Synthesis, Antifungal Activity, and Molecular Simulation Study of L–Carvone‐Derived 1,3,4‐Oxadiazole‐Thioether Compounds DOI

Rongzhu Wen,

Wengui Duan,

Guishan Lin

et al.

Chemistry & Biodiversity, Journal Year: 2023, Volume and Issue: 20(7)

Published: June 29, 2023

Abstract To discover potent antifungal molecules with new and distinctive structures, 20 novel L‐carvone‐derived 1,3,4‐oxadiazole‐thioether compounds 5 a – t were synthesized through multi‐step reaction of L ‐ carvone, their structures confirmed by FT‐IR, 1 H‐NMR, 13 C‐NMR, HR‐MS. The activities preliminarily tested in vitro method, the results indicated that all title displayed certain against eight plant fungi, especially for P. piricola . Among them, compound i (R= p‐ F) most significant activity deserved further study discovering developing natural product‐based agents. Moreover, two molecular simulation technologies employed investigation structure–activity relationships (SARs). Firstly, reasonable effective 3D‐QSAR model was established comparative field (CoMFA) relationship substituents linked benzene rings inhibitory elucidated. Then, binding mode its potential biological target (CYP51) simulated docking, it found could readily bind CYP51 active site, ligand‐receptor interactions involved three hydrogen bonds several hydrophobic effects.

Language: Английский

Synthesis and Activity of Novel Pyrazole/Pyrrole Carboxamides Containing a Dinitrogen Six-Membered Heterocyclic as Succinate Dehydrogenase and Ergosterol Biosynthesis Inhibitors against Colletotrichum camelliae DOI

Kuai Chen,

Dandan Song,

D. Shi

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 23, 2025

Pyrazole carboxamide derivatives were initially extensively studied as succinate dehydrogenase inhibitors (SDHIs). In the present study, a series of pyrazole/pyrrole carboxamides containing dinitrogen six-membered heterocyclic designed based on our reported active skeletons with dual mode action. Bioactivity results showed that target compound Q18 demonstrated superior antifungal efficacy against Colletotrichum camelliae (C. camelliae) an EC50 value 6.0 mg/L. The in vivo protective activity was 74.7% at 100 Scanning electron microscopy and transmission could disrupt surface morphology mycelia cause lipid peroxidation cell membrane, which further verified by determination relative conductivity malondialdehyde contents. Combined ergosterol content, docking between SDH CYP51, IC50 for (9.7 mg/L), it is concluded potential SDHI biosynthesis inhibitor. Thus, study provides fresh insight into amides.

Language: Английский

Citations

0
Monoterpene amino alcohols in multicomponent synthesis of chiral hetero- and carbocycles DOI
Marina V. Goryaeva,

S.O. Kushch,

Yu.V. Burgart

et al.

Mendeleev Communications, Journal Year: 2025, Volume and Issue: 35(4), P. 464 - 466

Published: Jan. 1, 2025

Language: Английский

Citations

0
Schinus terebinthifolius essential oil and its major component delta-3-carene induce antinociception mediated by serotonergic receptors DOI

Gabriel Carvalho de Souza Santana,

María Jesús,

Anna Beatriz Oliveira Cruz

et al.

Journal of Ethnopharmacology, Journal Year: 2025, Volume and Issue: unknown, P. 120021 - 120021

Published: May 1, 2025

Language: Английский

Citations

0
Synthesis, Antifungal Activity, and Molecular Simulation Study of L–Carvone‐Derived 1,3,4‐Oxadiazole‐Thioether Compounds DOI

Rongzhu Wen,

Wengui Duan,

Guishan Lin

et al.

Chemistry & Biodiversity, Journal Year: 2023, Volume and Issue: 20(7)

Published: June 29, 2023

Abstract To discover potent antifungal molecules with new and distinctive structures, 20 novel L‐carvone‐derived 1,3,4‐oxadiazole‐thioether compounds 5 a – t were synthesized through multi‐step reaction of L ‐ carvone, their structures confirmed by FT‐IR, 1 H‐NMR, 13 C‐NMR, HR‐MS. The activities preliminarily tested in vitro method, the results indicated that all title displayed certain against eight plant fungi, especially for P. piricola . Among them, compound i (R= p‐ F) most significant activity deserved further study discovering developing natural product‐based agents. Moreover, two molecular simulation technologies employed investigation structure–activity relationships (SARs). Firstly, reasonable effective 3D‐QSAR model was established comparative field (CoMFA) relationship substituents linked benzene rings inhibitory elucidated. Then, binding mode its potential biological target (CYP51) simulated docking, it found could readily bind CYP51 active site, ligand‐receptor interactions involved three hydrogen bonds several hydrophobic effects.

Language: Английский

Citations

7