Synthesis of racemic germicidin

Lokot, I. P.; Pashkovsky, Felix S.; Лахвич, Ф. А.

doi:10.1070/mc1999v009n01abeh001006

Cited by 3 publications

(4 citation statements)

References 17 publications

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“…The possible mechanistic model suggests that the intermediate enolacylate formed from direct 4-OH acylation of 4-hydroxy-6-methyl-2-pyrone can be isomerized in situ under the action of DMAP or BF 3 •OEt 2 to render the 3-acyl product. 21 The insignificant difference in the yield of Po between both procedures revealed their comparable efficiency. Therefore, we chose the more convenient one-pot procedure A for the synthesis of the target Po analogues 2−32 using various organic acids (Scheme 2).…”

Section: Resultsmentioning

confidence: 97%

“…Two different reported procedures were employed to prepare Po from commercially available 4-methylvaleric acid and compound 1 on a decagram scale (Scheme ), serving as a reference for the subsequent syntheses. The possible mechanistic model suggests that the intermediate enolacylate formed from direct 4-OH acylation of 4-hydroxy-6-methyl-2-pyrone can be isomerized in situ under the action of DMAP or BF 3 •OEt 2 to render the 3-acyl product . The insignificant difference in the yield of Po between both procedures revealed their comparable efficiency.…”

Section: Results and Discussionmentioning

confidence: 97%

“…13 To elucidate the influence of alkyl groups on this activity, Topomer CoMFA is used to build the QSAR between the molecular field information and the alkyl substituents. As shown in Table S4, the resulting Topomer CoMFA model had q cv 2 of 0.679 (>0.5), r ncv 2 of 0.874 (>0.6), SEE ncv of 0.22, and F-value of 72.582 [>5.780 of F 0.01 (2,21)], providing the statistically significant ability to predict the activity. The experimental and predicted pEC 50 values of the Po analogues in training and test sets possess a significant linear correlation, as shown in Table S5 and Figure As illustrated in the steric contour maps (Figure 2), the green and red contour maps are overlaid near and far from the scaffold, respectively, suggesting that optimal alkyl substituents are characterized by shorter chain lengths (number of C atoms <8) or smaller sizes.…”

Section: D-qsar By Topomermentioning

confidence: 99%

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Chelation of the Optimal Antifungal Pogostone Analogue with Copper(II) to Explore the Dual Antifungal and Antibacterial Agent

Wang,

Yuan,

et al. 2024

J. Agric. Food Chem.

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In an ongoing effort to explore more potent antifungal pogostone (Po) analogues, we maintained the previously identified 3-acetyl-4-hydroxy-2-pyrone core motif while synthesizing a series of Po analogues with variations in the alkyl side chain. The in vitro bioassay results revealed that compound 21 was the most potent antifungal analogue with an EC 50 value of 1.1 μg/mL against Sclerotinia sclerotiorum (Lib.) de Bary. Meanwhile, its Cu(II) complex 34 manifested significantly enhanced antibacterial activity against Xanthomonas campestris pv campestris (Xcc) with a minimum inhibitory concentration (MIC) value of 300 μg/mL compared with 21 (MIC = 700 μg/mL). Complex 34 exhibited a striking preventive effect against S. sclerotiorum and Xcc in rape leaves, with control efficacies of 98.8% (50 μg/mL) and 80.7% (1000 μg/mL), respectively. The 3D-QSAR models generated using Topomer comparative molecular field analysis indicated that a shorter alkyl chain (carbon atom number <8), terminal rings, or electron-deficient groups on the alkyl side chain are beneficial for antifungal potency. Further, bioassay results revealed that the component of 21 in complex 34 dominated the antifungal activity, but the introduction of Cu(II) significantly enhanced its antibacterial activity. The toxicological observations demonstrated that 21 could induce abnormal mitochondrial morphology, loss of mitochondrial membrane potential, and reactive oxygen species (ROS) accumulation in S. sclerotiorum. The enzyme assay results showed that 21 is a moderate promiscuous inhibitor of mitochondrial complexes II and III. Besides, the introduction of Cu(II) to 34 could promote the disruption of the cell membrane and intracellular proteins and the ROS level in Xcc compared with 21. In summary, these results highlight the potential of 34 as a dual antifungal and antibacterial biocide for controlling rape diseases or as a promising candidate for further optimization.

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Section: Resultsmentioning

confidence: 97%

Section: Results and Discussionmentioning

confidence: 97%

Section: D-qsar By Topomermentioning

confidence: 99%

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Chelation of the Optimal Antifungal Pogostone Analogue with Copper(II) to Explore the Dual Antifungal and Antibacterial Agent

Wang,

Yuan,

et al. 2024

J. Agric. Food Chem.

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“…62 This approach has been applied to the first synthesis of racemic germicidine 50 (Scheme 16). 63,64 Germicidine is a 4-hydroxy-2-pyrone isolated from Streptomyces viridochromogenes NRRL B-1551. It was found to inhibit germination of arthrospores of its own producer at concentrations as low as 40 pg mL À1 .…”

Section: Furanones and Pyranonesmentioning

confidence: 99%