Novel Trifluoromethylpyrazole Acyl Thiourea Derivatives: Synthesis, Antifungal Activity and Docking Study

Wang, Han; Zhai, Zhi-Wen; Shi, Yanhong; Tan, Cheng‐Xia; Weng, Jian‐Quan; Li, Han; Li, Baoju; Liu, Xinghai

doi:10.2174/1570180815666180704103047

Cited by 38 publications

(28 citation statements)

References 34 publications

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“…Docking scores (‐CDOCKER interaction energy) of the best‐fitted poses with the active site at the SDH structure were then recorded. The entire process was done in accordance with our previous work …”

Section: Fungicidal Activitymentioning

confidence: 99%

Novel 4‐pyrazole carboxamide derivatives containing flexible chain motif: design, synthesis and antifungal activity

Liu

Zhai

et al. 2019

Pest Management Science

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Background In recent years, carboxamide fungicides, targeting succinate dehydrogenase (SDH), have shown highly efficient and broad spectrum fungicidal activity. Structure–activity relationship (SAR) results for these commercial fungicides show that the carboxamide group was a key active group. This is useful information for the discovery of new pyrazole carboxamide derivatives with fungicidal activity. Results Twenty‐seven novel pyrazole carboxamides were designed and synthesized. Their fungicidal activities against Gibberella zeae, Phytophthora infestans, Phytophthora capsici, Rhizoctonia solani, Alternaria solani, Botrytis cinerea, Fusarium oxysporum, Cercospora arachidicola, Sclerotinia sclerotiorum and Physalospora piricola were tested; derivatives possessed excellent inhibitory at 50 mg L−1 in particular. Furthermore, some pyrazole carboxamides exhibited remarkably high activities against Sclerotinia sclerotiorum in vitro with EC50 values of 2.04 to 15.2 μg mL−1. In addition, some compounds also exhibited high activities against Physalospora piricola, Cercospora arachidicola and Phytophthora capsici. Inhibition activities against SDH proved that the designed analogues were effective at the enzyme level. The SAR of these pyrazole carboxamides was studied by using the docking method. Conclusion It is possible that pyrazole carboxamides, which exhibit good activity against Sclerotinia sclerotiorum, can be further optimized as a lead compounds of carboxamide fungicides. © 2019 Society of Chemical Industry

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Section: Fungicidal Activitymentioning

confidence: 99%

Novel 4‐pyrazole carboxamide derivatives containing flexible chain motif: design, synthesis and antifungal activity

Liu

Zhai

et al. 2019

Pest Management Science

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“…At physiological and organic levels, it rallies gas exchange, nutrient acquisition by root accommodation, and the recovery of the metabolism of sugar, subsequently increasing protein biosynthesis ( Arafa & Ibrahim, 2018 ). These derivatives play key role in therapies viz., antibacterial ( Venkatesh & Pandeya, 2009 ), anti-HIV ( Venkatachalam, Mao & Uckun, 2004 ), anti-inflammatory ( Keche et al, 2012 ), ligand and organocatalytic ( Arafa & Ibrahim, 2018 ; Kaya et al, 2015 ; Naz & Perveen, 2021 ) anticancer, antioxidant, antitubercular ( Zhao et al, 2013 ), and antifungal ( Wang et al, 2019 ). In addition, these compunds and their derivatives are also used in herbela or agro-products and also used in entonomogy for better growth and devlopment in eco-friendly insects.…”

Section: Introductionmentioning

confidence: 99%

Alleviation of drought stress by root-applied thiourea is related to elevated photosynthetic pigments, osmoprotectants, antioxidant enzymes, and tubers yield and suppressed oxidative stress in potatoes cultivars

Saleem

Wang

Parveen

et al. 2022

PeerJ

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The growth and productivity of plants are enhanced by the use of thiourea (TU) under stressful conditions. When TU is applied as a rooting medium, it improves plant growth characteristics and other physiological parameters in stressed environment. A pot experiment was conducted in the botanical garden of the Government College University, Faisalabad 38000, Pakistan to examine the TU-mediated fluctuations in some crucial physio-biochemical parameters and the oxidative defense of potatoes under a restricted water supply. For this purpose, two potato cultivars (potato-SH-5 and potato-FD-73) were sown in pots containing 10 kg of soil. Water was regularly applied to the pots until germination. After 2 weeks of germination, drought stress with 65% field capacity was imposed, while the control was subjected to 100% field capacity. TU, as a rooting medium, was applied at the vegetative stage (0 (no application), 0.5, 0.75 mM). A substantial reduction in the total number of leaves, leaf area, tuber biomass (fresh and dry weight), photosynthetic pigments, membrane permeability, and leaf relative water content (RWC) was recorded in plants under drought stress conditions as compared to control plants. The damaging eﬀects of water stress were more critical for cv. potato-FD-73 as compared to cv. potato-SH-5. In contrast, drought stress enhanced the malondialdehyde (MDA) and hydrogen peroxide (H2O2) content while also increased antioxidant enzyme activities (superoxide dismutase (SOD), peroxidase (POD), and catalase (CAT)) and triggered the accumulation of soluble proteins, soluble sugars, proline, and phenolic and anthocyanin contents. However, TU applied as rooting medium at 0.5 and 0.75 mM was eﬀective in reducing the detrimental eﬀects of water stress in both cultivars. Furthermore, increasing levels of TU enhanced chlorophyll pigments, dissolved proteins, complete dissolved sugars, and enzymatic capabilities of POD, SOD, and CAT, while reducing the MDA and H2O2 in both cultivars under stress conditions. In conclusion, TU improved the yield and chlorophyll pigments of potato plants by mitigating the adverse effects of drought stress through reduced EL, MDA, and H2O2 contents and improved activities of enzymatic and non-enzymatic antioxidants and osmoprotectants.

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“…In the last decades, thiourea derivatives have received considerable attention owing to their effective biological activities, including the antibacterial [1][2][3][4][5][6], antitubercular [7,8], antimalarial [9][10][11], antileishmanial [12], antifungal [13][14][15][16], or antiviral effects [17][18][19][20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

New Substituted Benzoylthiourea Derivatives: From Design to Antimicrobial Applications

et al. 2020

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The increasing threat of antimicrobial resistance to all currently available therapeutic agents has urged the development of novel antimicrobials. In this context, a series of new benzoylthiourea derivatives substituted with one or more fluorine atoms and with the trifluoromethyl group have been tested, synthesized, and characterized by IR, NMR, CHNS and crystal X-ray diffraction. The molecular docking has provided information regarding the binding affinity and the orientation of the new compounds to Escherichia coli DNA gyrase B. The docking score predicted the antimicrobial activity of the studied compounds, especially against E. coli, which was further demonstrated experimentally against planktonic and biofilm embedded bacterial and fungal cells. The compounds bearing one fluorine atom on the phenyl ring have shown the best antibacterial effect, while those with three fluorine atoms exhibited the most intensive antifungal activity. All tested compounds exhibited antibiofilm activity, correlated with the trifluoromethyl substituent, most favorable in para position.

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Novel Trifluoromethylpyrazole Acyl Thiourea Derivatives: Synthesis, Antifungal Activity and Docking Study

Cited by 38 publications

References 34 publications

Novel 4‐pyrazole carboxamide derivatives containing flexible chain motif: design, synthesis and antifungal activity

Novel 4‐pyrazole carboxamide derivatives containing flexible chain motif: design, synthesis and antifungal activity

Alleviation of drought stress by root-applied thiourea is related to elevated photosynthetic pigments, osmoprotectants, antioxidant enzymes, and tubers yield and suppressed oxidative stress in potatoes cultivars

New Substituted Benzoylthiourea Derivatives: From Design to Antimicrobial Applications

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