5635-16-5Relevant articles and documents
A Unified Approach for Divergent Synthesis of Heterocycles via TMSOTf-Catalyzed Formal [3+2] Cycloaddition of Electron-Rich Alkynes
Chen, Ping,Cao, Wei,Li, Xiangqian,Shi, Dayong
supporting information, p. 4789 - 4794 (2021/09/02)
We present a synthetic protocol for the construction of polysubstituted five-membered heterocycles via TMSOTf-catalyzed formal [3+2] cycloaddition of electron-rich alkynes, which features free from any metal, atom economy and water as the main by-product. Furthermore, alkenyl ether adduct has been verified as the key intermediate. Notably, by utilizing this approach, we can synthesize a broad range of polysubstituted furans, thiophenes and pyrroles, and extend this transformation to deliver fused-polyheterocycles. This reaction can be achieved on a gram scale and the corresponding products are intermediates for producing diverse potentially useful scaffolds. (Figure presented.).
Two-step synthesis of π-expanded maleimides from 3,4-diphenylfuran-2(5 H)-ones
Kang, Yang,Zhang, Wei,Wang, Tao,Liang, Yong,Zhang, Zunting
, p. 12387 - 12398 (2019/10/11)
An efficient two-step synthesis of -expanded maleimide derivatives was reported, which proceeded via a photoinduced dehydrogenative annulation of 3,4-diphenylfuran-2(5H)-ones in EtOH at room temperature for 5 h under an argon atmosphere, followed by inter
Design of fluorine-containing 3,4-diarylfuran-2(5H)-ones as selective COX-1 inhibitors
Uddin, Md. Jashim,Elleman, Anna V.,Ghebreselasie, Kebreab,Daniel, Cristina K.,Crews, Brenda C.,Nance, Kellie D.,Huda, Tamanna,Marnett, Lawrence J.
supporting information, p. 1254 - 1258 (2015/04/27)
We report the design and synthesis of fluorine-containing cyclooxygenase-1 (COX-1)-selective inhibitors to serve as prototypes for the development of a COX-1-targeted imaging agent. Deletion of the SO2CH3 group of rofecoxib switches the compound from a COX-2- to a COX-1-selective inhibitor, providing a 3,4-diarylfuran-2(5H)-one scaffold for structure-activity relationship studies of COX-1 inhibition. A wide range of fluorine-containing 3,4-diarylfuran-2(5H)-ones were designed, synthesized, and tested for their ability to selectively inhibit COX-1 in purified protein and human cancer cell assays. Compounds containing a fluoro-substituent on the C-3 phenyl ring and a methoxy-substituent on the C-4 phenyl ring of the 3,4-diarylfuran-2(5H)-one scaffold were the best COX-1-selective agents of those evaluated, exhibiting IC50s in the submicromolar range. These compounds provide the foundation for development of an agent to facilitate radiologic imaging of ovarian cancer expressing elevated levels of COX-1.
