One-pot synthesis, characterization and antiviral properties of new benzenesulfonamide-based spirothiazolidinones

Apaydın Ç. B., Naesens L., Cihan Üstündağ G.

MOLECULAR DIVERSITY, vol.28, no.4, pp.2681-2688, 2024 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 28 Issue: 4
  • Publication Date: 2024
  • Doi Number: 10.1007/s11030-024-10912-x
  • Journal Name: MOLECULAR DIVERSITY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, BIOSIS, Chemical Abstracts Core, MEDLINE
  • Page Numbers: pp.2681-2688
  • Keywords: Antiviral activity, Influenza virus, Spirothiazolidinone, Sulfonamide, Synthesis
  • Istanbul University Affiliated: Yes

Abstract

A novel series of benzenesulfonamide substituted spirothiazolidinone derivatives (3a-j) were synthesized, characterized and evaluated for their antiviral activity. The spirocyclic compounds were prepared by the condensation of 4-(aminosulfonyl)-2-methoxybenzohydrazide, appropriate cyclic ketones and 2-mercaptopropionic acid in a one-pot reaction. The structures of the new compounds were established by IR, 1H NMR, 13C NMR (APT), and elemental analysis. The new compounds were evaluated in vitro antiviral activity against influenza A/H1N1, A/H3N2 and B viruses, as well as herpes simplex virus type 1 (HSV-1), respiratory syncytial virus (RSV) and yellow fever virus (YFV). Two derivatives bearing propyl (3d) and tert-butyl (3e) substituents at position 8 of the spiro ring exhibited activity against influenza A/H1N1 virus with EC50 values in the range of 35-45 mu M and no cytotoxicity at 100 mu M, the highest concentration tested.