Synthesis and Anticancer Activities of Amide-Bridged Coumarin-Quinazolinone Hybrid Compounds

Çalişkan N., Menteşe E., Yılmaz F., Ilhan M. S.

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, cilt.60, sa.5, ss.918-926, 2024 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 60 Sayı: 5
  • Basım Tarihi: 2024
  • Doi Numarası: 10.1134/s1070428024050142
  • Dergi Adı: RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core
  • Sayfa Sayıları: ss.918-926
  • Anahtar Kelimeler: anticancer, cytotoxicity, PC-3, MCF-7 coumarin, quinazolinone
  • Recep Tayyip Erdoğan Üniversitesi Adresli: Evet

Özet

Abstract: Some novel 3-aminoquinazolin-4(3H)-one derivatives were synthesized by the reaction of 2-aminobenzhydrazide and corresponding iminoester hydrochlorides and then reacted with coumarin-3-carbonyl chloride to obtain novel coumarin–quinazolinone hybrids. The synthesized hybrid compounds were screened for their anticancer activity against various human cancer and normal cell lines. N-{2-[(4-Bromo- and N-{2-[(3-bromo-phenyl)methyl]-4-oxoquinazolin-3(4H)-yl}-2-oxo-2H-1-benzopyran-3-carboxamides exhibited the highest cytotoxic effect on the PC-3 prostate cancer cell line: IC50 35.3 ± 0.6 and 36.8 ± 0.8 µg/L, respectively. N-{2-[(4-Fluoro-, N-{2-[(4-bromo-, and N-{2-[(3,4-dichloro-phenyl)methyl]-4-oxoquinazolin-3(4H)-yl}-2-oxo-2H-1-benzopyran-3-carboxamides showed the highest activity against the MCF-7 breast cancer cell line: IC50 48.5 ± 0.4, 44.8 ± 0.4 and 46.1 ± 0.5 µg/L, respectively.