Novel 5-(Trifluoromethyl)-1,2,4-oxadiazole-Based Pyrimidin-4-ether Histone Deacetylase Inhibitors for Controlling Rust Disease: Design, Synthesis, Activity, and Structure–Activity Relationship

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

Published: Feb. 12, 2025

Rust disease, an important plant pathogen, can lead to reduced crop or fruit production. Trifluoromethyloxadiazole (TFMO) is a class of histone deacetylase inhibitors (HDACs). Herein, series 5-(trifluoromethyl)-1,2,4-oxadiazole (TFMO)-based pyrimidin-4-ether derivatives were designed and synthesized. Antirust bioassay results TFMOs showed that some them possessed excellent activities against rust pathogens, such as Puccinia sorghi, Phakopsora pachyrhizi, rubigo. The most active compound, 3-(5-(((6-(difluoromethyl)pyrimidin-4-yl)oxy)methyl)thiophen-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole (XII6), exhibited 50% control P. pachyrhizi at 0.780 mg/L, which was significantly better than the commercial fungicide azoxystrobin (0%) same concentration. field trial indicated compound effect rubigo 116 g a.i./ha. acute toxic XII6 has low toxicity. Furthermore, enzyme activity strong, nonselective HDAC inhibitor. Finally, structure–activity relationship established, XII6-HDAC binding mode carried out based on crystal structure hHDAC1, hHDAC4, hHDAC6. This work provided for further optimization.

Language: Английский

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A review on pyrimidine‐based derivatives: Synthesis and their biological application

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: 61(7), P. 1159 - 1179

Published: May 21, 2024

Abstract Pyrimidine‐based derivatives have attracted a lot of interest in heterocyclic chemistry due to its versatile structure and diverse biological activities. This study provides comprehensive overview synthetic strategy different pyrimidine ring highlights their importance. In this article, we start off by going through the fundamental procedures for synthesis scaffolds, including both conventional contemporary techniques. These works cover range therapeutic domains, such as effects that are anticancer, antibacterial, antiviral, anti‐inflammatory, antioxidant, antimalarial, so on. Moreover, summarized with discussion future prospects challenges field chemistry. thorough review is significant resource researchers medicinal related fields since it offers insightful information about methods applications pyrimidine‐based derivatives.

Language: Английский

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Synthesis, Antifungal, and Antibacterial Activities of Novel Benzoylurea Derivatives Containing a Pyrimidine Moiety

Molecules, Journal Year: 2023, Volume and Issue: 28(18), P. 6498 - 6498

Published: Sept. 7, 2023

To explore more efficient and less toxic antibacterial antifungal pesticides, we utilized 2,6-difluorobenzamide as a starting material ultimately synthesized 23 novel benzoylurea derivatives containing pyrimidine moiety. Their structures were characterized confirmed by 1H NMR, 13C 19F HRMS. The bioassay results demonstrated that some of the title compounds exhibited moderate to good in vitro activities against Botrytis cinerea cucumber, tobacco, blueberry, Phomopsis sp., Rhizoctonia solani. Notably, 4j 4l displayed EC50 values 6.72 5.21 μg/mL solani, respectively, which comparable hymexazol (6.11 μg/mL). Meanwhile, at 200 100 concentrations, target 4a-4w lower Xanthomonas oryzae pv. oryzicola citri subsp. citri, compared those thiodiazole copper. Furthermore, molecular docking simulation compound formed hydrogen bonds with SER-17 SER-39 succinate dehydrogenase (SDH), providing possible explanation for mechanism action between SDH. This study represents first report on

Language: Английский

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Synthesis of Fused Pyrimidines from Azole Amines and Their Biological Activity

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(43)

Published: Aug. 3, 2024

Abstract Fused pyrimidines are a class of heterocyclic compounds that have gained considerable interest due to their extensive biological activities and potential applications in drug development. This review article aims provide comprehensive overview the latest synthetic approaches fused pyrimidines, including Michael reactions, multicomponent metal‐catalyzed photocatalytic peroxide‐mediated inverse electron demand Diels–Alder reactions. Furthermore, these compounds, such as ability combat cancer microbial infections, also discussed. summarizes existing literature on synthesis activity from 2020 2023. We hope this will inspire development more effective less toxic pyrimidine drugs with well‐designed structures.

Language: Английский

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Advancements in the Synthesis of Triazolopyrimidines

Current Organic Chemistry, Journal Year: 2024, Volume and Issue: 28(20), P. 1567 - 1578

Published: June 26, 2024

: The triazolopyrimidine scaffold indeed holds a prominent place in medicinal chemistry due to its versatile pharmacological properties. Researchers have explored the and derivatives for various therapeutic applications. unique structure of has made it valuable template designing medicinally active molecules. literature is full studies showcasing synthesis biological activities compounds containing ring, either fused or coupled with other heterocycles. aim this review provide comprehensive general summary recent advancements (Year 2021 present).

Language: Английский

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Five-membered ring systems: With more than 1 N atom

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 211 - 257

Published: Jan. 1, 2024

Language: Английский

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