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Synthesis and Cytotoxic Evaluation of Potential Bis‐Intercalators: Tetramethylenebis(oxy)‐ and Hexamethylenebis(oxy)‐Linked Assemblies Consisting of Flavone, Xanthone, Anthraquinone, and Dibenzofuran
Author(s) -
Wang TaiChi,
Zhao YueLing,
Liou ShorongShii
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200205)85:5<1382::aid-hlca1382>3.0.co;2-y
Subject(s) - chemistry , cytotoxicity , stereochemistry , intercalation (chemistry) , cytotoxic t cell , dibenzofuran , combinatorial chemistry , organic chemistry , biochemistry , in vitro
Abstract In a search for potential inhibitors of solid‐tumor growth, certain alkanediylbis(oxy)‐linked assemblies were synthesized and evaluated for their cytotoxicity as bis‐intercalators. Symmetrical assemblies 1b – 12b were synthesized from their respective Aryl‐OH and either dibromobutane or dibromohexane, while unsymmetrical ones 13 – 15 were prepared from Aryl 1 ‐OH and either Aryl 2 ‐O‐(CH 2 ) 4 Br or Aryl 2 ‐O‐(CH 2 ) 6 Br. These bis‐intercalators were inactive against the growth of leukemia cells. However, some of them were active against the growth of certain solid tumors such as HOP‐62, HOP‐92 (non‐small‐cell lung cancer), SF‐265, SNB‐75, U251 (CNS cancer), A498 (renal cancer), and HS578T (breast cancer). Among them, [hexane‐1,6‐diylbis(oxy)bis(4,1‐phenylene)]bis[4 H ‐1‐benzopyran] ( 6b ) was especially active against the growth of all CNS cancer cell lines and also the growth of A498, HOP‐62, and HOP‐92 with GI 50 values of 17.0, 20.0, and 21.8 μ M , respectively.