadiazines
• sulphonamides
• carboxamides

Acknowledgments

We thank Professor E. De Clercq and Professor C. Pannecouque of Rega Institute of Medical Research, Katholieke Universiteit, Leuven (Belgium) for the anti-HIV screening. Miss Firemel of Konstanz University (Germany) is gratefully acknowledged for the two-dimensional NMR experiments. We are grateful for Professor P. La Colla and Dr. R. Loddo of Cagliari University (Italy) for the antitumor screening. Mr. Galtesky of Konstanz University (Germany) is gratefully acknowledged for the 2D-NMR experiments and mass measurements, respectively.