Synthesis, structure and in vitro cytotoxicity testing of some 2‐aroylbenzofuran‐3‐ols

• Published in: Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2020-09, Vol.76 (9), p.874-882
• Main Authors: Cong, Nguyen Tien, Trang, Huynh Thi Xuan, Dung, Pham Duc, Phuong, Tran Hoang, Trung, Vu Quoc, Dat, Nguyen Dang, Anh, Dang Thi Tuyet, Tuyen, Nguyen Van, Van Meervelt, Luc
• Format: Article
• Language: English
• Subjects: 2‐aroylbenzofuran‐3‐ol; bromosalicylate; crystal structure; Cytotoxicity; iodosalicylate; Mass spectrometry; NMR spectroscopy; Salicylic acid; Toxicity testing
• ISSN: 2053-2296; 0108-2701; 2053-2296; 1600-5759
• DOI: 10.1107/S2053229620011018

Five 2‐aroyl‐5‐bromobenzo[b]furan‐3‐ol compounds (two of which are new) and four new 2‐aroyl‐5‐iodobenzo[b]furan‐3‐ol compounds were synthesized starting from salicylic acid. The compounds were characterized by mass spectrometry and 1H NMR and 13C NMR spectroscopy. Single‐crystal X‐ray diffraction studies of four compounds, namely, (5‐bromo‐3‐hydroxybenzofuran‐2‐yl)(4‐fluorophenyl)methanone, C15H8BrFO3, (5‐bromo‐3‐hydroxybenzofuran‐2‐yl)(4‐chlorophenyl)methanone, C15H8BrClO3, (5‐bromo‐3‐hydroxybenzofuran‐2‐yl)(4‐bromophenyl)methanone, C15H8Br2O3, and (4‐bromophenyl)(3‐hydroxy‐5‐iodobenzofuran‐2‐yl)methanone, C15H8BrIO3, were also carried out. The compounds were tested for their in vitro cytotoxicity on the four human cancer cell lines KB, Hep‐G2, Lu‐1 and MCF7. Six compounds show good inhibiting abilities on Hep‐G2 cells, with IC50 values of 1.39–8.03 µM. Nine 2‐aroyl‐5‐bromo/iodobenzofuran‐3‐ol compounds were synthesized, of which four were further characterized by single‐crystal X‐ray diffraction. Six compounds show promising in vitro cytotoxicity on four human cancer cell lines.