Design, synthesis, DNA assessment and molecular docking study of novel 2-(pyridin-2-ylimino)thiazolidin-4-one derivatives as potent antifungal agents

Metwally, Nadia H.; Radwan, Ibrahim Taha; El-Serwy, Walaa S.; Mohamed, Mohamed Ahmed

doi:10.1016/j.bioorg.2018.11.050

Cited by 33 publications

(18 citation statements)

References 26 publications

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“…Until recently, different management strategies have been applied to reduce Fusarium root rot and wilt disease incidence. For example, organic control, resistant varieties, crop rotation, and soil solarization [8]. Cu-based biocides are considered the most effective compounds against Fusarium diseases like wilt and root rot [9].…”

Section: Introductionmentioning

confidence: 99%

Reduced Graphene Oxide Nanosheet-Decorated Copper Oxide Nanoparticles: A Potent Antifungal Nanocomposite against Fusarium Root Rot and Wilt Diseases of Tomato and Pepper Plants

et al. 2020

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Sustainable use of nanotechnology in crop protection requires an understanding of the plant’s life cycle, potential toxicological impacts of nanomaterials and their mechanism of action against the target pathogens. Herein, we show some properties of a candidate antifungal nanocomposite made from copper oxide (CuO; otherwise an essential soil nutrient) nanoparticles (NPs), with definite size and shape, decorating the surface of reduced graphene oxide (rGO) nanosheets. The successful preparation of the rGO-CuO NPs was confirmed by spectroscopic and microscopic analyses, and its antifungal activity against wild strains of Fusarium oxysporum affecting tomato and pepper plants was successfully confirmed. A comparative analysis in vitro indicated that this nanocomposite had higher antifungal activity at only 1 mg/L than the conventional fungicide Kocide 2000 at 2.5 g/L. Further investigation suggested that rGO-CuO NPs creates pits and pores on the fungal cell membranes inducing cell death. In planta results indicated that only 1 mg/L from the nanocomposite is required to reduce Fusarium wilt and root rot diseases severity below 5% for tomato and pepper plants without any phytotoxicity for about 70 days. Comparatively, 2.5 g/L of Kocide 2000 are required to achieve about 30% disease reduction in both plants. The present study contributes to the concept of agro-nanotechnology, showing the properties of a novel ecofriendly and economic nanopesticide for sustainable plant protection.

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Section: Introductionmentioning

confidence: 99%

Reduced Graphene Oxide Nanosheet-Decorated Copper Oxide Nanoparticles: A Potent Antifungal Nanocomposite against Fusarium Root Rot and Wilt Diseases of Tomato and Pepper Plants

et al. 2020

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“…A mixture of DABCO (0.224 g, 2.0 mmol) and 2,3-dichloro-1-propanol (0.129 g, 1.0 mmol) in EtOH (15.0 ml) was sonicated for 1 h (TLC). The solvent was removed under reduced pressure to give derivative (2). Then, NaBF 4 (0.22 g, 2.0 mmol) or NaOAc (0.164 g, 2.0 mmol) was added to the residue of 2 in EtOH (15.0 ml).…”

Section: Synthesis Of the Catalysts Bis-dil (3ab)mentioning

confidence: 99%

New dicationic DABCO-based ionic liquids: a scalable metal-free one-pot synthesis of bis-2-amino-5-arylidenethiazol-4-ones

Arafa

Mourad

2019

R. Soc. open sci.

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Herein, a novel DABCO-based dicationic ionic liquid (bis-DIL) was easily prepared from the sonication of DABCO with 1,3-dichloro-2-propanol and then characterized by several techniques. Thereafter, under the ultimate green conditions, the performance of the bis-DIL was examined for the sono-synthesis of a new library of bis-2-amino-5-arylidenethiazol-4-ones via one-pot pseudo-five-component Knoevenagel condensation reaction of appropriate dialdehydes, rhodanine and amines. This protocol is tolerant towards several mono- and dialdehydes, excellently high yielding and affording access to the desired products in a single step within a short reaction time. Compared with the conventional methodologies, the proposed method displayed several remarkable merits such as milder reaction conditions without any side product, green solvent media, recording well in a variety of green metrics and applicability in gram-scale production. The recyclability of the bis-DIL was also investigated with an average recovered yield of 97% for six sequential cycles without any significant loss of the activity.

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“…Compounds with a 2‐imino‐thiazolidin‐4‐one scaffold have attracted much attention over the years, due to wide broad‐spectrum pharmacological properties such as antimicrobial, [ 13 ] anti‐malarial, [ 14 ] anti‐HIV, [ 15 ] anti‐inflammatory, [ 16 ] antioxidant, [ 17 ] and MAO‐A and MAO‐B inhibitory activities. [ 18 ] Besides this, compounds containing a pyridyl structure are well known to possess a wide range of biological and pharmacological activities.…”

Section: Introductionmentioning

confidence: 99%

Three ‐(pyridin‐2‐yl)‐2‐(pyridin‐2‐ylimino)thiazolidin‐4‐one as a novel inhibitor of cerebral MAO‐B activity with antioxidant properties and low toxicity potential

Carraro

Alves

Rech

et al. 2021

J Biochem & Molecular Tox

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Some brain diseases are associated with oxidative stress and altered monoamine oxidase (MAO) activity. The objective of this study was to evaluate the antioxidant and neuroprotective actions through MAO inhibition of 3‐(pyridin‐2‐yl)‐2‐(pyridine‐2‐ylimino) thiazolidin‐4‐one (PPIT, a synthetic molecule containing a thiazolidinone nucleus), as well as its effects on toxicity parameters in Swiss female mice. Five in vitro assays were carried out to verify the PPIT antioxidant capacity: protein carbonylation (PC), 2,2'‐azino‐bis(3‐ethylbenzothiazoline‐6‐sulfonic acid) (ABTS), 1,1‐diphenyl‐2‐picryl‐hydrazil (DPPH), ferric ion (Fe3+) reducing antioxidant power (FRAP), and superoxide dismutase (SOD)‐like activity. The results showed that PPIT reduced the level of PC in the homogenate of the brain. This compound did not demonstrate SOD mimetic activity, but it acted as a free radical scavenger (ABTS and DPPH) and exhibited reducing activity in the FRAP assay. In addition, the effects of PPIT on cerebral MAO activity (MAO‐A and B isoforms) were investigated in vitro. Our data revealed inhibition of the MAO‐B activity by PPIT with no effects on MAO‐A. Lastly, an acute oral toxicity test was conducted in mice. No changes in food intake, body weight, and biochemical markers of kidney and liver damage were detected in mice treated with a high dose of PPIT (300 mg/kg). In conclusion, the present study demonstrated that PPIT exhibits antioxidant activity and selectively inhibits the MAO‐B isoform without causing apparent toxicity. These findings suggest PPIT as a potential therapeutic candidate to be tested in preclinical models of brain diseases involving perturbations of MAO‐B activity and redox status.

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Design, synthesis, DNA assessment and molecular docking study of novel 2-(pyridin-2-ylimino)thiazolidin-4-one derivatives as potent antifungal agents

Cited by 33 publications

References 26 publications

Reduced Graphene Oxide Nanosheet-Decorated Copper Oxide Nanoparticles: A Potent Antifungal Nanocomposite against Fusarium Root Rot and Wilt Diseases of Tomato and Pepper Plants

Reduced Graphene Oxide Nanosheet-Decorated Copper Oxide Nanoparticles: A Potent Antifungal Nanocomposite against Fusarium Root Rot and Wilt Diseases of Tomato and Pepper Plants

New dicationic DABCO-based ionic liquids: a scalable metal-free one-pot synthesis of bis-2-amino-5-arylidenethiazol-4-ones

Three ‐(pyridin‐2‐yl)‐2‐(pyridin‐2‐ylimino)thiazolidin‐4‐one as a novel inhibitor of cerebral MAO‐B activity with antioxidant properties and low toxicity potential

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