Browse
Submit Data
Databases
API
Help

Dataset Information

5 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

New Insecticidal Agents from Halogenation/Acylation of the Furyl-Ring of Fraxinellone.

ABSTRACT: Introduction of the halogen atom or the acyl group at the C-ring of fraxinellone was investigated. Some unexpected halogenation products were obtained with the different chlorination/bromination reagents, and their possible reaction mechanisms were also proposed. Seven key steric structures of 2a', 2b, 2b', 2c', 3a, 3b, and one isomer (5'?-Cl) of 2a were further confirmed by single-crystal X-ray diffraction. Especially compounds 2a, 2a', 3a and 3c exhibited more potent insecticidal activity than toosendanin. Some structure-activity relationships of tested compounds were also described.

SUBMITTER: Guo Y

PROVIDER: S-EPMC5075773 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

New Insecticidal Agents from Halogenation/Acylation of the Furyl-Ring of Fraxinellone.

Guo Yong Y Yang Ruige R Xu Hui H

Scientific reports 20161024

Introduction of the halogen atom or the acyl group at the C-ring of fraxinellone was investigated. Some unexpected halogenation products were obtained with the different chlorination/bromination reagents, and their possible reaction mechanisms were also proposed. Seven key steric structures of 2a', 2b, 2b', 2c', 3a, 3b, and one isomer (5'α-Cl) of 2a were further confirmed by single-crystal X-ray diffraction. Especially compounds 2a, 2a', 3a and 3c exhibited more potent insecticidal activity than ...[more]

PMID: 27775033

Similar Datasets

Furan-Site Bromination and Transformations of Fraxinellone as Insecticidal Agents Against Mythimna separata Walker.

Project description:Furan ring of limoninoids is critical in exhibiting insecticidal activity. Herein, fraxinellone (1) was used as a template of furan-containing natural products and a series of its derivatives was synthesized by selective bromination in good yields on gram-scale and following Suzuki-Miyaura or Sonogashira coupling reactions in moderate to good yields. Bromination of limonin (9) was also accomplished without altering other functional groups in high yield. Furthermore, an evaluation of insecticidal activity against the instar larvae of Mythimna separata showed that derivatives 2, 3b, 3g, 5a, 5d and 5h displayed more potent insecticidal activity than 1 and toosendanin.

| S-EPMC5976728 | biostudies-literature

Semi-Synthesis of C-Ring Cyclopropyl Analogues of Fraxinellone and Their Insecticidal Activity Against Mythimna separata Walker.

Project description:Fraxinellone (1) is a naturally occurring degraded limonoid isolated from Meliaceae and Rutaceae plants. As a potential natural-product-based insecticidal agent, fraxinellone has been structurally modified to improve its activity. Furan ring of fraxinellone is critical in exhibiting its insecticidal activity, but with few modifications. Herein, C-ring-modified cyclopropyl analogues were semi-synthesized by Rh(II)-catalyzed cyclopropanation. The structures of the target compounds were well characterized by NMR and HRMS. The precise three-dimensional structural information of 3a was established by X-ray crystallography. Their insecticidal activity was evaluated against Mythimna separata Walker by a leaf-dipping method. Compound 3c exhibited stronger insecticidal activity than 1 and toosendanin against M. separata with teratogenic symptoms during the different periods, implying that cyclopropanation of the furan ring could strengthen the insecticidal activity of fraxinellone.

| S-EPMC7179169 | biostudies-literature

Semisynthesis and insecticidal activity of some novel fraxinellone-based thioethers containing 1,3,4-oxadiazole moiety.

Project description:Two series of novel fraxinellone-based thioethers containing 1,3,4-oxadiazole moiety were prepared as insecticidal agents against the oriental armyworm, Mythimna separata Walker. The structural assignment was based on the spectroscopic and X-ray analysis data. Among all the target compounds, compounds 4b, 4k, 5b, 5j and 5k exhibited more potent insecticidal activity with final mortality rates (FMRs) of more than 65%, especially 4k with the FMR of 75.9%, when compared with toosendanin. Some interesting results of structure-activity relationships are also discussed.

| S-EPMC5750010 | biostudies-literature

Fraxinellone.

Project description:In the title compound, C(14)H(16)O(3) [systematic name: (3R*,3aR*)-3-(3-furan-yl)-3a,7-dimethyl-3a,4,5,6-tetra-hydro-2-benzofuran-1(3H)-one], the pendant methyl and furan groups attached to the stereogenic centres lie to the same side of the fused ring system. The dihedral angle between the five-membered rings is 74.8?(2)°; the fused five-membered ring adopts a twisted conformation. In the crystal, mol-ecules are linked by weak C-H?O inter-actions, which generate [100] chains.

| S-EPMC3120588 | biostudies-literature

Antitumor agents. 284. New desmosdumotin B analogues with bicyclic B-ring as cytotoxic and antitubulin agents.

Project description:We previously reported that the biological activity of analogues of desmosdumotin B (1) was dramatically changed depending on the B-ring system. A naphthalene B-ring analogue 3 exerted potent in vitro activity against a diverse panel of human tumor cell lines with GI(50) values of 0.8-2.1 ?M. In contrast, 1 analogues with a phenyl B-ring showed unique selective activity against P-glycoprotein (P-gp) overexpressing multidrug resistant cell line. We have now prepared and evaluated 1 analogues with bicyclic or tricyclic aromatic B-ring systems as in vitro inhibitors of human cancer cell line proliferation. Among all synthesized derivatives, 21 with a benzo[b]thiophenyl B-ring was highly active, with GI(50) values of 0.06-0.16 ?M, and this activity was not influenced by overexpression of P-gp. Furthermore, 21 inhibited tubulin assembly in vitro with an IC(50) value of 2.0 ?M and colchicine binding by 78% as well as cellular microtubule polymerization and spindle formation.

| S-EPMC3048907 | biostudies-literature

The action of chloride peroxidase on 4-chloroaniline. N-oxidation and ring halogenation.

Project description:Chloride peroxidase catalyses both the ring halogenation and N-oxidation reactions of 4-chloroaniline by H2O2 and either KCl or KBr. In the absence of any halide salt only the N-oxidation reaction was observed, with the resulting conversion of 4-chloroaniline into 4-chloronitrosobenzene. The N-oxidation reaction proceeded even more rapidly in the presence of Cl- or Br-, in spite of the fact that ring halogenation was also a rapid reaction. The enhancement of N-oxidation was highly dependent on the pH of the media and displayed an optimum in the region of pH 3.5-4.0. No rate enhancement was observed above pH 5.5. KF partially inhibited the rate of N-oxidation in a pH-dependent manner. On the basis of calculated catalytic-centre activity the N-oxidation reaction was the major reaction at pH 3.5 or higher, whereas the ring-halogenation reaction became the major reaction below pH 3.5. In the presence of high concentrations of 4-chloroaniline relative to H2O2 the reaction intermediate, 4-chlorophenylhydroxylamine, was detected for the first time in a chloride peroxidase-catalysed reaction with this arylamine substrate. These findings were interpreted on the basis of current knowledge concerning the mechanism of action of chloride peroxidase.

| S-EPMC1162477 | biostudies-other

Furan-site transformations of obacunone as potent insecticidal agents.

Project description:Furan ring is a key pharmacophore for insecticidal activity of limoninoids. To develop natural-product-based insecticidal agents, a series of furan-site transformations (2, 3 and 3a–j) of obacunone were synthesized by selective bromination and following coupling reactions without altering other functional groups. Bioassays indicated that derivatives 3e, 3f and 3j displayed more potent insecticidal activity than obacunone and toosendanin against the instar larvae of Mythimna separate Walker. Besides, their structure–activity relationships were discussed.

| S-EPMC6298901 | biostudies-other

Chemical design and bioefficacy screening of new insect growth regulators as potential insecticidal agents against Spodoptera littoralis (Boisd.).

Project description:The 13 new compounds were chemically synthesized and their spectroscopic analysis was done to determine their chemical structure. All the compounds were screened for their insecticidal potential against Spodoptera littoralis (Boisd.). Among the tested compounds, the compound 13 was found to be the most potent. It displayed one fold more activity than a reported insect growth regulator, fenoxycarb. The other target compounds demonstrated weak to strong toxicological activities against Spodoptera littoralis (Boisd.).

| S-EPMC6881669 | biostudies-literature

New antimicrobial agents development

Project description:With the growing antibiotic resistance of Staphylococcus aureus, it is urgent to discover new antimicrobials to solve this problem. By bacterial growth based high-throughput screening, we identified two compounds, C218-0546 and STK848198, with effective antimicrobial activity against S. aureus. This study aims to explore the model of action of the compounds by transcriptomic analysis and other microbiological methods. The transcriptomic data would provide us information about the regulated genes, and hence help us further study the underlying antimicrobial mechanisms by the compounds.

2024-05-20 | PXD052423 | iProX

Antitumor agents. 274. A new synthetic strategy for E-ring SAR study of antofine and cryptopleurine analogues.

Project description:A new versatile synthetic methodology for the synthesis of enantiomerically pure natural phenanthroindolizidines and phenanthroquinolizidines has been established and described. Natural products R-antofine and R-cryptopleurine, as well as a novel E-ring expanded analogue 13c (E7), 12-oxo-S-antofine (17), and 12N-methyl-12-aza-S-antofine (18) were synthesized with the new method. This strategy will greatly facilitate future SAR studies on the natural alkaloids with E-ring variations.

| S-EPMC2849728 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

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