Copper-Catalyzed Dearomative [3 + 2] Annulation of Indoles with 2-Iodoacetic Acid DOI
Ren‐Xiao Liang,

Hu-Jie Cai,

Ming‐Hua Mao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(45), P. 9631 - 9636

Published: Nov. 4, 2024

An efficient copper-catalyzed dearomative [3 + 2] annulation of indoles with 2-iodoacetic acid is developed. By employing Cu(OTf)2/2,2′-bis(2-oxazoline) as the catalyst and LPO oxidant, a series indoline-fused butyrolactones were synthesized in moderate to good yields. The reaction features mild conditions, broad substrate scope, readily available starting materials. Furthermore, synthetic transformations products conducted demonstrate practical utility this reaction.

Language: Английский

Discovery of Novel Oxazolo[4,3-f]purine Derivatives as Antitumor Agents through PPIA Interaction DOI
Xian-Jia Li,

Meng‐Cheng Zhang,

Xiang Li

et al.

Journal of Medicinal Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 26, 2025

54 novel oxazolo [4,3-f]purine derivatives were designed, synthesized, and evaluated for antitumor activity, among which compound 20b exhibited potent activity against several cancer cell lines. Compound inhibited metastasis, arrested the cycle in G0/G1 phase, induced apoptosis HCT116 cells. Mechanistic studies revealed that increased ROS levels led to DNA damage, endoplasmic reticulum (ER) stress, mitochondrial dysfunction Limited proteolysis-small molecule mapping (LiP-SMap), drug affinity responsive target stability (DARTS) assay, cellular thermal shift assay (CETSA), surface plasmon resonance (SPR) experiments provided evidence bound PPIA with a KD value of 0.52 μM. siRNA indicated 20b-mediated antiproliferative antimigration activities abolished PPIA/MAPK signaling pathway was when silenced Significantly, presented significant anticolorectal efficacy vivo without obvious toxicity. These results indicate may serve as anticancer agent targeting PPIA, meriting further attention research.

Language: Английский

Citations

0
Strain-Release Glycosylation of Thio- and Selenoglycosides Enabled by Activation of Donor–Acceptor Oxiranes with Catalytic TfOH DOI

Xin-Yu Fang,

Liu Xingle,

Jiaying Shen

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

We have developed a strain-release glycosylation method for thio/selenoglycosides utilizing donor-acceptor oxiranes (DAOs) and triflic acid (2 mol %) via C-C bond cleavage under ambient conditions. This protocol is effective acid-sensitive sterically hindered substrates, demonstrating broad applicability. Experimental results DFT calculations reveal that DAO/TfOH-derived zwitterionic oxocarbenium species activate donors glycosyl zwitterion intermediates, facilitating glycosidic formation proton transfer. approach pioneers epoxide-mediated activation, offering mild, efficient platform diverse glycoside synthesis advancing methodologies in carbohydrate chemistry.

Language: Английский

Citations

0
Recent developments in enantioselective nickel-catalysed cycloadditions DOI

Hélène Pellissier

Tetrahedron, Journal Year: 2024, Volume and Issue: 153, P. 133840 - 133840

Published: Jan. 20, 2024

Language: Английский

Citations

2
Dearomative [4 + 2] Annulation of Electron-Poor N-Heteroarenes with Azoalkenes for Access to Polycyclic Tetrahydro-1,2,4-triazines DOI
Dong‐Chao Wang, Jiahui Liu, Yuqing Guan

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(19), P. 3543 - 3547

Published: May 9, 2023

A direct dearomative [4 + 2] annulation of electron-poor N-heteroarenes with azoalkenes generated in situ from α-halogeno hydrazones was developed under mild conditions. Accordingly, a series fused polycyclic tetrahydro-1,2,4-triazines potential biological activity were obtained up to 96% yield. Various and N-heteroarenes, such as pyridines, quinolines, isoquinolines, phenanthridine, benzothiazole, tolerated by this reaction. The general applicability method shown upscale synthesis product derivatization.

Language: Английский

Citations

6
Is it still worth renewing nucleoside anticancer drugs nowadays? DOI
Zai‐Qun Liu

European Journal of Medicinal Chemistry, Journal Year: 2023, Volume and Issue: 264, P. 115987 - 115987

Published: Nov. 24, 2023

Language: Английский

Citations

5
Synthesis of 2‐Substituted‐4,5‐Dihydrothiazol‐4‐Ols by [3 + 2] Annulation of 1,4‐Dithiane‐2,5‐Diol with Thioamides DOI
Xiantao Ma,

Meng‐Cheng Zhang,

Yuying Chen

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

Abstract We developed a novel method for the synthesis of 2‐substituted‐4,5‐dihydrothiazol‐4‐ols compounds through cyclization thioamides and 1,4‐dithiane‐2,5‐diol in presence Et 3 N. Stable hydroxy‐substituted thiazole were isolated substituted thioamides. The reaction conditions are simple, substrate range is wide, target obtained up to 82 % yield.

Language: Английский

Citations

1
Dearomative [2 + 1] Spiroannulation of Bromophenols with Electron-Deficient Alkenes DOI
Tingting Yang,

Yun-Qiao Zhang,

Ming‐Sheng Xie

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 8041 - 8054

Published: May 17, 2024

A base-assisted dearomative [2 + 1] spiroannulation of p/o-bromophenols with activated olefins (methylenemalonates) to construct various cyclopropyl spirocyclohexadienone skeletons is reported. Furthermore, several other halophenols (X = Cl, I) were also tolerated in this process. Control experiments reveal a Michael addition phenols at their halogenated positions methylenemalonates, followed by intramolecular radical-based SRN1 dehalogenative cyclopropanation. However, according the density functional theory (DFT) calculations, an SN2 cyclopropanation same low activation energy barrier should not be excluded. The utility method showcased gram-scale syntheses and transformations dearomatized products.

Language: Английский

Citations

0
Organocatalytic Dearomatization of 5-Aminopyrazoles: Synthesis of 4-Hydroxypyrazolines DOI
Pradeep Natarajan,

Subhashini V. Subramaniam,

S. Peruncheralathan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10258 - 10271

Published: July 11, 2024

Dearomatization is a fundamental chemical reaction that affords complex three-dimensional heterocyclic frameworks. We disclose the first organocatalytic dearomatization of 5-aminopyrazoles, which yields range structurally diversified C4-hydroxylated pyrazolines with ≤95% in <1.5 h at room temperature. This catalytic process achieved using

Language: Английский

Citations

0
Copper-Catalyzed Dearomative [3 + 2] Annulation of Indoles with 2-Iodoacetic Acid DOI
Ren‐Xiao Liang,

Hu-Jie Cai,

Ming‐Hua Mao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(45), P. 9631 - 9636

Published: Nov. 4, 2024

An efficient copper-catalyzed dearomative [3 + 2] annulation of indoles with 2-iodoacetic acid is developed. By employing Cu(OTf)2/2,2′-bis(2-oxazoline) as the catalyst and LPO oxidant, a series indoline-fused butyrolactones were synthesized in moderate to good yields. The reaction features mild conditions, broad substrate scope, readily available starting materials. Furthermore, synthetic transformations products conducted demonstrate practical utility this reaction.

Language: Английский

Citations

0