Efficient Synthesis of N-(9-Xanthyl)-4-Toluenesulfonamides Enabled by an Addition-Cyclization Cascade of Arynes

Lu, Shouci; Lu, Chong‐Dao

doi:10.1055/s-0032-1318311

Cited by 8 publications

(6 citation statements)

References 2 publications

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“…The resulted product N-(2-hydroxybenzylidene)-4-methylbenzenesulfonamide was reacted with 2-(trimethylsilyl)phenyl trifluoromethanesulfonate in the presence of potassium fluoride, 18-crown ether and tetrahydrofuran to afford the final product in an overall yield of 58%. The 1 H-NMR spectrum was consistent with the published data (21–22). …”

Section: Methodssupporting

confidence: 89%

Free-fatty acid receptor-4 (FFA4) modulates ROS generation and COX-2 expression via the C-terminal β-arrestin phosphosensor in Raw 264.7 macrophages

Cheshmehkani

Senatorov

Dhuguru

et al. 2017

Biochemical Pharmacology

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Agonism of the G protein-coupled Free-Fatty Acid receptor-4 (FFA4) has been shown to promote numerous anti-inflammatory effects in macrophages that arise due to interaction with β-arrestin partner proteins. Humans express functionally distinct short and long FFA4 splice variants, such that FFA4-S signals through Gαq/11 and β-arrestin, while FFA4-L is intrinsically biased solely towards β-arrestin signaling. Recently, we and others have shown that phosphorylation of the FFA4 C-terminal tail is responsible for β-arrestin interactability and signaling. Given the significance of β-arrestin in the anti-inflammatory function of FFA4, the goal of this study was to examine the role of the C-terminal β-arrestin phosphosensor in FFA4 signaling induced by PMA and LPS in murine Raw 264.7 macrophages. Our data reveal for the first time that both FFA4 isoforms modulate PMA-induced ROS generation, and that abolishment of the FFA4-S, but not FFA4-L C-terminal phosphosensor, is detrimental to this effect. Furthermore, we show that while both isoforms reduce PMA-induced expression of COX-2, removal of the FFA4-S phosphosensor significantly decreases this response, suggesting that these effects of FFA4-S are β-arrestin mediated. On the contrary, FFA4-S, as well as the truncated C-terminal congener lacking the β-arrestin phosphosensor were both able to reduce LPS-induced NF-κB activity and ERK1/2 phosphorylation. However, FFA4-L and its corresponding mutant were incapable of modulating either, suggesting that these responses are mediated by G protein coupling. Taken together, our data reveal important structure-function and signaling differences between the two FFA4 isoforms, and for the first time link FFA4 to modulation of ROS in macrophages.

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Section: Methodssupporting

confidence: 89%

Free-fatty acid receptor-4 (FFA4) modulates ROS generation and COX-2 expression via the C-terminal β-arrestin phosphosensor in Raw 264.7 macrophages

Cheshmehkani

Senatorov

Dhuguru

et al. 2017

Biochemical Pharmacology

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“…440 N-tosylimines could also serve as electrophiles in this type of transformations. In this context, the groups of He 441 and Lu 442 independently reported an efficient preparation of 9-aminoxanthenes 6-10 from salicyl N-tosylimines 6-9 and arynes (Scheme 74d). Recently, Yoshida et al disclosed that the reaction between S-(2hydroxyaryl) 4-toluenethiosulfonates 6-11 (X = O) and osilylaryl triflates could furnish phenoxathiins 6-12 (X = O) (Scheme 74e).…”

Section: With O-nucleophilesmentioning

confidence: 99%

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

2021

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Arynes are among the most active organic intermediates and have found numerous applications in expeditious preparation of substituted arenes. In the past 20 years, chemists have witnessed a resurgence in aryne chemistry, which is mainly attributed by the extensive utilization of Kobayashi's method, a fluoride-induced removal of the TMS group with concomitant departure of its ortho OTf group on o-silylaryl triflates. Nowadays, o-silylaryl triflates are the most frequently employed aryne precursors. This review provides an overview of the history of Kobayashi's method, its methodological achievements, and its applications in the synthesis of natural products, bioactive molecules, and polycyclic aromatic hydrocarbons.

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“…HRMS (ESI + ): calcd for C 14 H 12 BrNNaO 3 S [M + Na] + , 375.9613; found, 375.9610. This compound is known …”

Section: Methodsmentioning

confidence: 99%

“…This compound is known. 15 (E)-N-(4-Fluoro-2-hydroxybenzylidene)-4-methylbenzenesulfonamide (1d). Brown solid (yield 97%, purity > 98%); 1 H NMR (400 MHz, CDCl 3 ): δ 11.17 (s, 1H), 9.05 (s, 1H), 7.85 (d, J = 8.2 Hz, 2H), 7.50 (dd, J = 8.4, 6.45 Hz, 1H), 7.36 (d, J = 8.0 Hz, 2H), 6.66− 6.76 (m, 2H), 2.45 (s, 3H).…”

Section: ■ Conclusionmentioning

confidence: 99%

Organocatalytic Asymmetric Domino Oxa-Michael–Mannich-[1,3]-Amino Rearrangement Reaction of N-Tosylsalicylimines to α,β-Unsaturated Aldehydes by Diarylprolinol Silyl Ethers

Wang

Huang

et al. 2019

J. Org. Chem.

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An organocatalytic asymmetric enantioselective domino oxa-Michael–Mannich-[1,3]-amino rearrangement reaction of N-tosylsalicylimines with a wide range of α,β-unsaturated aldehydes utilizing diarylprolinol silyl ether catalysis is described. The catalytic reactions proceed with excellent enantioselectivity (up to 99% ee) to produce the corresponding chair N-tosylimines-chromenes with a yield of up to 99%, tolerating a range of functional groups. This methodology offers a new method with great potential to further extend the synthetic power and versatility of chiral aminocatalysis.

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Efficient Synthesis of N-(9-Xanthyl)-4-Toluenesulfonamides Enabled by an Addition-Cyclization Cascade of Arynes

Abstract: An efficient synthesis of N-(9-xanthyl)-4-toluenesulfonamides is described in which salicyl N-tosylimines react with silylaryl triflates in the presence of CsF. This mild process involves an addition-cyclization cascade in which arynes are generated and trapped in situ.

Cited by 8 publications

References 2 publications

Free-fatty acid receptor-4 (FFA4) modulates ROS generation and COX-2 expression via the C-terminal β-arrestin phosphosensor in Raw 264.7 macrophages

Free-fatty acid receptor-4 (FFA4) modulates ROS generation and COX-2 expression via the C-terminal β-arrestin phosphosensor in Raw 264.7 macrophages

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

Organocatalytic Asymmetric Domino Oxa-Michael–Mannich-[1,3]-Amino Rearrangement Reaction of N-Tosylsalicylimines to α,β-Unsaturated Aldehydes by Diarylprolinol Silyl Ethers

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