Spirooxindole 5‐(Trifluoromethyl)benzothiazole Hybrids: Synthesis, Crystal Structure, and Antioxidant Activity

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Karabağ N., Temizer Keser A. B., Pekmez M., Mertoğlu Kamalı E., Kaynak F. B., Özsoy N., ...Daha Fazla

ARCHIV DER PHARMAZIE, cilt.359, sa.e70343, ss.1-17, 2026 (SCI-Expanded, Scopus)

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 359 Sayı: e70343
  • Basım Tarihi: 2026
  • Doi Numarası: 10.1002/ardp.70343
  • Dergi Adı: ARCHIV DER PHARMAZIE
  • Derginin Tarandığı İndeksler: Health Research Premium Collection (ProQuest), Scopus, Pharma Collection (ProQuest), Science Citation Index Expanded (SCI-EXPANDED), BIOSIS, Chemical Abstracts Core, Chimica, EMBASE, MEDLINE
  • Sayfa Sayıları: ss.1-17
  • Açık Arşiv Koleksiyonu: AVESİS Açık Erişim Koleksiyonu
  • İstanbul Üniversitesi-Cerrahpaşa Adresli: Evet

Özet

Antioxidants neutralize free radicals to reduce oxidative stress and cellular damage, preventing various chronic diseases. In thisstudy, the antioxidant activities of novel 5‐(trifluoromethyl)‐3H‐spiro[1,3‐benzothiazole‐2,3′‐indol]‐2′(1′H)‐ones (4a–h), alongwith the spirocyclic 2‐indolinones (4i–m and 5a–n) previously synthesized by our group, were investigated for the first time, tofind a multi‐modal antioxidant and to understand the impact of the trifluoromethyl group located at the 5‐position of thebenzothiazole on antioxidant activity. For this purpose, the 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH•) free radical scavenging,superoxide anion scavenging, ABTS•+ radical cation scavenging, trolox equivalent antioxidant capacity, ferric ion reductionantioxidant potential (FRAP), and lipid peroxidation (TBARs) assays were carried out. The cytotoxic effects of compounds(4g, 4h, 4i, 4j, 4l, 5a, 5b, and 5h), which showed promising in vitro antioxidant activity in at least two in vitro tests, wereinvestigated in healthy human fibroblast (HFF‐1) cells. The effects of non‐toxic doses of these compounds on intracellularreactive oxygen species were also evaluated. As a result, it was determined that compound 4l (R1 = 5‐F and R2 = H) exhibitedgreater radical scavenging activity than the other compounds tested. The IC50 of compound 4l was 74.13 µM while compound4g (R1 = 5‐Cl‐7‐CH3 and R2 = H) was non‐toxic (IC50 > 200 μM). Compounds 4e (R1 = 5‐Cl and R2 = H) and 4f (R1 = 7‐Br andR2 = H), exhibited higher lipid peroxidation inhibitory activity than α‐tocopherol in vitro; however, the difference was notstatistically significant.