A practical total synthesis of wedelolactone

Gou, Hongqian; Zhang, Jungan; Li, Peipei; Li, Chonglong; Wang, Hao; Wei, Hong

doi:10.1080/00397911.2023.2211772

Cited by 1 publication

(3 citation statements)

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“…The aldehydes 53-55, 57, 58, 61, 62, and 65-67 were previously obtained in our laboratory [48]. The 2,4,5-trihydroxybenzaldehyde (60) was obtained by formylation of 1,2,4-trihydroxybenzene (70) with triethyl orthoformate mediated by AlCl 3 in toluene [66].…”

Section: Syntheses and Characterizationmentioning

confidence: 99%

“…Absorption maxima are reported in wavenumbers (cm -1 ). 1 H-NMR and 13 C-NMR spectra were recorded on Jeol 400yh (Tokyo, Japan) (399.78 MHz for 1 H and 100.52 MHz for 13 The literature procedure was adapted for the preparation of hydrazide-hydrazones 1-3, 5-11, 14-25, 27-30 [48], 32 [71], 31, and 33-35 [47]; hydrazides 38-40 [47]; aldehydes 53-55, 58, 61, 62 [48,89], 60 [66], 63 [67], 65 [48,90], 66, 67 [48], and 68 [69]; and phenol 72 [68].…”

Section: Reagents and Materialsmentioning

confidence: 99%

“…Purity and homogeneity of known compounds were confirmed by measuring their m.p. for 1-3, 5-11, 14-21, 24, 25, 27-30 [48], 12 [91], 31, 33-35 [47], 32 [71], 38 [48], 39 [92,93], 40 [47,93], 60 [94], 63 [67], and 68 [69]; boiling points for 65 [48] and 68 [67]; FT-IR spectra for 3 [48], 22 [95], 25 [48], 38, 39 [52], 40 [47], and 68 [69]; 1 H-NMR spectra for 3 [48], 4 [96], 12 [97], 13 [98], 22 [99], 23 [41], 25, 28 [48], 38, 39 [52], 40 [47], 60 [66], 65 [48], and 68 [69]; 13 C-NMR spectra for 3 [48], 4 [96], 22 [95], 25, 28 [48], 38, 39 [52], 40 [47], 65 [48], and 68 [69]; and/or HRMS for 3 [48], 4 [96], 22 [95], 25, and 28 [48] and comparing them with literature data. Two new aroylhydrazide-hydrazones, 26 and 32, were fully characterized.…”

Section: Reagents and Materialsmentioning

confidence: 99%

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4-Hydroxybenzoic Acid-Based Hydrazide–Hydrazones as Potent Growth Inhibition Agents of Laccase-Producing Phytopathogenic Fungi That Are Useful in the Protection of Oilseed Crops

Maniak,

Matyja,

Pląskowska

et al. 2024

Molecules

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The research on new compounds against plant pathogens is still socially and economically important. It results from the increasing resistance of pests to plant protection products and the need to maintain high yields of crops, particularly oilseed crops used to manufacture edible and industrial oils and biofuels. We tested thirty-five semi-synthetic hydrazide–hydrazones with aromatic fragments of natural origin against phytopathogenic laccase-producing fungi such as Botrytis cinerea, Sclerotinia sclerotiorum, and Cerrena unicolor. Among the investigated molecules previously identified as potent laccase inhibitors were also strong antifungal agents against the fungal species tested. The highest antifungal activity showed derivatives of 4-hydroxybenzoic acid and salicylic aldehydes with 3-tert-butyl, phenyl, or isopropyl substituents. S. sclerotiorum appeared to be the most susceptible to the tested compounds, with the lowest IC50 values between 0.5 and 1.8 µg/mL. We applied two variants of phytotoxicity tests for representative crop seeds and selected hydrazide–hydrazones. Most tested molecules show no or low phytotoxic effect for flax and sunflower seeds. Moreover, a positive impact on seed germination infected with fungi was observed. With the potential for application, the cytotoxicity of the hydrazide–hydrazones of choice toward MCF-10A and BALB/3T3 cell lines was lower than that of the azoxystrobin fungicide tested.

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Section: Syntheses and Characterizationmentioning

confidence: 99%