81402-06-4Relevant articles and documents
Synthesis and Properties of 6-(Hydroxymethyl)-9,9,10,10-tetracyanonaphthoquinodimethane
Torres, Epifanio,Panetta, Charles A.,Heimer, Norman E.,Clark, Bobbie J.,Hussey, Charles L.
, p. 3737 - 3739 (1991)
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6-Substituted 1,4-naphthoquinone oxime derivatives (I): synthesis and evaluation of their cytotoxic activity
Huang, Guang,Zhao, Hui-ran,Zhou, Wen,Dong, Jin-yun,Zhang, Qi-jing,Meng, Qing-qing,Zhu, Bao-quan,Li, Shao-shun
, p. 1011 - 1023 (2017/05/12)
Abstract: A series of 6-substituted 1,4-naphthoquinone oxime derivatives were synthesized and evaluated for their in vitro cytotoxicity against four cancer cell lines and one normal cell line. Some compounds exhibited moderate to good cytotoxicity towards cancer cells and meanwhile all the synthesized compounds displayed no apparent cytotoxic activity against normal cells (IC50?>?100?μM). Among these oxime derivatives, three compounds showed more potent cytotoxicity against human colon cancer cell lines (HCT-15) than adriamycin and 5-fluorouracil, with an IC50 value of 2.52, 1.96, and 2.27?μM, respectively. Additionally, structure–activity relationship studies revealed that cytotoxic effects of these oxime derivatives were not only largely dependent upon the size of alkyl chain R1, but also upon substituents R2 of the branch chain, indicating that the strong cytotoxicity of these compounds was ascribed to their appropriate lipophilicity. Collectively, this study could provide available strategy for design and synthesis of 6-substituted 1,4-naphthoquinone oxime derivatives as potential anticancer agents. Graphical abstract: [Figure not available: see fulltext.].
2-and 6-methyl-1,4-naphthoquinone derivatives as potential bioreductive alkylating agents
Antonini,Lin,Cosby,Dai,Sartorelli
, p. 730 - 735 (2007/10/02)
A number of antineoplastic agents possess both the quinone nucleus and an appropriate substituent that permits them to function as bioreductive alkylating agents. To develop new compounds of this type with unique properties, the authors have synthesized a