Synthesis and antiviral properties of novel indole-based thiosemicarbazides and 4-thiazolidinones

Cihan-Ustundag G., Gursoy E., NAESENS L., Ulusoy-Guzeldemirci N., Capan G.

BIOORGANIC & MEDICINAL CHEMISTRY, cilt.24, sa.2, ss.240-246, 2016 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 24 Sayı: 2
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1016/j.bmc.2015.12.008
  • Dergi Adı: BIOORGANIC & MEDICINAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.240-246
  • Anahtar Kelimeler: Indole, Thiosemicarbazide, 4-Thiazolidinone, Antiviral activity, Coxsackie B4 virus, IN-VITRO, COXSACKIE-VIRUS, DERIVATIVES, INHIBITION, ARBIDOL
  • İstanbul Üniversitesi Adresli: Evet

Özet

A novel series of indolylthiosemicarbazides (6a-6g) and their cyclization products, 4-thiazolidinones (7a-7g), have been designed, synthesized and evaluated, in vitro, for their antiviral activity against a wide range of DNA and RNA viruses. Compounds 6a, 6b, 6c and 6d exhibited notable antiviral activity against Coxsackie B4 virus, at EC50 values ranging from 0.4 to 2.1 mu g/mL. The selectivity index (ratio of cytotoxic to antivirally effective concentration) values of these compounds were between 9 and 56. Besides, 6b, 6c and 6d also inhibited the replication of two other RNA viruses, Sindbis virus and respiratory syncytial virus, although these EC50 values were higher compared to those noted for Coxsackie B4 virus. The SAR analysis indicated that keeping the free thiosemicarbazide moiety is crucial to obtain this antiviral activity, since the cyclization products (7a-7g) did not produce any antiviral effect. (c) 2015 Elsevier Ltd. All rights reserved.