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

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

MOLECULAR DIVERSITY, cilt.28, sa.4, ss.2681-2688, 2024 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 28 Sayı: 4
  • Basım Tarihi: 2024
  • Doi Numarası: 10.1007/s11030-024-10912-x
  • Dergi Adı: MOLECULAR DIVERSITY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, BIOSIS, Chemical Abstracts Core, MEDLINE
  • Sayfa Sayıları: ss.2681-2688
  • Anahtar Kelimeler: Antiviral activity, Influenza virus, Spirothiazolidinone, Sulfonamide, Synthesis
  • İstanbul Üniversitesi Adresli: Evet

Özet

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.