Development of green and low-cost chiral oxidants for asymmetric catalytic hydroxylation of enals

Yang, Xiaoqun; Wang, Hongling; Jin, Zhichao; Robin, Yonggui

doi:10.1016/j.gresc.2021.05.002

Cited by 29 publications

(10 citation statements)

References 59 publications

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“…Due to our continuous interest in developing structurally novel molecules with agricultural activities, − we aimed to develop a novel fluorine-containing phenylpyridine scaffold with herbicidal activities by linking the trifluoromethylpyridine fragment with the halogen-substituted phenyl moiety of saflufenacil under the direction of the structural splicing strategy. Meanwhile, due to the wide range of biological activities of N -substituted amino derivatives (Figure B), − a side chain such as amide, urea, and thiourea would be installed on the phenylpyridine skeleton to modify the herbicidal activity.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Herbicidal Activity of Substituted 3-(Pyridin-2-yl)Phenylamino Derivatives

Chen,

Cai,

Zhang

et al. 2024

J. Agric. Food Chem.

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To discover protoporphyrinogen oxidase (PPO) inhibitors with robust herbicidal activity and crop safety, three types of substituted 3-(pyridin-2-yl)phenylamino derivatives bearing amide, urea, or thiourea as side chain were designed via structure splicing strategy. Postemergence herbicidal activity assessment of 33 newly prepared compounds revealed that many of our compounds such as 6a, 7b, and 8d exhibited superior herbicidal activities against broadleaf and monocotyledon weeds to commercial acifluorfen. In particular, compound 8d exhibited excellent herbicidal activities and high crop safety at a dosage range of 37.5−150 g ai/ha. PPO inhibitory studies supported our compounds as typical PPO inhibitors. Molecular docking studies revealed that compound 8d provided effective interactions with Nicotiana tabacum PPO (NtPPO) via diverse interaction models, such as π−π stacking and hydrogen bonds. Molecular dynamics (MD) simulation studies and degradation studies were also conducted to gain insight into the inhibitory mechanism. Our study indicates that compound 8d may be a candidate molecule for the development of novel herbicides.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Herbicidal Activity of Substituted 3-(Pyridin-2-yl)Phenylamino Derivatives

Chen,

Cai,

Zhang

et al. 2024

J. Agric. Food Chem.

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“…Built upon our interests in NHC‐catalyzed enantioselective preparations of chiral heterocycles [32–39], we envisioned to develop a novel chiral anti‐PVY agent from the chiral thiazide derivatives bearing axial chirality. Herein, we disclose the stereoselective preparation of a broad range of axially chiral thiazines and exploration of their antiviral biological activities (Figure 1C) [29, 40–45].…”

Section: Introductionmentioning

confidence: 99%

“…In stark contrast, the assessment of the axially chiral compounds in pharmaceutical and agrochemical development has long been overlooked [3], despite its significant potential in drug discovery revealed by recent progress [29][30][31]. Built upon our interests in NHC-catalyzed enantioselective preparations of chiral heterocycles [32][33][34][35][36][37][38][39], we envisioned to develop a novel chiral anti-PVY agent from the chiral thiazide derivatives bearing axial chirality. Herein, we disclose the stereoselective preparation of a broad range of axially chiral thiazines and exploration of their antiviral biological activities (Figure 1C) [29,[40][41][42][43][44][45].…”

Section: Introductionmentioning

confidence: 99%

Design, enantioselective synthesis, and antiviral activities against potato virus Y of axially chiral thiazine derivatives

Shen,

Jin,

Song

et al. 2023

Journal of Heterocyclic Chem

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A series of novel thiazine derivatives featuring axial chirality in both (R) and (S) configurations were successfully synthesized by N‐heterocyclic carbene (NHC)‐catalyzed enantioselective [3 + 3] annulations, and their potential as anti‐plant virus agents against potato virus Y (PVY) was evaluated. Biological activity results demonstrated that most of these chiral thiazine derivatives exhibited significant activities against PVY. Notably, compound (S)‐3g displayed a remarkable 58% inactivation effect against PVY at a concentration of 500 μg/mL, slightly surpassing the effectiveness of Ningnanmycin (NNM) at 57%. Additionally, (S)‐3g exhibited curative activity of 57%, which is superior to NNM (53%). Molecular docking studies revealed preliminary insights into the distinct biological properties of the two different enantiomers, (R) or (S)‐3g against PVY, wherein single enantiomer (S)‐3g formed a more stable interaction with PVY‐CP, as indicated by its lower binding free energy (−41.18 kcal/mol) compared to (R)‐3g (−36.9 kcal/mol). The findings in this study with a new class of axially chiral thiazine derivatives shall inspire further development of chiral heterocycles as potential drug candidates for the protection of plant virus infections.

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“…N -Heterocyclic carbene (NHC) organocatalysis has seen dramatic development in the last couple of decades. − It can promote a variety of C–S bond formation reactions through diverse catalytic processes in both nonchiral and enantioselective fashions. Although comprehensive reviews have been documented focusing on metal-catalyzed − and organocatalyzed , C–S bond formation reactions, there is no review focusing on this type of reaction promoted by NHC organic catalysts.…”

Section: Introductionmentioning

confidence: 99%

N-Heterocyclic Carbene-Mediated Carbon–Sulfur Bond-Forming Reactions

Jin

Wang

et al. 2022

ACS Sustainable Chem. Eng.

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The carbon–sulfur (C–S) bond formation reactions enabled by N-heterocyclic carbene (NHC) organocatalysis are systematically summarized in this review. Diverse transformations involving NHC-catalyzed S-esterification, NHC-catalyzed nucleophilic S-conjugate addition, NHC-catalyzed S-addition reactions with electrophiles, and C–S bond formations via cooperative NHC/transition metal-catalyzed radical reactions are introduced and discussed. Our own comprehension and perspectives on this highly active research field are also provided at the end of this review.

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Development of green and low-cost chiral oxidants for asymmetric catalytic hydroxylation of enals

Cited by 29 publications

References 59 publications

Design, Synthesis, and Herbicidal Activity of Substituted 3-(Pyridin-2-yl)Phenylamino Derivatives

Design, Synthesis, and Herbicidal Activity of Substituted 3-(Pyridin-2-yl)Phenylamino Derivatives

Design, enantioselective synthesis, and antiviral activities against potato virus Y of axially chiral thiazine derivatives

N-Heterocyclic Carbene-Mediated Carbon–Sulfur Bond-Forming Reactions

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