Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis and insecticidal activities of 5-deoxyavermectin B2a oxime ester derivatives.

ABSTRACT: Three series of avermectin B2a oxime ester derivatives were synthesized using avermectin B2a as starting material. All of the compounds were characterized by ¹H NMR, ¹³C NMR, and HRMS. Bioassay results indicated that some of the derivatives (8b, 8c, 8d, 8f, 11k, 11l, 14c, 14j) showed potent insecticidal activities against Myzus persicae, Caenorhabditis elegans, or Tetranychus cinnabarinus. As shown by initial insecticidal activity data, compound 8d showed excellent activities (>90%) against M. persicae and C. elegans, which were more potent than that of avermectin B2a. Compound 8d might be a lead compound for designing new avermectin B2a derivatives.

SUBMITTER: Sun G

PROVIDER: S-EPMC9078043 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis and insecticidal activities of 5-deoxyavermectin B2a oxime ester derivatives.

Sun Guoshao G Zhang Jingjing J Jin Shuhui S Zhang Jianjun J

RSC advances 20180122 7

Three series of avermectin B2a oxime ester derivatives were synthesized using avermectin B2a as starting material. All of the compounds were characterized by 1H NMR, 13C NMR, and HRMS. Bioassay results indicated that some of the derivatives (8b, 8c, 8d, 8f, 11k, 11l, 14c, 14j) showed potent insecticidal activities against Myzus persicae, Caenorhabditis elegans, or Tetranychus cinnabarinus. As shown by initial insecticidal activity data, compound 8d show ...[more]

PMID: 35542930

Similar Datasets

Ovicidal and Insecticidal Activities of Pyriproxyfen Derivatives with an Oxime Ester Group.

Project description:Based on the structural framework of a pyriproxyfen metabolite, nineteen oxime ester derivatives were synthesized via reaction of the carboxylic acids with 4-(2-(2-pyridinyloxy)ethoxy)benzaldehyde oxime. The corresponding structures were comprehensively characterized by ¹H-nuclear magnetic resonance (NMR), 13C-NMR, and electrospray ionization high-resolution mass spectrometry (ESI-HRMS). All of the compounds were screened for their insecticidal activities against Plutella xylostella and Myzus persicae, and for their ovicidal activities against Helicoverpa armigera eggs. The results obtained show that most of the oxime ester derivatives displayed moderate to high insecticidal activities and ovicidal activities at a concentration of 600 ug/mL. In particular, the ovicidal activity of compounds 5j, 5o, 5p, 5q, and 5s was determined to be 100%. Importantly, some of the compounds presented even higher biological activities than the reference compound pyriproxyfen. For example, compound 5j displayed an insecticidal activity value of 87.5% against Myzus persicae, whereas the activity value of pyriproxyfen was 68.3% at a concentration of 600 ug/mL. Among the synthesized compounds 5j and 5s exhibited broad biological activity spectra.

| S-EPMC6152621 | biostudies-literature

New pentadienone oxime ester derivatives: synthesis and anti-inflammatory activity.

Project description:To develop novel anti-inflammatory agents, a series of new pentadienone oxime ester compounds were designed and synthesized. The structures were determined by IR, 1H NMR, 13 C NMR, and HRMS. All compounds have been screened for their anti-inflammatory activity by evaluating their inhibition against LPS-induced nitric oxide (NO) release in RAW 264.7 cell. Among them, compound 5j was found to be one of the most potent compounds in inhibiting NO and IL-6 (IC50 values were 6.66 µM and 5.07 µM, respectively). Preliminary mechanism studies show that title compound 5j could significantly suppress expressions of nitric oxide synthase, COX-2, and NO, IL-6 through Toll-like receptor 4/mitogen-activated protein kinases/NF-κB signalling pathway. These data support further studies to assess rational design of more efficient pentadienone oxime ester derivatives with anti-inflammatory activity in the future.

| S-EPMC6010105 | biostudies-literature

Synthesis of Halopyrazole Matrine Derivatives and Their Insecticidal and Fungicidal Activities.

Project description:Matrine is a traditional botanical pesticide with a broad-spectrum biological activity that is widely applied in agriculture. Halopyrazole groups are successfully introduced to the C13 of matrine to synthesize eight new derivatives with a yield of 78-87%. The insecticidal activity results show that the introduction of halopyrazole groups can significantly improve the insecticidal activity of matrine on Plutella xylostella, Mythimna separata and Spodoptera frugiperda with a corrected mortality rate of 100%, which is 25-65% higher than matrine. The fungicidal activity results indicate that derivatives have a high inhibitory effect on Ceratobasidium cornigerum, Cibberella sanbinetti, Gibberrlla zeae and Collectot tichum gloeosporioides. Thereinto, 4-Cl-Pyr-Mat has the best result, with an inhibition rate of 23-33% higher than that of matrine. Therefore, the introduction of halogenated pyrazole groups can improve the agricultural activity of matrine.

| S-EPMC9370413 | biostudies-literature

Synthesis and Insecticidal/Fungicidal Activities of Triazone Derivatives Containing Acylhydrazone Moieties.

Project description:A series of novel triazone derivatives containing aldehyde hydrazone or ketone hydrazone moieties were designed, synthesized and their biological activities were investigated against Aphis craccivora, Culex pipiens pallens, Helicoverpa armigera, Ostrinia nubilalis, Mythimna separata and 14 Kinds of fungi. Most of the aldehyde hydrazone exhibited excellent insecticidal activities against A. craccivora. In particular, the aphicidal activities of compounds 3t (35%) and 3w (30%) were equivalent to pymetrozine (30%) at 5 mg/kg. The aphicidal activities of derivatives 3p, 3u, 3y, 5g, 5i, 5l, 5q and 5u against C. pipiens pallens were higher than that of pymetrozine. Compound 3u (100%) exhibited good larvicidal activities against C. pipiens pallens at 0.25 mg/kg. Most derivatives exhibited broad-spectrum fungicidal activities against 14 kinds of plant fungi at 50 mg/kg. Thirty-nine compounds exhibited a more than 50% inhibition rate against Physalospora piricola. Compounds 3h, 3t and 3w were expected to be the leading structure for the development of new triazone insecticides agents.

| S-EPMC11767570 | biostudies-literature

Synthesis, Insecticidal Activities and Mode of Action of Novel Imidazopyridine Mesoionic Derivatives Containing an Amido group

Project description:KEGG enrichment analysis showed that the proteins which differentially expressed between the control and C6-treated groups are mainly enriched in pathways of neurodegeneration (ko05022), amyotrophic lateral sclerosis (ko05014), prion disease (ko05020), parkinson disease (ko05012) and huntington disease (ko05016). These pathways are all related to the nervous system, and associated with mitochondrial dysfunction, oxidative stress, and axonal dysfunction. The above results suggested that compound C6 may have effects on the nervous system of A. craccivora.

2022-06-27 | PXD034928 |

Synthesis and bioactivities evaluation of oleanolic acid oxime ester derivatives as α-glucosidase and α-amylase inhibitors.

Project description:Different oleanolic acid (OA) oxime ester derivatives (3a-3t) were designed and synthesised to develop inhibitors against α-glucosidase and α-amylase. All the synthesised OA derivatives were evaluated against α-glucosidase and α-amylase in vitro. Among them, compound 3a showed the highest α-glucosidase inhibition with an IC50 of 0.35 µM, which was ∼1900 times stronger than that of acarbose, meanwhile compound 3f exhibited the highest α-amylase inhibitory with an IC50 of 3.80 µM that was ∼26 times higher than that of acarbose. The inhibition kinetic studies showed that the inhibitory mechanism of compounds 3a and 3f were reversible and mixed types towards α-glucosidase and α-amylase, respectively. Molecular docking studies analysed the interaction between compound and two enzymes, respectively. Furthermore, cytotoxicity evaluation assay demonstrated a high level of safety profile of compounds 3a and 3f against 3T3-L1 and HepG2 cells.HighlightsOleanolic acid oxime ester derivatives (3a-3t) were synthesised and screened against α-glucosidase and α-amylase.Compound 3a showed the highest α-glucosidase inhibitory with IC50 of 0.35 µM.Compound 3f presented the highest α-amylase inhibitory with IC50 of 3.80 µM.Kinetic studies and in silico studies analysed the binding between compounds and α-glucosidase or α-amylase.

| S-EPMC8757604 | biostudies-literature

Investigation of Novel Pesticides with Insecticidal and Antifungal Activities: Design, Synthesis and SAR Studies of Benzoylpyrimidinylurea Derivatives.

Project description:In order to find pesticides with insecticidal and antifungal activities, a series of novel benzoyl pyrimidinylurea derivatives were designed and synthesized. All target compounds were identified by ¹H-NMR spectroscopy and HRMS. Insecticidal and antifungal activity of these compounds were evaluated and the structure-activity relationships (SAR) were clearly and comprehensively illustrated. Compound 7, with low toxicity to zebrafish (LC50 = 378.387 µg mL-1) showed 100% inhibition against mosquito (Culex pipiens pallens) at 0.25 µg mL-1. Both compounds 19 and 25 exhibited broad-spectrum fungicidal activity (>50% inhibitory activities against 13 phytopathogenic fungi), which were better than those of the commercial pesticide pyrimethanil (>50% inhibitory activities against eight phytopathogenic fungi). Furthermore, compounds 19 and 25 exhibited protective activity against Sclerotinia sclerotiorum on leaves of Brassica oleracea L. during in vivo experiments.

| S-EPMC6225173 | biostudies-literature

An efficient synthesis of pyridoxal oxime derivatives under microwave irradiation.

Project description:Quaternary salts of pyridoxal oxime have been synthesized by the quaternization of pyridoxal oxime with substituted phenacyl bromides using microwave heating. Microwave-assisted rapid synthesis was done both in solvent (acetone) and under solvent-free conditions. Good to excellent yields (58%-94%) were obtained in acetone in very short reaction times (3-5 min) as well as in the solvent-free procedure (42%-78%) in very short reaction times (7-10 min) too. Effective metodologies for the preparation of pyridoxal oxime quaternary salts, having the advantagies of being eco-friendly, easy to handle, and performed in shorter reactions time are presented. The structure of compound 7, in which a 4-fluorophenacyl moiety is bonded to the pyridinium ring nitrogen atom, was unequivocally confirmed by the single-crystal X-ray diffraction method.

| S-EPMC6271574 | biostudies-literature

New Estrone Oxime Derivatives: Synthesis, Cytotoxic Evaluation and Docking Studies.

Project description:The interest in the introduction of the oxime group in molecules aiming to improve their biological effects is increasing. This work aimed to develop new steroidal oximes of the estrane series with potential antitumor interest. For this, several oximes were synthesized by reaction of hydroxylamine with the 17-ketone of estrone derivatives. Then, their cytotoxicity was evaluated in six cell lines. An estrogenicity assay, a cell cycle distribution analysis and a fluorescence microscopy study with Hoechst 3358 staining were performed with the most promising compound. In addition, molecular docking studies against estrogen receptor α, steroid sulfatase, 17β-hydroxysteroid dehydrogenase type 1 and β-tubulin were also accomplished. The 2-nitroestrone oxime showed higher cytotoxicity than the parent compound on MCF-7 cancer cells. Furthermore, the oximes bearing halogen groups in A-ring evidenced selectivity for HepaRG cells. Remarkably, the Δ9,11-estrone oxime was the most cytotoxic and arrested LNCaP cells in the G2/M phase. Fluorescence microscopy studies showed the presence of condensed DNA typical of prophase and condensed and fragmented nuclei characteristic of apoptosis. However, this oxime promoted the proliferation of T47-D cells. Interestingly, molecular docking studies estimated a strong interaction between Δ9,11-estrone oxime and estrogen receptor α and β-tubulin, which may account for the described effects.

| S-EPMC8125528 | biostudies-literature

Design, synthesis and insecticidal activity of novel phenylurea derivatives.

Project description:A series of novel phenylurea derivatives were designed and synthesized according to the method of active groups linkage and the principle of aromatic groups bioisosterism in this study. The structures of the novel phenylurea derivatives were confirmed based on ESI-MS, IR and 1H-NMR spectral data. All of the compounds were evaluated for the insecticidal activity against the third instars larvae of Spodoptera exigua Hiibner, Plutella xyllostella Linnaeus, Helicoverpa armigera Hubner and Pieris rapae Linne respectively, at the concentration of 10 mg/L. The results showed that all of the derivatives displayed strong insecticidal activity. Most of the compounds presented higher insecticidal activity against S. exigua than the reference compounds tebufenozide, chlorbenzuron and metaflumizone. Among the synthesized compounds, 3b, 3d, 3f, 4b and 4g displayed broad spectrum insecticidal activity.

| S-EPMC6272132 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data