Total synthesis and RXR伪-mediated transcription studies of neriifolone B and related compounds

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• 作者：Qirong Shen^a ; ^&dagger ; ; Yi Dai^b ; ^&dagger ; ; Guanghui Wang^c ; Fei Yao^a ; Yinghui Duan^b ; Haifeng Chen^c ; Weige Zhang^a ; ^{zhangweige2000@sina.com" class="auth_mail} ; Xiaokun Zhang^c ; Xinsheng Yao^b ; ^{tyaoxs@jnu.edu.cn" class="auth_mail}
• 关键词：Total synthesis ; Xanthone ; RXR伪 transcriptional inhibitory activity
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：1 May, 2014
• 年：2014
• 卷：22
• 期：9
• 页码：2671-2677
• 全文大小：773 K

文摘

Neriifolone B (1), a natural product containing a novel 4鈥?4鈥?dimethyl-4鈥?5鈥?dihydropyran-6-one[2鈥?3鈥?3,4]xanthone skeleton, was found to be a potent inhibitor of transcription mediated by retinoid X receptor 伪 (RXR伪). The first total synthesis of neriifolone B (1) was achieved in 14 steps with an overall yield of 7.1%. A Claisen rearrangement was employed as the key step in the sequence. The activity of six natural xanthones and eight compounds related to neriifolone B (1) against RXR伪-mediated transcription was evaluated. Two neriifolone B analogs, 17 and 11鈥? were potent inhibitors of RXR伪 transcriptional activity. Preliminary structure-activity relationship studies are discussed briefly.