Affordable Access

deepdyve-link
Publisher Website

An efficient synthesis tetrazole and oxadiazole analogues of novel 2′-deoxy-C-nucleosides and their antitumor activity

Authors
  • Penjarla, Srishylam1, 2
  • Kumar Sabui, Subir1
  • Sudhakar Reddy, Dhande1
  • Banerjee, Shyamapada1
  • Yella Reddy, Paidi1
  • Penta, Santhosh2
  • Sanghvi, Yogesh S.1, 3
  • 1 Sapala Organics Pvt. Ltd, Plot Nos. 146B & 147 IDA Mallapur, Phase-II, Hyderabad 500076, Telangana, India
  • 2 Department of Chemistry, National Institute of Technology Raipur, G.E. Road, Raipur, Chhattisgarh 492010, India
  • 3 Rasayan Inc., 2802 Crystal Ridge Road, Encinitas, CA 92024-6615, USA
Type
Published Article
Journal
Bioorganic & medicinal chemistry letters
Publication Date
Oct 21, 2020
Volume
30
Issue
24
Pages
127612–127612
Identifiers
DOI: 10.1016/j.bmcl.2020.127612
PMID: 33098969
PMCID: PMC7576186
Source
PubMed Central
Keywords
Disciplines
  • Article
License
Unknown

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.

Report this publication

Statistics

Seen <100 times