Design, synthesis and biological evaluation of novel nicotinamide derivatives bearing a substituted pyrazole moiety as potential <scp>SDH</scp> inhibitors

Lv, XianâHai; Ren, Zi-Li; Liu, Peng; Li, BingâXin; Li, QingâShan; Chu, MingâJie; Cao, HaiâQun

doi:10.1002/ps.4488

Cited by 34 publications

(41 citation statements)

References 28 publications

(35 reference statements)

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“…The fungicidal activities were investigated with three plant parasitic fungi ( Alternaria alternata , Botrytis cinerea , and Fusarium oxysporum ), and mycelial inhibition of radial growth on PDA media was employed [ 22 , 23 ].…”

Section: Methodsmentioning

confidence: 99%

Promising Fungicides from Allelochemicals: Synthesis of Umbelliferone Derivatives and Their Structure–Activity Relationships

et al. 2018

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Umbelliferone was discovered to be an important allelochemical in our previous study, but the contribution of its activity and structure has not yet been revealed. In this study, a series of analogues were synthesized to determine the skeleton of umbelliferone and examine its fungicidal activity. Furthermore, targeted modifications were conducted with three plant parasitic fungi to examine the lead compounds. Among those tested, compounds 2f and 10 were found to show excellent antifungal activity with an inhibitory rate over 80% at 100 ug/mL. The study proves that umbelliferone can be a promising skeleton for fungicides discovery. In addition, the primary structure–activity relationship provides a good guidance for the discovery of novel fungicides based on natural products in the future.

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Section: Methodsmentioning

confidence: 99%

Promising Fungicides from Allelochemicals: Synthesis of Umbelliferone Derivatives and Their Structure–Activity Relationships

et al. 2018

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“…The rigid structure of protein was obtained by applying fixed atom constraint. The protein‐binding site was defined, which is derived from carboxin in the SDH structure (PDB code: 2FBW) and prepared for docking process. The structure of compounds K4 , K14 and K20 were drawn using Discovery Studio 2.5 and minimized by applying CHARMM force field.…”

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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“…The mitochondria of Valsa mali Miyabe et Yamada and Rhizoctonia solani were isolated according to previously reported methods (Lv et al, 2017;Zeun, Scalliet, & Oostendorp, 2013).…”

Section: In Vitro Enzyme Assaymentioning

confidence: 99%

“…In the previous research work (Lv et al, 2017), we discovered a novel SDHI lead compound 1 (Figure 1), which exhibited potent activities against H. maydis (EC 50 = 33.5 μM) and R. cerealis (EC 50 = 21.4 μM). At the same time, it also shows an eye-catching activity against H. maydis SDH (IC 50 = 25.4 μM) and R. cerealis SDH (IC 50 = 20.2 μM).…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and antifungal activity of novel cinnamon–pyrazole carboxamide derivatives

Ren

Liu

Jiao

et al. 2018

Drug Development Research

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Hit, Lead & Candidate Discovery To discover succinate dehydrogenase inhibitors with a novel structure, we introduced cinnamic acid structure to optimize the lead structure 1 and synthesized four series of cinnamon–pyrazole carboxamide derivatives. The bioassay data showed that compounds (E)‐N‐(1‐[4‐chlorophenyl]‐4‐cyano‐1H‐pyrazol‐5‐yl)‐3‐(2‐fluorophenyl) acrylamide (5III‐d) and (E)‐3‐(2‐chlorophenyl)‐N‐(1‐[4‐chlorophenyl]‐4‐cyano‐1H‐pyrazol‐5‐yl) acrylamide (5III‐f) showed the significant antifungal activity against three fungi. In addition, 5III‐d and 5III‐f exhibited the excellent inhibitory effect against succinate dehydrogenase (SDH) enzymes with IC50 values ranging from 19.4 to 28.7 μM. The study demonstrates that the chlorine substituent group is present on both the phenyl and pyrazole rings that have a very good effect on the antifungal effect, and the compounds 5III‐d and 5III‐f can act as potential SDH inhibitors (SDHI) and throw a sprat for a new generation of SDHI.

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Design, synthesis and biological evaluation of novel nicotinamide derivatives bearing a substituted pyrazole moiety as potential SDH inhibitors

Abstract: The study suggests that the pyrazole nicotinamide derivative 3 l may serve as a potential SDHI that can be used as a novel antifungal agent, and provides valuable clues for the further design and optimisation of SDH inhibitors. © 2016 Society of Chemical Industry.

Cited by 34 publications

References 28 publications

Promising Fungicides from Allelochemicals: Synthesis of Umbelliferone Derivatives and Their Structure–Activity Relationships

Promising Fungicides from Allelochemicals: Synthesis of Umbelliferone Derivatives and Their Structure–Activity Relationships

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

Design, synthesis, and antifungal activity of novel cinnamon–pyrazole carboxamide derivatives

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