Catalytic [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes: non-carbenoid Doyle–Kirmse reaction DOI

Fu‐Yuan Yang,

Tian‐Jiao Han,

Shi‐Kun Jia

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(21), P. 3107 - 3110

Published: Jan. 1, 2023

The Sc(III)-catalyzed [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes has been established. Owing to the absence a carbenoid intermediate, this protocol represents first non-carbenoid variant Doyle-Kirmse reaction. Under mild conditions, variety tertiary thioethers have readily prepared in good excellent yields.

Language: Английский

Unveiling a pyrroloindoline diketopiperazine biosynthetic pathway featuring a phytoene-synthases-like family prenyltransferase with distinct regioselectivity DOI

He Duan,

Meifang Zhang,

Zhenshan Chen

et al.

Bioorganic Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 108448 - 108448

Published: April 1, 2025

Language: Английский

Citations

0
Discovery and cytotoxic activity of N-CF3-containing pyrroloindolines DOI

Qigang Sun,

Jun‐Yunzi Wu,

Yu Zhang

et al.

Research Square (Research Square), Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

Abstract Pyrroloindoline scaffolds are widely found in numerous biologically active and medicinally significant natural products. Meanwhile, the potential applications of N-CF3 compounds medicinal chemistry have garnered increasing attention due to their unique properties. However, pharmacological activities therapeutic N-CF3-containing pyrroloindolines remain underexplored. Building on our previously developed method for constructing pyrroloindoline scaffolds, this study systematically evaluated antitumor a diverse series N-CF₃-containing derivatives. Cell-based assays demonstrated that these derivatives exhibited antiproliferative against human cancer cell lines, including 786-O, A498, HepG2. Further investigations revealed not only induce apoptosis cells but also inhibit colony formation. Moreover, they showed suppress metastasis proliferation, primarily by inducing cycle arrest. These findings suggest hold great promise as anticancer agents merit further development.

Language: Английский

Citations

0
Visible-light-driven reductive dearomatization of N-arylformyl indoles in EDA complexes with a thiophenol via a HAT pathway DOI
Cai Yiping,

Meng‐Yue Ma,

Xiao Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(7), P. 1633 - 1642

Published: Jan. 1, 2023

A visible light-driven dearomatization of an N -( o -haloarylformyl)indole in electron donor–acceptor (EDA) complex with a thiophenol. The radical reaction is terminated by concerted hydrogen atom transfer (HAT).

Language: Английский

Citations

10
Catalytic asymmetric de novo construction of 4-pyrrolin-2-ones via intermolecular formal [3+2] cycloaddition of azoalkenes with azlactones DOI

Nan-Nan Mo,

Yu‐Hang Miao, Xiao Xiao

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(39), P. 5902 - 5905

Published: Jan. 1, 2023

The chiral phosphoric acid-catalyzed asymmetric intermolecular formal [3+2] cycloaddition of azoalkenes with azlactones has been established. This convergent protocol leads to a facile and enantioselective de novo construction wide range fully substituted 4-pyrrolin-2-ones bearing carbon atom in good yields excellent enantioselectivities (26 examples, 72-95% 87-99% ee).

Language: Английский

Citations

10
Catalytic [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes: non-carbenoid Doyle–Kirmse reaction DOI

Fu‐Yuan Yang,

Tian‐Jiao Han,

Shi‐Kun Jia

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(21), P. 3107 - 3110

Published: Jan. 1, 2023

The Sc(III)-catalyzed [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes has been established. Owing to the absence a carbenoid intermediate, this protocol represents first non-carbenoid variant Doyle-Kirmse reaction. Under mild conditions, variety tertiary thioethers have readily prepared in good excellent yields.

Language: Английский

Citations

9