Design, synthesis, fungicidal activity and molecular docking studies of novel 2-((2-hydroxyphenyl)methylamino)acetamide derivatives

Tang, Zilong; Li, Xinxing; Yao, Yuan; Qi, Yongcun; Wang, Ming; Dai, Ningning; Wen, Yang; Wan, Yicong; Peng, Lifen

doi:10.1016/j.bmc.2019.03.040

Cited by 18 publications

(9 citation statements)

References 28 publications

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“…We have therefore changed the procedure and decided to use a convergent synthesis methodology: performing, on one hand, the acylation of various primary amine to form bromoacetamide intermediates and carry out the substitution reaction on the pyrrole 1 in the last step. The acylation of commercially available 2-bromoacetyl bromide was successfully carried out with 10 different amines using the experimental protocol reported in the literature ( Table 2 ) [ 20 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Anti-Trypanosoma cruzi Biological Evaluation of Novel 2-Nitropyrrole Derivatives

et al. 2022

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Human American trypanosomiasis, called Chagas disease, caused by T. cruzi protozoan infection, represents a major public health problem, with about 7000 annual deaths in Latin America. As part of the search for new and safe anti-Trypanosoma cruzi derivatives involving nitroheterocycles, we report herein the synthesis of ten 1-substituted 2-nitropyrrole compounds and their biological evaluation. After an optimization phase, a convergent synthesis methodology was used to obtain these new final compounds in two steps from the 2-nitropyrrole starting product. All the designed derivatives follow Lipinski’s rule of five. The cytotoxicity evaluation on CHO cells showed no significant cytotoxicity, except for compound 3 (CC50 = 24.3 µM). Compound 18 appeared to show activity against T. cruzi intracellular amastigotes form (EC50 = 3.6 ± 1.8 µM) and good selectivity over the vero host cells. Unfortunately, this compound 18 showed an insufficient maximum effect compared to the reference drug (nifurtimox). Whether longer duration treatments may eliminate all parasites remains to be explored.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Anti-Trypanosoma cruzi Biological Evaluation of Novel 2-Nitropyrrole Derivatives

et al. 2022

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“…Molecular docking studies indicated that SDH enzyme could be one of the potential action targets for compound 82. 118 The triphenylphosphonium (TPP)-conjugated boscalid analogue 83, which was reported by Wang et al only recently, exhibited enhanced fungicidal activity and broader spectra compared to boscalid. The action mechanism study revealed that 83 not only efficiently inhibited the activity of the SDH enzyme but also unleashed a burst of ROS, resulting in irreversible damage to the mitochondrial structure and function.…”

Section: Journal Ofmentioning

confidence: 87%

Comprehensive Overview of Carboxamide Derivatives as Succinate Dehydrogenase Inhibitors

Luo

Ning

2022

J. Agric. Food Chem.

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Up to now, a total of 24 succinate dehydrogenase inhibitors (SDHIs) fungicides have been commercialized, and SDHIs fungicides were also one of the most active fungicides developed in recent years. Carboxamide derivatives represented an important class of SDHIs with broad spectrum of antifungal activities. In this review, the development of carboxamide derivatives as SDHIs with great significances were summarized. In addition, the structure−activity relationships (SARs) of antifungal activities of carboxamide derivatives as SDHIs was also summarized based on the analysis of the structures of the commercial SDHIs and lead compounds. Moreover, the cause of resistance of SDHIs and some solutions were also introduced. Finally, the development trend of SDHIs fungicides was prospected. We hope this review will give a guide for the development of novel SDHIs fungicides in the future.

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“…SDHIs fungicides containing difluoromethyl substituted pyrazole substructure such as fluxapyroxad and benzovindiflupyr show a broad spectrum of excellent fungicidal activity. [ 22‐25 ] To solve the resistance and improve potency of strobilurin fungicides, here, we designed and synthesized a series of novel strobilurin derivatives containing a difluoromethyl pyrazole moiety with an active substructure splicing method (Figure 1). [ 26 ] All title compounds were characterized by 1 H NMR, 13 C NMR and HRMS.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Design, Synthesis, and Evaluation of Fungicidal Activity of Novel Pyrazole‐Containing Strobilurin Derivatives^†

Hao

Wang

et al. 2021

Chin. J. Chem.

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Drug design | Strobilurins | Biological activity | Structure-activity relationships |Cytochrome bc 1 complexIn searching for novel fungicidal leads, a series of pyrazole-containing strobilurins were rationally designed, synthesized and characterized. Bioassay indicated that compound I-7 displayed excellent fungicidal activity against a broad spectrum of plant pathogens such as Gibberella zeae, Rhizoctonia cerealis, Sclerotinia sclerotiorum, Phytophthora infestans, Physalospora piricola and Pellicularia sasakii with EC 50 of 0.16, 0.02, 0.72, 0.07, 0.77 and 0.65 μg/mL, respectively, which were 3-10 times more potent than the positive control azoxystrobin against the corresponding pathogens. Moreover, like azoxystrobin and kresoxim methyl, I-7, displayed excellent protective activity against P. sorghi. Molecular docking validated that I-7 and azoxystrobin would share a similar binding mode with cytochrome bc 1 complex. This study demonstrates that I-7 is a promising fungicidal candidate for further development.

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Design, synthesis, fungicidal activity and molecular docking studies of novel 2-((2-hydroxyphenyl)methylamino)acetamide derivatives

Cited by 18 publications

References 28 publications

Synthesis and Anti-Trypanosoma cruzi Biological Evaluation of Novel 2-Nitropyrrole Derivatives

Synthesis and Anti-Trypanosoma cruzi Biological Evaluation of Novel 2-Nitropyrrole Derivatives

Comprehensive Overview of Carboxamide Derivatives as Succinate Dehydrogenase Inhibitors

Design, Synthesis, and Evaluation of Fungicidal Activity of Novel Pyrazole‐Containing Strobilurin Derivatives^†

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Design, synthesis, fungicidal activity and molecular docking studies of novel 2-((2-hydroxyphenyl)methylamino)acetamide derivatives

Cited by 18 publications

References 28 publications

Synthesis and Anti-Trypanosoma cruzi Biological Evaluation of Novel 2-Nitropyrrole Derivatives

Synthesis and Anti-Trypanosoma cruzi Biological Evaluation of Novel 2-Nitropyrrole Derivatives

Comprehensive Overview of Carboxamide Derivatives as Succinate Dehydrogenase Inhibitors

Design, Synthesis, and Evaluation of Fungicidal Activity of Novel Pyrazole‐Containing Strobilurin Derivatives†

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Design, Synthesis, and Evaluation of Fungicidal Activity of Novel Pyrazole‐Containing Strobilurin Derivatives^†