Synthesis, characterization, and in vitro SAR evaluation of N,N′-bis(arylmethyl)-C²-alkyl substituted imidazolium salts

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• 作者：Michael A. DeBord ; Patrick O. Wagers ; Steven R. Crabtree ; Claire A. Tessier ; Matthew J. Panzner ; ^{mjp9@uakron.edu} ; Wiley J. Youngs ; ^{youngs@uakron.edu}
• 关键词：Imidazolium salt ; Anti-cancer ; Anti-tumor ; Non-small cell lung cancer ; Quinoline ; Naphthalene
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2017
• 出版时间：15 January 2017
• 年：2017
• 卷：27
• 期：2
• 页码：196-202
• 全文大小：1010 K
• 卷排序：27

文摘

A series of C2-alkyl substituted N,N′-bis(arylmethyl)imidazolium salts were synthesized, characterized, and tested for their in vitro anti-cancer activity against multiple non-small cell lung cancer cell lines by our group and the National Cancer Institute’s-60 human tumor cell line screen to establish a structure-activity relationship. Compounds are related to previously published N,N′-bis(arylmethyl)imidazolium salts but utilize the historical quinoline motif and anion effects to increase the aqueous solubility. Multiple derivatives displayed high anti-cancer activity with IC50 values in the nanomolar to low micromolar range against a panel of non-small cell lung cancer cell lines. Several of these derivatives have high aqueous solubilities with potent anti-proliferative properties and are ideal candidates for future in vivo xenograft studies and have high potential to progress into clinic use.