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Synthesis, antifungal activity and mechanism of action of novel chalcone derivatives containing 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole. 2024

Wenliang Zhan, and Ran Zhou, and Piao Mao, and Chunmei Yuan, and Tao Zhang, and Yi Liu, and Jiao Tian, and Hua Wang, and Wei Xue
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering; Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education; Research and Development Center for Fine Chemicals, Guizhou University, Guiyang, 550025, People's Republic of China.

A series of chalcone derivatives containing 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole was designed and synthesized. Structures of all compounds were characterized by 1H NMR, 13C NMR, 19F NMR, and HRMS. The biological activities of the compounds were determined with the mycelial growth rate method, and further studies showed that some compounds had good antifungal activities at the concentration of 100 μg/mL. The EC50 value of compound L31 was 15.9 μg/mL against Phomopsis sp., which were better than that of azoxystrobin (EC50 value was 69.4 μg/mL). In addition, the mechanism of action of compound L31 shown that compound can affect mycelial growth by disrupting membrane integrity against Phomopsis sp., and that the higher the concentration of the compound is, the greater the disruption of membrane integrity is.

UI MeSH Term Description Entries
D008826 Microbial Sensitivity Tests Any tests that demonstrate the relative efficacy of different chemotherapeutic agents against specific microorganisms (i.e., bacteria, fungi, viruses). Bacterial Sensitivity Tests,Drug Sensitivity Assay, Microbial,Minimum Inhibitory Concentration,Antibacterial Susceptibility Breakpoint Determination,Antibiogram,Antimicrobial Susceptibility Breakpoint Determination,Bacterial Sensitivity Test,Breakpoint Determination, Antibacterial Susceptibility,Breakpoint Determination, Antimicrobial Susceptibility,Fungal Drug Sensitivity Tests,Fungus Drug Sensitivity Tests,Sensitivity Test, Bacterial,Sensitivity Tests, Bacterial,Test, Bacterial Sensitivity,Tests, Bacterial Sensitivity,Viral Drug Sensitivity Tests,Virus Drug Sensitivity Tests,Antibiograms,Concentration, Minimum Inhibitory,Concentrations, Minimum Inhibitory,Inhibitory Concentration, Minimum,Inhibitory Concentrations, Minimum,Microbial Sensitivity Test,Minimum Inhibitory Concentrations,Sensitivity Test, Microbial,Sensitivity Tests, Microbial,Test, Microbial Sensitivity,Tests, Microbial Sensitivity
D002599 Chalcone An aromatic KETONE that forms the core molecule of CHALCONES. Benzalacetophenone,Benzylideneacetophenone,1,3-Diphenyl-2-Propen-1-One,Chalkone,1,3 Diphenyl 2 Propen 1 One
D000935 Antifungal Agents Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. Anti-Fungal Agents,Antifungal Agent,Fungicides, Therapeutic,Antibiotics, Antifungal,Therapeutic Fungicides,Agent, Antifungal,Anti Fungal Agents,Antifungal Antibiotics
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013830 Thiadiazoles Heterocyclic compounds composed of a five-membered heterocyclic ring which contains one sulfur and two nitrogen atoms. Thiadiazole
D014230 Triazoles Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3. Triazole
D047188 Chalcones Derivatives of CHALCONE that are important intermediates in the formation of FLAVONOIDS with anti-fungal, anti-bacterial, anti-inflammatory, and anti-tumor properties. 1,3-Diphenyl-propanediones,1,3-Diphenyl-propenones,1,3-Diphenylpropanediones,1,3-Diphenylpropenones,Chalconoids,1,3 Diphenyl propanediones,1,3 Diphenyl propenones,1,3 Diphenylpropanediones,1,3 Diphenylpropenones
D025282 Mycelium The body of a fungus which is made up of HYPHAE. Myceliums

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