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
Synthesis of Natural Product-like Indeno[2,1-b]indole/Shikimic Acid Hybrid Analogues with Anti-osteoclastogenic Activity via Photo-Nazarov Reaction

文献类型：期刊论文

作者Shao, Zhengguang2,3,4; Wang, Tianqi1; Zhang, Xiaofei4; Jiang, Min1; Zhu, Weiliang4; Ning, Ruonan1; Yang, Chunhao2,3,4
刊名EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
出版日期2024-11-06
页码8
关键词Natural product-like molecule Indeno[2,1-b]indole Shikimic acid Photo-Nazarov Diatereoselectivity
ISSN号1434-193X
DOI10.1002/ejoc.202400933
英文摘要Indeno[2,1-b]indole and shikimic acid-like structures are natural privileged scaffolds in several bioactive NPs. In this work, we developed a high-efficient and diastereoselective synthetic approach to construct novel indeno[2,1-b]indole/shikimic acid hybrid analogues via photo-Nazarov reaction. The protocol is the first case of excited-state photo-Nazarov cyclization of indole-2-yl vinyl ketone to indeno[2,1-b]indole. (6aS, 10aR)-products were afforded in moderate to good yields (37-92 %) for most of substrates (91 % for model substrate 1 aa) after the condition optimization. Even more attractive, several synthesized analogues (2 t, 3 c and 3 d) exhibited potent RANKL-induced osteoclastogenesis inhibitory activities (inhibitory rate >50 % at 5 mu M), which suggested promising prospect of the novel tetracyclic indeno[2,1-b]indole/shikimic acid hybrid scaffold for anti-osteoporosis drug development.
WOS关键词TRIACETYLSHIKIMIC ACID ; BIOLOGICAL EVALUATION ; CYCLIZATION
资助项目State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica ; [SKLDR-2023-KF-06]
WOS研究方向Chemistry
WOS记录号WOS:001355503800001
出版者WILEY-V C H VERLAG GMBH
源URL[http://119.78.100.183/handle/2S10ELR8/314415]  
专题新药研究国家重点实验室
通讯作者Ning, Ruonan; Yang, Chunhao
作者单位1.Shanghai Jiao Tong Univ, Sch Med, Shanghai Key Lab Prevent & Treatment Bone & Joint, Shanghai Inst Traumatol & Orthopaed,Ruijin Hosp,De, Shanghai 200025, Peoples R China
2.ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China
3.Lingang Lab, Shanghai 200021, Peoples R China
4.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China
推荐引用方式
GB/T 7714		 Shao, Zhengguang,Wang, Tianqi,Zhang, Xiaofei,et al. Synthesis of Natural Product-like Indeno[2,1-b]indole/Shikimic Acid Hybrid Analogues with Anti-osteoclastogenic Activity via Photo-Nazarov Reaction[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2024:8.
APA Shao, Zhengguang.,Wang, Tianqi.,Zhang, Xiaofei.,Jiang, Min.,Zhu, Weiliang.,...&Yang, Chunhao.(2024).Synthesis of Natural Product-like Indeno[2,1-b]indole/Shikimic Acid Hybrid Analogues with Anti-osteoclastogenic Activity via Photo-Nazarov Reaction.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,8.
MLA Shao, Zhengguang,et al."Synthesis of Natural Product-like Indeno[2,1-b]indole/Shikimic Acid Hybrid Analogues with Anti-osteoclastogenic Activity via Photo-Nazarov Reaction".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2024):8.

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。