One‐pot synthesis of anilides, herbicidal activity and molecular docking study

Sartori, Suélen K.; Alvarenga, Elson S.; Franco, Cristiane A; Ramos, Danielle S; Oliveira, Denilson F.

doi:10.1002/ps.4855

Cited by 13 publications

(3 citation statements)

References 60 publications

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“…Based on molecular docking, a series of p -hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors have been designed and synthesized, and the synthesized compounds were shown to be potential candidates for novel herbicides [19,20]. Anilides were synthesized through simple methods by Sartori et al [21], and the herbicidal activities of the anilides were evaluated. An in silico study was performed on anilides with herbicidal activity, and histone deacetylase was suggested to be the target enzyme for the activity of anilides in plants.…”

Section: Introductionmentioning

confidence: 99%

Protective Responses Induced by Chiral 3-Dichloroacetyl Oxazolidine Safeners in Maize (Zea mays L.) and the Detoxification Mechanism

et al. 2019

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Herbicide safeners selectively protect crops from herbicide injury while maintaining the herbicidal effect on the target weed. To some extent, the detoxification of herbicides is related to the effect of herbicide safeners on the level and activity of herbicide target enzymes. In this work, the expression of the detoxifying enzyme glutathione S-transferase (GST) and antioxidant enzyme activities in maize seedlings were studied in the presence of three potential herbicide safeners: 3-dichloroacetyl oxazolidine and its two optical isomers. Further, the protective effect of chiral herbicide safeners on detoxifying chlorsulfuron in maize was evaluated. All safeners increased the expression levels of herbicide detoxifying enzymes, including GST, catalase (CAT), and peroxidase (POD) to reduce sulfonylurea herbicide phytotoxicity in maize seedlings. Our results indicate that the R-isomer of 3-(dichloroacetyl)-2,2,5-trimethyl-1,3-oxazolidine can induce glutathione (GSH) production, GST activity, and the ability of GST to react with the substrate 1-chloro-2,4-dinitrobenzene (CDNB) in maize, meaning that the R-isomer can protect maize from damage by chlorsulfuron. Information about antioxidative enzyme activity was obtained to determine the role of chiral safeners in overcoming the oxidative stress in maize attributed to herbicides. The interaction of safeners and active target sites of acetolactate synthase (ALS) was demonstrated by molecular docking modeling, which indicated that both isomers could form a good interaction with ALS. Our findings suggest that the detoxification mechanism of chiral safeners might involve the induction of the activity of herbicide detoxifying enzymes as well as the completion of the target active site between the safener and chlorsulfuron.

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Section: Introductionmentioning

confidence: 99%

Protective Responses Induced by Chiral 3-Dichloroacetyl Oxazolidine Safeners in Maize (Zea mays L.) and the Detoxification Mechanism

et al. 2019

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“…The pre- and post-emergence herbicidal activities of the title compounds were evaluated at an application rate of 90 g ai/ha in a greenhouse according to a reported method [35,36]. Nine seeds of these plants ( A. retroflexus seeds, B. campestris seeds or D. sanguinalis seeds) were sown at a depth of 5 mm in a mixture of vermiculite/nutrient-enriched soil (1:1, m/m) with some water at 4 cm below the surface and then cultivated at 20–25 °C.…”

Section: Methodsmentioning

confidence: 99%

Design and Synthesis of N-phenyl Phthalimides as Potent Protoporphyrinogen Oxidase Inhibitors

Wei

Ren

et al. 2019

Molecules

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Protoporphyrinogen oxidase (PPO) has been identified as one of the most promising targets for herbicide discovery. A series of novel phthalimide derivatives were designed by molecular docking studies targeting the crystal structure of mitochondrial PPO from tobacco (mtPPO, PDB: 1SEZ) by using Flumioxazin as a lead, after which the derivatives were synthesized and characterized, and their herbicidal activities were subsequently evaluated. The herbicidal bioassay results showed that compounds such as 3a (2-(4-bromo-2,6-difluorophenyl) isoindoline-1,3-dione), 3d (methyl 2-(4-chloro-1,3-dioxoisoindolin-2-yl)-5-fluorobenzoate), 3g (4-chloro-2-(5-methylisoxazol-3-yl) isoindoline-1,3-dione), 3j (4-chloro-2-(thiophen-2-ylmethyl) isoindoline-1,3-dione) and 3r (2-(4-bromo-2,6-difluorophenyl)-4-fluoroisoindoline-1,3-dione) had good herbicidal activities; among them, 3a showed excellent herbicidal efficacy against A. retroflexus and B. campestris via the small cup method and via pre-emergence and post-emergence spray treatments. The efficacy was comparable to that of the commercial herbicides Flumioxazin, Atrazine, and Chlortoluron. Further, the enzyme activity assay results suggest that the mode of action of compound 3a involves the inhibition of the PPO enzyme, and 3a showed better inhibitory activity against PPO than did Flumioxazin. These results indicate that our molecular design strategy contributes to the development of novel promising PPO inhibitors.

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“…Therefore, diarylamines as easily available substrates have proven a convenient choice for construction of structural diversity molecules with promising bioactivity. In addition, carboxamides are also a useful class of molecules with potential pharmacological ( Odingo et al, 2017 ; Tang et al, 2018 ; Barker et al, 2019 ; Ling et al, 2019 ; Sethy et al, 2019 ; Sun et al, 2019 ; Yang et al, 2019 ) and agroactive activities ( Sartori et al, 2018 ; Tsikolia et al, 2018 ; Yu et al, 2018 ; Liu et al, 2019 ; Siber et al, 2019 ; Tsikolia et al, 2019 ; Liu et al, 2020 ), and many carboxamides have been developed as clinical drugs or agrochemicals, which demonstrate that amide units will play an important role in the development of drugs and pesticides.…”

Section: Introductionmentioning

confidence: 99%

Diarylamine-Guided Carboxamide Derivatives: Synthesis, Biological Evaluation, and Potential Mechanism of Action

Huang

Zhang

et al. 2022

Front. Chem.

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Diarylamines are a class of important skeleton widely existing in drugs or natural products. To discover novel diarylamine analogues as potential drugs, two series of diamide and carboxamide derivatives containing diarylamine scaffold were designed, synthesized and evaluated for their potential cytotoxic activities. The bioassay results indicated that some of the obtained compounds (C5, C6, C7, C11) exhibited good cytotoxic effect on cancer cell lines (SGC-7901, A875, HepG2), especially, compound C11 present significantly selective proliferation inhibition activity on cancer and normal cell lines (MARC145). In addition, the possible apoptosis induction for highly potential molecules was investigated, which present compound C11 could be used as novel lead compound for discovery of promising anticancer agents.

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One‐pot synthesis of anilides, herbicidal activity and molecular docking study

Abstract: Anilides 4d, 4e, 4 g, and 4 h are promising candidates for the development of novel herbicides. According to in silico studies, they inhibit histone deacetylase in plants, which can be exploited for the development of new weed control methods. © 2018 Society of Chemical Industry.

Cited by 13 publications

References 60 publications

Protective Responses Induced by Chiral 3-Dichloroacetyl Oxazolidine Safeners in Maize (Zea mays L.) and the Detoxification Mechanism

Protective Responses Induced by Chiral 3-Dichloroacetyl Oxazolidine Safeners in Maize (Zea mays L.) and the Detoxification Mechanism

Design and Synthesis of N-phenyl Phthalimides as Potent Protoporphyrinogen Oxidase Inhibitors

Diarylamine-Guided Carboxamide Derivatives: Synthesis, Biological Evaluation, and Potential Mechanism of Action

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