1. An efficient synthesis tetrazole and oxadiazole analogues of novel 2'-deoxy-C-nucleosides and their antitumor activity.
- Author
-
Penjarla S, Kumar Sabui S, Sudhakar Reddy D, Banerjee S, Yella Reddy P, Penta S, and Sanghvi YS
- Subjects
- Antineoplastic Agents chemical synthesis, Antineoplastic Agents pharmacology, Cell Line, Tumor, Chemistry Techniques, Synthetic economics, Chemistry Techniques, Synthetic methods, Humans, Neoplasms drug therapy, Nucleosides chemical synthesis, Nucleosides pharmacology, Oxadiazoles chemical synthesis, Oxadiazoles pharmacology, Stereoisomerism, Tetrazoles chemical synthesis, Tetrazoles pharmacology, Antineoplastic Agents chemistry, Nucleosides analogs & derivatives, Oxadiazoles chemistry, Tetrazoles chemistry
- Abstract
Various tetrazole and oxadiazole C-nucleoside analogues were synthesized starting from pure α- or β-glycosyl-cyanide. The synthesis of glycosyl-cyanide as key precursor was optimized on gram-scale to furnish crystalline starting material for the assembly of C-nucleosides. Oxadizole C-nucleosides were synthesized via two independent routes. First, the glycosyl-cyanide was converted into an amidoxime which upon ring closure offered an alternative pathway for the assembly of 1,2,4-oxadizoles in an efficient manner. Second, both anomers of glycosyl-cyanide were transformed into tetrazole nucleosides followed by acylative rearrangement to furnish 1,3,4-oxadiazoles in high yields. These protocols offer an easy access to otherwise difficult to synthesize C-nucleosides in good yield and protecting group compatibility. These C-nucleosides were evaluated for their antitumor activity. This work paves a path for facile assembly of library of new chemical entities useful for drug discovery., (Copyright © 2020 Elsevier Ltd. All rights reserved.)
- Published
- 2020
- Full Text
- View/download PDF