Shuai Zhang

Hubei University of Technology

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Shu‐Ping Luo

Zhejiang University of Technology

Liang Yin

Shanghai Institute of Organic Chemistry

Jun‐Zhao Xiao

Shanghai Institute of Organic Chemistry

Zhenyuan Xu

Zhejiang University of Technology

Dan‐Qian Xu

Zhejiang University of Technology

Baoquan Chen

Tianjin University of Technology

Yanbo Li

University of Chinese Academy of Sciences

Rui Tang

Dalian Medical University

Yu‐Ming Liu

Tianjin University of Technology

Yi-Feng Wang

Zhejiang University of Technology

Cooperative Institutions

Chinese Academy of Sciences

University of Chinese Academy of Sciences

Tianjin University of Technology

Zhejiang University of Technology

Tianjin University of Science and Technology

Shanghai Institute of Organic Chemistry

China International Science and Technology Cooperation

Tsinghua University

Qingdao University of Science and Technology

Guilin University of Technology

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Base-Controlled Divergent Synthesis of 5-Cyanobenzoxepines and Benzofuro[2,3-b]pyridines from 2-Bromophenylacetonitriles and Ynones

Organic Letters (2019)

Lulu Chen Jingwen Zhang Pei Chen Shuai Zhang Wan-Wan Yang

An effective base-controlled divergent annulation reaction of 2-bromophenylacetonitriles and ynones has been developed. Various functionalized 5-cyanobenzoxepines and benzofuro[2,3-b]pyridines were obtained with a broad substrate scope and high regioselectivity in moderate to excellent yield. Of importance, an unexpected O-rearrangement reaction to access benzofuro[2,3-b]pyridines was observed using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the base, and the possible mechanism was supported by 18O-labeled experiments. In addition, the gram-scale synthesis and further transformation of the product were studied.

Annulation

Base (topology)

Scope (computer science)

10.1021/acs.orglett.9b01700

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Citations (28)

Copper(I)‐Catalyzed Asymmetric Synthesis of P‐Chiral Aminophosphinites

Angewandte Chemie International Edition (2022)

Yanbo Li Hu Tian Shuai Zhang Jun‐Zhao Xiao Liang Yin

Herein, a copper(I)-catalyzed reaction of diarylphosphines and O-benzoyl hydroxylamines is developed. In the cases of symmetrical diarylphosphines, a series of aminophosphinites is prepared in high yields. In the cases of unsymmetrical diarylphosphines, an array of P-chiral aminophosphinites is synthesized in high yields with high enantioselectivity by using a copper(I)-(R,RP )-Ph-FOXAP complex as a chiral catalyst. Based on several control experiments and 31 P NMR studies, a two-electron redox mechanism involving the dynamic kinetic asymmetric transformation of unsymmetrical diarylphosphines is proposed for the copper(I)-catalyzed asymmetric reaction. Finally, one representative P-chiral phosphoric amide generated through the oxidation with H2 O2 is transformed to a chiral diarylphosphinate in high yield with retained enantioselectivity, which allows further transformations towards various P-chiral tertiary phosphines.

Amide

10.1002/anie.202117760

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Citations (25)

Copper(I)‐Catalyzed Asymmetric Synthesis of P‐Chiral Aminophosphinites

Angewandte Chemie (2022)

Yanbo Li Hu Tian Shuai Zhang Jun‐Zhao Xiao Liang Yin

Abstract Herein, a copper(I)‐catalyzed reaction of diarylphosphines and O ‐benzoyl hydroxylamines is developed. In the cases of symmetrical diarylphosphines, a series of aminophosphinites is prepared in high yields. In the cases of unsymmetrical diarylphosphines, an array of P ‐chiral aminophosphinites is synthesized in high yields with high enantioselectivity by using a copper(I)‐( R , R P )‐Ph‐FOXAP complex as a chiral catalyst. Based on several control experiments and 31 P NMR studies, a two‐electron redox mechanism involving the dynamic kinetic asymmetric transformation of unsymmetrical diarylphosphines is proposed for the copper(I)‐catalyzed asymmetric reaction. Finally, one representative P ‐chiral phosphoric amide generated through the oxidation with H 2 O 2 is transformed to a chiral diarylphosphinate in high yield with retained enantioselectivity, which allows further transformations towards various P ‐chiral tertiary phosphines.

Amide

10.1002/ange.202117760

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Citations (1)

Chemoenzymatic synthesis of sialyl-α2,3-lactoside–functionalized BSA conjugate inhibits influenza infection

European Journal of Medicinal Chemistry (2024)

Mingming Xue Lintongqing Tan Shuai Zhang Jianing Wang Xue Mi

Conjugate

10.1016/j.ejmech.2024.116633

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Citations (1)

(2R,5S)-5-Benzyl-2,3-dimethyl-4-oxo-2-phenylimidazolidin-1-ium chloride

Acta Crystallographica Section E Structure Reports Online (2009)

Shuai Zhang Yi-Feng Wang Bailin Li Guangcun Zhang Shu‐Ping Luo

The title hydrochloride salt, C18H21N2O+·Cl−, is an imidazolidinone catalyst, which was derived from L-phenylalanine through cyclization with acetophenone. The imidazolidinone compound has a five-membered heterocyclic ring including two chiral centres. The imidazolidinone ring displays an envelope conformation, with the flap protonated N atom lying 0.497 (3) Å above the mean plane of the remaining four atoms. In the crystal structure, one-dimensional supramolecular chains parallel to the crystallographic 21 screw axis are formed by N—H⋯Cl hydrogen bonds involving the NH2+ and Cl− groups. Intramolecular N—H⋯Cl interactions are also present.

Acetophenone

10.1107/s1600536809010460

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Citations (1)

Facile protection of carbonyl compounds as oxathiolanes and thioacetals promoted by PEG1000-based dicationic acidic ionic liquid as chemoselective and recyclable catalyst

Journal of Molecular Liquids (2014)

Yiming Ren Juan‐Juan Shao Zhi‐Chuan Wu Shuai Zhang Tingxian Tao

10.1016/j.molliq.2014.04.020

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Citations (9)

Synthesis and pharmacological evaluation of new disulfides linked to 1,2,4-triazole bearing urea moiety

Medicinal Chemistry Research (2023)

Rui Tang Haichuan Zhao Shuai Zhang Xiaojia Liu Jin‐Biao Liu

Moiety

HeLa

IC50

Sulfanyl

Triazole

Lead compound

1,2,4-Triazole

1,2,3-Triazole

10.1007/s00044-023-03100-3

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Citations (1)

Copper-Catalyzed Sulfonylation Reaction of NH-Sulfoximines with Aryldiazonium Tetrafluoroborates and Sulfur Dioxide: Formation of N-Sulfonyl Sulfoximines

The Journal of Organic Chemistry (2023)

Hongsheng Nie Zhicheng Xiong Meiqian Hu Shuai Zhang Changsheng Qin

An efficient and practical SO2 insertion protocol of NH-sulfoximines with aryldiazonium tetrafluoroborates and DABSO toward N-sulfonyl sulfoximines has been developed under mildly basic conditions. This transformation features easy operation, readily available substrates, and mild conditions. A tentative mechanism is proposed, which indicates that the aryldiazonium tetrafluoroborates would be radical donors under standard reaction conditions. The aryl radical produced in situ from diazonium salts would be trapped by SO2 to generate an arylsulfonyl radical and then undergo further transformation to generate the final N-sulfonyl sulfoximines.

Sulfonyl

10.1021/acs.joc.2c02742

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Citations (4)

Improving Winter Wheat Yield Forecasting Based on Multi-Source Data and Machine Learning

Agriculture (2022)

Yuexia Sun Shuai Zhang Fulu Tao Rashad Aboelenein Alia Amer

To meet the challenges of climate change, population growth, and an increasing food demand, an accurate, timely and dynamic yield estimation of regional and global crop yield is critical to food trade and policy-making. In this study, a machine learning method (Random Forest, RF) was used to estimate winter wheat yield in China from 2014 to 2018 by integrating satellite data, climate data, and geographic information. The results show that the yield estimation accuracy of RF is higher than that of the multiple linear regression method. The yield estimation accuracy can be significantly improved by using climate data and geographic information. According to the model results, the estimation accuracy of winter wheat yield increases dramatically and then flattens out over months; it approached the maximum in March, with R2 and RMSE reaching 0.87 and 488.59 kg/ha, respectively; this model can achieve a better yield forecasting at a large scale two months in advance.

10.3390/agriculture12050571

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Citations (19)

SUMO E1 covalent allosteric inhibitors modulate polyamine synthesis via the MAT2A-AdoMetDC axis

bioRxiv (Cold Spring Harbor Laboratory) (2024)

Shuai Zhang Zhiying Wang Yubing Jiao Xiaoyu Shi Yuanbao Ai

Upregulation of protein SUMOylation is associated with various diseases, and SUMOylation inhibitors are promising drug candidates. We performed the first virtual screening of SUMO E1 covalent allosteric inhibitors (CAIs) and identified two SUMO E1 CAIs with new scaffolds and covalent warheads. We further demonstrated that these new CAIs perturbed the SUMOylation pathway and protein SUMOylation. Specifically, these CAIs affected the SUMOylation of the methionine adenosyltransferases MAT2A. The inhibition of MAT2A SUMOylation unexpectedly stimulated polyamine synthesis. Lastly, we showed that the combination of SUMO E1 CAIs with a polyamine synthesis inhibitor had synergistic effects in inhibiting T47D cells. Our work demonstrated the first cost-effective virtual screening of SUMO E1 CAIs, found that the downregulation of MAT2A SUMOylation increases polyamine synthesis, and SUMO E1 CAIs can synergize with polyamine synthesis inhibitors. This work would be of great value to the study of SUMOylation, covalent/allosteric drugs, and the polyamine metabolism network.

Polyamine

10.1101/2024.12.12.627095

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Citations (0)