Design and synthesis of abietic acid derivatives containing sulfonamide structure, biological activity and mechanism of action studies

Through active splicing techniques and chemical synthesis methods, we have successfully synthesized a series of novel abietic acid derivatives that combine abietic acid backbone with a sulfonamide group. <i>In vitro</i> tests, these derivatives exhibited remarkable antibacterial activities, especially compound <b>C3</b>. Using three-dimensional quantitative structure–activity relationship (3D-QSAR) analysis, we found that the introduction of electron-absorbing groups at the R<sup>1</sup> position, as well as the introduction of larger groups at the R<sup>2</sup> position, may enhance the antibacterial activity of the target compounds. In addition, studies on the antibacterial mechanism of action of compound <b>C3</b> showed that it could increase the permeability of bacterial membranes, disrupt the cell membrane of <i>Xanthomonas oryzae</i> pv. <i>oryzicola</i> (<i>Xoc</i>), and effectively inhibit bacterial growth. These findings not only elucidate the antibacterial mechanism of <b>C3</b>, but also provide an important scientific basis for the design and development of new antibacterial agents.

Publication Details

Journal
Figshare
Published
2025-01-01
DOI
https://doi.org/10.6084/m9.figshare.29115696
Primary Topic
Biological Activity of Diterpenoids and Biflavonoids
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article
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Design and synthesis of abietic acid derivatives containing sulfonamide structure, biological activity and mechanism of action studies

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Biological Activity of Diterpenoids and Biflavonoids
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Design and synthesis of abietic acid derivatives containing sulfonamide structure, biological activity and mechanism of action studies

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Abstract

Through active splicing techniques and chemical synthesis methods, we have successfully synthesized a series of novel abietic acid derivatives that combine abietic acid backbone with a sulfonamide group. <i>In vitro</i> tests, these derivatives exhibited remarkable antibacterial activities, especially compound <b>C3</b>. Using three-dimensional quantitative structure–activity relationship (3D-QSAR) analysis, we found that the introduction of electron-absorbing groups at the R<sup>1</sup> position, as well as the introduction of larger groups at the R<sup>2</sup> position, may enhance the antibacterial activity of the target compounds. In addition, studies on the antibacterial mechanism of action of compound <b>C3</b> showed that it could increase the permeability of bacterial membranes, disrupt the cell membrane of <i>Xanthomonas oryzae</i> pv. <i>oryzicola</i> (<i>Xoc</i>), and effectively inhibit bacterial growth. These findings not only elucidate the antibacterial mechanism of <b>C3</b>, but also provide an important scientific basis for the design and development of new antibacterial agents.

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Biological Activity of Diterpenoids and Biflavonoids
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Design and synthesis of abietic acid derivatives containing sulfonamide structure, biological activity and mechanism of action studies · Figshare (2025) | TGRS Research Map | TGRS