Quantitative structure-activity studies of insect growth regulators xiv. Three-dimensional quantitative structure-activity relationship of ecdysone agonists including dibenzoylhydrazine analogs

Nakagawa, Yoshiaki; Hattori, Kazunari; Shimizu, Bun-ichi; Akamatsu, Miki; Miyagawa, Hisashi; Ueno, Tamio

doi:10.1002/(sici)1096-9063(199808)53:4<267::aid-ps765>3.0.co;2-u

Cited by 47 publications

(15 citation statements)

References 28 publications

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“…Xuhong13 reported molecular modelling studies on the similarity between the three‐dimensional structures of the BTBH analogues and 20E. Nakagawa et al 14 proposed another similarity model between the BTBH analogues and 20E using the 3D‐QSAR procedure. More research will be needed in order to clarify the structural similarity between 20E and the BTBH insecticides, including our analogues.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and insecticidal activity of benzoheterocyclic analogues of N′‐benzoyl‐N‐(tert‐butyl)benzohydrazide: Part 1. Design of benzoheterocyclic analogues

Sawada¹,

Yanai²,

Nakagawa³

et al. 2002

Pest Management Science

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The N'-benzoyl group of N-tert-butyl-N'-benzoyl-3,5-dimethylbenzohydrazide (1) was converted to a series of benzoheterocyclecarbonyl groups in order to investigate the potential usefulness of superimposing a hydrazine insecticide on 20-hydroxyecdysone. A series of analogues with benzodioxole, benzodioxane, benzodioxapine, indole, benzoxazole, benzoxazine or benzothiazole instead of the phenyl group of (1) were synthesized and tested for their insecticidal activity against the common cutworm (Spodoptera litura F). N-tert-Butyl-N'-(3,5-dimethylbenzoyl)-1,3-benzodioxole-5-carbohydrazide and N-tert-butyl-N'-(3,5-dimethylbenzoyl)-2,3-dihydro-1,4-benzodioxine-6-carbohydrazide showed high insecticidal activities, superior to that of (1) and equal to that of the commercial insecticide tebufenozide (RH-5992).

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Section: Resultsmentioning

confidence: 99%

Synthesis and insecticidal activity of benzoheterocyclic analogues of N′‐benzoyl‐N‐(tert‐butyl)benzohydrazide: Part 1. Design of benzoheterocyclic analogues

Sawada¹,

Yanai²,

Nakagawa³

et al. 2002

Pest Management Science

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“…Nakagawa et al reported a series of substituted DBHs and analyzed the relationship between the substituent properties and the inhibitory activity by QSAR methods, which revealed the strong influence of the hydrophobicity of the DBH on molting activity [15][16][17][18][19]. Holmwood et al designed imidazole-and thiadiazoloimidazole-type ecdysone agonists based on the shapes of the DBH-binding pockets [20].…”

Section: Introductionmentioning

confidence: 99%

Exploration of the binding affinities between ecdysone agonists and EcR/USP by docking and MM-PB/GBSA approaches

Xie

et al. 2017

J Mol Model

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Ecdysone receptor (EcR) is a significant target in the identification of new environmentally friendly pesticides. There are two types of ecdysone agonists: steroidal ecdysone agonists and dibenzoylhydrazines (DBHs). In this study, various modeling methods (homology modeling, molecular docking, MD simulation, binding free energy calculation, and per-residue binding free energy decomposition) were utilized to study the different binding mechanisms of two types of ecdysone agonists. Our theoretical results indicated that the relative binding potencies of DBHs can be ranked sufficiently accurately using the MOE docking method. However, MM/PBSA calculations more accurately predicted the binding affinities between steroidal ecdysone agonists and EcR-LBD. To identify the key residues involved in ecdysone agonist binding, the binding free energy (ΔG ) was decomposed into the energy contributions of individual residues. The results revealed that nine residues-Ile339, Thr343, Met380, Met381, Tyr403, Tyr408, Asp419, Gln503, and Asn504-determined the binding affinities of the DBHs. Glu309, Met342, Arg383, Arg387, and Leu396 were important influences on the binding affinities of the steroidal ecdysone agonists. Graphical abstract The ecdysone receptor (EcR) is related to insect growth and has been shown to be a useful target for insecticides.

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“…Since the first nonsteroidal ecdysone agonist, RH5849, and its larvicidal activity were reported [3,4], extensive explorations of its derivatives, dibenzoyl-hydrazines, have been conducted [5][6][7][8]. Nakagawa et al [9][10][11][12][13][14] reported the 3D-QSAR and QSAR studies of dibenzoyl-hydrazine analogs using the CoMFA procedure and the semiempirical parameters, respectively. The results indicated that hydrophobic, steric, and electrostatic effects were likely to participate in modifying the larvicidal activity.…”

Section: Introductionmentioning

confidence: 99%

QSAR and 3D-QSAR studies of the diacyl-hydrazine derivatives containing furan rings based on the density functional theory

et al. 2010

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QSAR studies of 27 diacyl-hydrazine derivatives containing furan rings were conducted and compared with the DFT method and AM1-MOPAC method. q 2 values of 0.61 and 0.40 validated the predictability and reliability of eq. (5) from the DFT method were higher than those of eq. (6) from the AM1-MOPAC method. The DFT-optimized conformations and ESP-fitting charges of the target compounds were also used for 3D-QSAR analysis, including CoMFA and CoMSIA. The leave-one-out cross-validation correlation coefficient and the good correlation between the predicted and experimental activities of excluded test compounds revealed that CoMFA and CoMSIA models were robust. The QSAR results were consistent with the 3D-QSAR results, indicating that the electrostatic and hydrophobic properties of the target compounds were significant to the biological activity. These models are useful tools for predicting the larvicidal activities of new compounds and designing new specific insect growth regulators. diacyl-hydrazine, QSAR, 3D-QSAR, DFT, insect growth regulator

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Quantitative structure-activity studies of insect growth regulators xiv. Three-dimensional quantitative structure-activity relationship of ecdysone agonists including dibenzoylhydrazine analogs

Cited by 47 publications

References 28 publications

Synthesis and insecticidal activity of benzoheterocyclic analogues of N′‐benzoyl‐N‐(tert‐butyl)benzohydrazide: Part 1. Design of benzoheterocyclic analogues

Synthesis and insecticidal activity of benzoheterocyclic analogues of N′‐benzoyl‐N‐(tert‐butyl)benzohydrazide: Part 1. Design of benzoheterocyclic analogues

Exploration of the binding affinities between ecdysone agonists and EcR/USP by docking and MM-PB/GBSA approaches

QSAR and 3D-QSAR studies of the diacyl-hydrazine derivatives containing furan rings based on the density functional theory

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