Efficient synthesis of benzosultams containing continuous quaternary carbons <i>via</i> trapping active ylides with cyclic <i>N</i>-sulfonyl ketimines

Luo, Zhengli; Chen, Xuwen; Xue, Jian; Deng, Yaqi; Shen, Dong; Liu, Shunying

doi:10.1039/d2qo01409b

Cited by 3 publications

(1 citation statement)

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“…9 Molecules with continuous quaternary carbon centers commonly exhibit good physical and chemical properties, and biological activities. 10,11 Many elegant approaches have been reported with the purpose of building quaternary carbon centers. 12,13 However, anchoring continuous quaternary carbon centers to an isoindolinone scaffold has seldom been investigated, which may be due to the great challenge resulting from the steric hindrance effect.…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis of bioactive isoindolinone derivatives containing continuous quaternary carbons by intermolecular OH transfer

He,

Li,

Song

et al. 2024

New J. Chem.

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Section: Introductionmentioning

confidence: 99%

Efficient synthesis of bioactive isoindolinone derivatives containing continuous quaternary carbons by intermolecular OH transfer

He,

Li,

Song

et al. 2024

New J. Chem.

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One-Pot Synthesis of Polycyclic Sultams Enabled by Gold-Catalyzed Hydroamination of o-Alkynylbenzenesulfonamides and Subsequent Iodine(III)-Mediated Counteranion-Assisted Intramolecular Annulation

Zhang,

Song

2024

Org. Lett.

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Herein we present a facile and efficient one-pot synthetic protocol for the construction of polycyclic sultams. This protocol involves gold-catalyzed intramolecular hydroamination of o-alkynylbenzenesulfonamides followed by HTIB-mediated counteranion-assisted intramolecular annulation. The transformation tolerates a wide range of functional groups, resulting in the formation of highly functionalized and valuable polycyclic sultam skeletons in moderate to excellent yields. These polycyclic sultams are widely used as key building blocks in organic science.

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Novel Alkynylamide-Based Nonpeptidic Allosteric Inhibitors for SARS-CoV-2 3-Chymotrypsin-like Protease

Xue,

Li,

Wang

et al. 2024

ACS Pharmacol. Transl. Sci.

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Although the coronavirus disease 2019 (COVID-19) crisis has passed, there remains a necessity for continuous efforts toward developing more targeted drugs and preparing for potential future virus attacks. Currently, most of the drugs received authorization for the treatment of COVID-19 have exhibited several limitations, such as poor metabolic stability, formidable preparation, and uncertain effectiveness. It is still significant to develop novel, structurally diverse small-molecule antiviral drugs targeting SARS-CoV-2 3-chymotrypsin-like protease (3CL pro ). Herein, we report a class of alkynylamide-based nonpeptidic 3CL pro inhibitors that can be prepared conveniently by our previously developed one-pot synthetic method. The structure−activity relationships of alkynylamides as SARS-CoV-2 3CL pro inhibitors have been carefully investigated and discussed in this study. The two stereoisomers of the resulting molecules exhibit stereoselective interaction with 3CL pro , and the optimized compound (S,R)-4y inhibits 3CL pro with high potency (IC 50 = 0.43 μM), low cytotoxicity, and acceptable cell permeability. Compound (S,R)-4y presents as a noncovalent inhibitor of 3CL pro against SARS-CoV-2 by the time-dependent inhibition assay (TDI) and mass spectrometry analysis. The Lineweaver−Burk plots, binding energy, surface plasmon resonance, and molecular docking studies suggest that (S,R)-4y specifically binds to an allosteric pocket of the SARS-CoV-2 3CL pro . These findings provide a novel class of nonpeptidic alkynylamide-based allosteric inhibitors with high selectivity against SARS-CoV-2 3CL pro featured by a simplified one-pot synthesis at room temperature in air.

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Efficient synthesis of benzosultams containing continuous quaternary carbons via trapping active ylides with cyclic N-sulfonyl ketimines

Abstract: A rapid and efficient method for the synthesis of benzosultams containing continuous quaternary carbons has been developed moderate to excellent yields at room temperature in air with a one-pot fashion....

Cited by 3 publications

References 49 publications

Efficient synthesis of bioactive isoindolinone derivatives containing continuous quaternary carbons by intermolecular OH transfer

Efficient synthesis of bioactive isoindolinone derivatives containing continuous quaternary carbons by intermolecular OH transfer

One-Pot Synthesis of Polycyclic Sultams Enabled by Gold-Catalyzed Hydroamination of o-Alkynylbenzenesulfonamides and Subsequent Iodine(III)-Mediated Counteranion-Assisted Intramolecular Annulation

Novel Alkynylamide-Based Nonpeptidic Allosteric Inhibitors for SARS-CoV-2 3-Chymotrypsin-like Protease

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