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Author: search.filters.author.Poprom, SuriyaphongStart date: 2025

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    Design, Synthesis, and Herbicidal Activity of Novel Dihydrochalcones Derived from Flavokawains and Their Analogs
    (2026-05-01)
    Poprom, Suriyaphong
    ;
    Meesin, Jatuporn
    ;
    Chotpatiwetchkul, Warot
    ;
    Waratchareeyakul, Watcharee
    ;
    Chotsaeng, Nawasit
    Weeds are a major cause of crop production losses worldwide, and environmentally friendly chemical control based on natural or semisynthetic compounds has attracted increasing attention. In this study, flavokawains, a class of natural chalcones, and their analogues were converted into dihydrochalcones (1–27) via Pd-catalyzed hydrogenation. The herbicidal activities of these compounds were evaluated against Chinese amaranth (Amaranthus tricolor) and barnyard grass (Echinochloa crus-galli). Several compounds significantly inhibited seed germination and seedling growth in both species. Herbicidal activity was strongly influenced by the type and position of aromatic substituents, with electron-withdrawing groups and meta substitution providing higher activity. The meta-chloro derivative (15) exhibited the highest activity, markedly inhibiting seed germination as well as shoot and root growth. Further investigation of its mode of action revealed that this compound interfered with seed imbibition, inhibited α-amylase activity, and affected membrane integrity and malondialdehyde (MDA) levels in A. tricolor in a concentration-dependent manner. These findings provide valuable insights for the development of natural product-derived herbicides.
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    Synthesis of pyrimidines from flavokavains and their 2′-hydroxychalcone analogues
    (2026-01-01)
    Songpao, Laksakarn
    ;
    Poprom, Suriyaphong
    ;
    Chotsaeng, Nawasit
    ;
    Meesin, Jatuporn
    Pyrimidines are an important class of heterocycles with diverse biological activities; however, their synthesis from certain substrates remains challenging. In this work, flavokavains and their derivatives were converted into pyrimidines, although initial reactions under basic conditions gave low yields due to a competing intramolecular isomerization to flavanones. Systematic investigation identified solvent as a key factor, with 1,4-dioxane effectively suppressing flavanone formation and enabling the synthesis of a broad range of pyrimidines in moderate to high yields. Both guanidine and benzamidine served as effective nucleophiles, and the reaction was readily scalable to the gram scale. This protocol provides a practical and efficient route to ortho-hydroxyphenyl-substituted pyrimidines, which may serve as useful scaffolds for medicinal chemistry.
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    Allyl Syringate
    (2025-09-01)
    Thimpa, Naruedech
    ;
    Poprom, Suriyaphong
    ;
    Songpao, Laksakarn
    ;
    Chotsaeng, Nawasit
    Syringic acid (1) is a naturally occurring compound with diverse biological activities. Structural modification of syringic acid often enhances its utility; however, the spectroscopic data for several derivatives remain unreported, and the procedures to obtain them can be synthetically challenging. In this study, we report the allylation of syringic acid (1) to afford a novel derivative, allyl syringate (1c). The structure of this compound was confirmed by IR, NMR, and MS spectroscopy and compared with those of closely related derivatives (1a and 1b). These findings provide a useful foundation for further studies on the allylation of syringic acid and related phenolic acid derivatives.