title: Relayed Regioselective Alkynylation/Olefination of Unsymmetrical Cyclic Diaryliodonium Species Catalyzed by Cu and Pd: Affording Fluorescent Cytotoxic Benzoxazoles.
abstract: Although cyclic diaryliodonium species have the potential to act as valuable synthons for cascade transformations, they still remain largely unexplored. The regioselectivity associated with unsymmetrical cyclic diaryliodonium species has previously been known to pose a challenge. A regioselective relayed alkynylation and olefination of unsymmetrical cyclic diaryliodonium species has been achieved by installation of a directing amido group. These relayed transformations were delayed until an oxazole ring had formed, delivering a series of unique fluorescent benzoxazoles. Moreover, some of these synthetic benzoxazoles showed apparent inhibitory activity against malignant cancer cells. Further confocal visualization revealed that benzoxazoles targeted cell nuclei. These findings might provide a novel structural scaffold to develop desirable anticancer agents.
authors.affiliation: Sun Yat-sen University Cancer Center, State Key Laboratory of Oncology in South China, Collaborative Innovation Center for Cancer Medicine, Sun Yat-sen University 651 Dongfeng East Road, Guangzhou 510060 (China).|School of Pharmaceutical Sciences, Sun Yat-sen University, 132 Waihuan East Road, Guangzhou 510006 (China).
authors.forename: Daqian
authors.initials: D
authors.lastname: Zhu
authors.affiliation: Sun Yat-sen University Cancer Center, State Key Laboratory of Oncology in South China, Collaborative Innovation Center for Cancer Medicine, Sun Yat-sen University 651 Dongfeng East Road, Guangzhou 510060 (China).
authors.forename: Panpan
authors.initials: P
authors.lastname: Liu
authors.affiliation: Sun Yat-sen University Cancer Center, State Key Laboratory of Oncology in South China, Collaborative Innovation Center for Cancer Medicine, Sun Yat-sen University 651 Dongfeng East Road, Guangzhou 510060 (China).
authors.forename: Wenhua
authors.initials: W
authors.lastname: Lu
authors.affiliation: School of Pharmaceutical Sciences, Sun Yat-sen University, 132 Waihuan East Road, Guangzhou 510006 (China).
authors.forename: Haiwen
authors.initials: H
authors.lastname: Wang
authors.affiliation: Sun Yat-sen University Cancer Center, State Key Laboratory of Oncology in South China, Collaborative Innovation Center for Cancer Medicine, Sun Yat-sen University 651 Dongfeng East Road, Guangzhou 510060 (China).|School of Pharmaceutical Sciences, Sun Yat-sen University, 132 Waihuan East Road, Guangzhou 510006 (China).
authors.forename: Bingling
authors.initials: B
authors.lastname: Luo
authors.affiliation: Sun Yat-sen University Cancer Center, State Key Laboratory of Oncology in South China, Collaborative Innovation Center for Cancer Medicine, Sun Yat-sen University 651 Dongfeng East Road, Guangzhou 510060 (China).
authors.forename: Yumin
authors.initials: Y
authors.lastname: Hu
authors.affiliation: Sun Yat-sen University Cancer Center, State Key Laboratory of Oncology in South China, Collaborative Innovation Center for Cancer Medicine, Sun Yat-sen University 651 Dongfeng East Road, Guangzhou 510060 (China). huangpeng@sysucc.org.cn.
authors.forename: Peng
authors.initials: P
authors.lastname: Huang
authors.affiliation: Sun Yat-sen University Cancer Center, State Key Laboratory of Oncology in South China, Collaborative Innovation Center for Cancer Medicine, Sun Yat-sen University 651 Dongfeng East Road, Guangzhou 510060 (China). wenshj@sysucc.org.cn.|School of Pharmaceutical Sciences, Sun Yat-sen University, 132 Waihuan East Road, Guangzhou 510006 (China). wenshj@sysucc.org.cn.
authors.forename: Shijun
authors.initials: S
authors.lastname: Wen
mesh_terms: D001583:Benzoxazoles / Q000737:chemistry* / Q000633:toxicity*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry* / Q000633:toxicity*; D015394:Molecular Structure; D009861:Onium Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001583:Benzoxazoles; D005456:Fluorescent Dyes; D009861:Onium Compounds; D010165:Palladium; D003300:Copper
keywords: alkynylation; fluorescence; iodonium; olefination; regioselectivity