中国科学院机构知识库网格
Chinese Academy of Sciences Institutional Repositories Grid
首页 机构 成果 学者
  
  1. CAS IR Grid
  2. 上海药物研究所
  3. 中国科学院上海药物研究所
  4. 新药研究国家重点实验室
Concise syntheses of (+)-maximumins B and C and (+)-ottensinin

文献类型：期刊论文

作者Li, Qing-Xin3,4; Wang, Lin-Lin1,2; Zheng, Yue-Ming2,3; Gao, Zhao-Bing1,2,3; Zhao, Jin-Xin3,4; Yue, Jian-Min1,3,4
刊名ORGANIC CHEMISTRY FRONTIERS
出版日期2024-07-26
页码7
ISSN号2052-4129
DOI10.1039/d4qo00878b
通讯作者Gao, Zhao-Bing(zbgao@simm.ac.cn) ; Zhao, Jin-Xin(jxzhao@simm.ac.cn) ; Yue, Jian-Min(jmyue@simm.ac.cn)
英文摘要Maximumin B (1), maximumin C (2), and ottensinin (3) are three rearranged labdane diterpenoids featuring a unique 3-substituted gamma-pyrone motif. Herein, we report the first syntheses of (+)-1 and (+)-2 and an improved synthesis of (+)-3 in 4-12 steps. Key features for the syntheses of 1 and 2 include a Pd-catalyzed decarboxylative coupling reaction establishing the 3-substituted gamma-pyrone and a Baran decarboxylative coupling enabling ketone formation in the final step. A Ni-catalyzed C(sp2)-C(sp3) cross-electrophile coupling reaction was applied to accomplish the synthesis of 3. Furthermore, in-depth pharmacological screening unveiled ottensinin (3) as a potent KCNQ2 agonist exhibiting comparable potency to retigabine, making it a promising lead for the development of a novel class of anti-epileptic drugs. Three rearranged labdane diterpenoids, featuring a common 3-substituted gamma-pyrone, were effectively synthesized with the longest linear sequences of 4-12 steps. The in-depth pharmacological screening unveiled (+)-ottensinin as a potent KCNQ2 agonist.
WOS关键词ENANTIOSELECTIVE TOTAL-SYNTHESIS ; LABDANE-TYPE DITERPENOIDS ; NF-KAPPA-B ; NORDITERPENOIDS ; TERPENOIDS ; RHIZOMES ; HALIDES ; KV1.3
资助项目National Key Research and Development Program of China[2023YFE0206100] ; National Natural Science Foundation of China[22237007] ; National Natural Science Foundation of China[T2192972] ; Youth Innovation Promotion Association of Chinese Academy of Sciences[2022282]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001281717400001
出版者ROYAL SOC CHEMISTRY
源URL[http://119.78.100.183/handle/2S10ELR8/312580]  
专题新药研究国家重点实验室
通讯作者Gao, Zhao-Bing; Zhao, Jin-Xin; Yue, Jian-Min
作者单位1.Nanjing Univ Chinese Med, Sch Chinese Mat Med, 138 Xianlin Rd, Nanjing 210023, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, Ctr Neurol & Psychiat Res & Drug Discovery, 501 Haike Rd, Shanghai 201203, Peoples R China
3.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China
4.Chinese Acad Sci, Shanghai Inst Mat Med, Ethnomed & Biofunct Mol Res Ctr, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China
推荐引用方式
GB/T 7714		 Li, Qing-Xin,Wang, Lin-Lin,Zheng, Yue-Ming,et al. Concise syntheses of (+)-maximumins B and C and (+)-ottensinin[J]. ORGANIC CHEMISTRY FRONTIERS,2024:7.
APA Li, Qing-Xin,Wang, Lin-Lin,Zheng, Yue-Ming,Gao, Zhao-Bing,Zhao, Jin-Xin,&Yue, Jian-Min.(2024).Concise syntheses of (+)-maximumins B and C and (+)-ottensinin.ORGANIC CHEMISTRY FRONTIERS,7.
MLA Li, Qing-Xin,et al."Concise syntheses of (+)-maximumins B and C and (+)-ottensinin".ORGANIC CHEMISTRY FRONTIERS (2024):7.

入库方式： OAI收割

来源：上海药物研究所

浏览0
下载0
收藏0
其他版本

除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。