Cited by A solvent controlled regioselective synthesis of 2- and 4-substituted α-carbolines under palladium catalysis

Naturally derived indole alkaloids targeting regulated cell death (RCD) for cancer therapy: from molecular mechanisms to potential therapeutic targets DOI

Rui Qin,

Feng‐Ming You,

Qian Zhao

et al.

Journal of Hematology & Oncology, Journal Year: 2022, Volume and Issue: 15(1)

Published: Sept. 14, 2022

Abstract Regulated cell death (RCD) is a critical and active process that controlled by specific signal transduction pathways can be regulated genetic signals or drug interventions. Meanwhile, RCD closely related to the occurrence therapy of multiple human cancers. Generally, subroutines are key tumorigenesis, which contributed our better understanding cancer pathogenesis therapeutics. Indole alkaloids derived from natural sources well defined for their outstanding biological pharmacological properties, like vincristine, vinblastine, staurosporine, indirubin, 3,3′-diindolylmethane, currently used in clinic under clinical assessment. Moreover, such compounds play significant role discovering novel anticancer agents. Thus, here we systemically summarized recent advances indole as agents targeting different subroutines, including classical apoptosis autophagic signaling crucial other ferroptosis, mitotic catastrophe, necroptosis, anoikis, cancer. further discussed cross talk between mediated combined strategies (e.g., 3,10-dibromofascaplysin with olaparib) exhibit therapeutic potential against various cancers regulating subroutines. In short, information provided this review on regulation targets expected beneficial design molecules greater thereby facilitating development new therapy. Graphic abstract

Language: Английский

Citations

Lewis-Base-Catalyzed Enantioselective Formal [4 + 2] Annulations of Morita–Baylis–Hillman Carbonates: Access to Tetrahydroquinolines Derivatives DOI

Yanlin He,

Wei Cai, You Huang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(19), P. 3347 - 3351

Published: May 10, 2023

The Lewis-base-catalyzed enantioselective formal [4 + 2] annulation reaction of o-acylamino-aryl MBH carbonates and electron-deficient olefins was developed. Tetrahydroquinolines with three sequential stereogenic centers containing a quaternary stereocenter were obtained in high yields good enantioselectivity.

Language: Английский

Citations

Convenient Synthetic Protocols for Diverse Functionalized Dihydrobenzofuran-Fused Spiro-indanedione-oxindole Scaffolds DOI

Jing Sun,

Xueyan Liu, Qiu Sun

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(16), P. 11562 - 11580

Published: July 27, 2023

Diverse functionalized dihydrobenzofuran spiro-indanedione-oxindole scaffolds were conveniently synthesized by base-promoted cyclization reaction of Morita-Baylis-Hillman (MBH) carbonates isatins and 2-(o-hydroxybenzylidene)-1,3-indanediones. The two diastereomeric dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines] could be selectively using DABCO or DMAP as a base promoter. More importantly, facilitated the annulation MBH formates 2-(o-hydroxybenzylidene)-1,3-indanediones selectively, resulting in spiro[cyclopropa[c]chromene-1,2'-indene]-1',3'-diones dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines]. Additionally, similar with maleimides afforded dispiro[indene-2,5'-benzofuro[2',3':1,5]cyclopenta[1,2-c]pyrrole-4',3″'-indolines] high yields diastereoselectivity.

Language: Английский

Citations

Synthesis of Spiro[indoline-pyridine]-dicarboxylates and Substituted Alkylidene Oxindoles by Azomethine Ylides and MBH Carbonates of Isatins DOI

Daqian Wang, Ting Tang,

Jing Sun

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(19), P. 4117 - 4121

Published: May 9, 2024

We have developed an efficient protocol for the synthesis of spiro[indoline-pyridine]dicarboxylates and substituted alkylidene oxindoles through [3 + 3] cycloaddition Michael addition individually by azomethine ylides various MBH carbonates isatins. The selective generation cyclic products chain was achieved changing substituents at 3-position oxindoles. features this method include convenient catalysts, mild reaction conditions, broad substrate scopes.

Language: Английский

Citations

An Access to Highly Functionalized Dihydrobenzofuran Spirooxindole Scaffolds DOI

Daqian Wang,

Jing Sun,

Ying Han

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(42), P. 7790 - 7795

Published: Oct. 14, 2022

We have developed an efficient protocol for the construction of polycyclic dihydrobenzofuran spirooxindole scaffolds via base promoted cascade annulation Morita-Baylis-Hillman (MBH) carbonates isatins with ortho-hydroxychalcones or ortho-hydroxy-β-nitrostyrenes. The complex compounds were conveniently synthesized in satisfactory yields and high diastereoselectivity. This provides a swift convenient approach assembly diverse highly functionalized spirooxindoles also features broad substrate scope, molecular convergence, excellent atomic economy.

Language: Английский

Citations

Selective construction of spiro[indoline-3,5′-pyrrolo[3,4-b]azepines] and spiro[indoline-3,3′-pyrroles] via a [4 + 3]/[3 + 2] cycloaddition reaction of α,β-unsaturated aldimines and MBH adducts of isatins DOI

Dan Liu,

Jing Sun,

Qiu Sun

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 10(2), P. 540 - 547

Published: Dec. 10, 2022

An efficient synthetic protocol for the selective construction of spiro[indoline-3,5′-pyrrolo[3,4- b ]azepines] and spiro[indoline-3,3′-pyrroles] via a cycloaddition reaction α,β-unsaturated aldimines MBH adducts isatins was successfully developed.

Language: Английский

Citations

Cooperative photoactivation/Lewis base catalyzed [4 + 2] annulations of α-diazoketones andortho-amino MBH carbonates to access dihydroquinolinone frameworks DOI

Jin Zhou, Chen Chen, Qiwen Pang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(4), P. 1034 - 1041

Published: Jan. 1, 2023

A series of dihydroquinolinones have been synthesized via synergistic catalysis combining photolysis and Lewis base utilizing in situ generated ketenes ortho -amino MBH carbonates.

Language: Английский

Citations

Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles DOI

Qing‐Feng Li, Jing Ma,

Junjia Meng

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4412 - 4439

Published: Nov. 16, 2023

Abstract Spirooxindoles are privileged scaffolds in diverse bioactive natural products and pharmaceuticals, significant achievements for the construction of these molecules have thus been made past years. Among them, organocatalysis, particular, nucleophilic Lewis base catalysis, has recently emerged as an efficient reliable method preparation valuable functionalized spirooxindoles. According to different kinds catalysts, we summarize classify three catalytic strategies; tertiary amine‐catalyzed cycloadditions, NHC‐catalyzed phosphine‐catalyzed respectively. Through methods, potential spirooxindole skeletons owning various functional groups can be produced enrich small organic molecule library. In this review, describe a comprehensive updated advances cycloaddition reactions Meanwhile, related mechanism application annulation strategies product total synthesis will highlighted detail.

Language: Английский

Citations

Efficient construction of diverse spiro[indoline-3,4′-pyrrolo[3,4-b]pyridines] via [3 + 3] cycloaddition of MBH carbonates of isatins with β-enamino maleimides DOI

Liu‐Na Pan,

Jing Sun,

Xueyan Liu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(35), P. 7099 - 7104

Published: Jan. 1, 2022

An efficient method to construct unique spiro[indoline-3,4′-pyrrolo[3,4- b ]pyridines] was successfully developed via a DABCO promoted formal [3 + 3] cycloaddition reaction of MBH carbonates isatins with β-enamino maleimides under mild conditions.

Language: Английский

Citations

Enantioselective Construction of Tetrahydro‐α‐Carbolines via Organocatalytic Friedel‐Crafts alkylation/N‐hemiacetalization of 2‐aminoindoles with Enals DOI

Xiaochun Liu,

Xiang‐Feng Ding,

Yangzi Liu

et al.

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 21, 2025

Abstract An efficient organocatalytic asymmetric Friedel‐Crafts alkylation/ N ‐hemiacetalization reaction of 2‐aminoindoles with α,β‐unsaturated aldehydes was developed. By incorporating an amino group at the C2 position indole, nucleophilicity C3 indole and were leveraged to generate enamine‐type ternary synthon. This approach enabled construction a range chiral tetrahydro‐α‐carboline skeletons potential biological activity, delivering moderate excellent yields (46–83 %) achieving outstanding enantioselectivity (up 99 % ee).

Language: Английский

Citations