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Synthesis, Structural Characterization, and Biological Activities of 1,3,4- Thiadiazole Derivatives Containing Sulfonylpiperazine Structures.

التفاصيل البيبلوغرافية
العنوان: Synthesis, Structural Characterization, and Biological Activities of 1,3,4- Thiadiazole Derivatives Containing Sulfonylpiperazine Structures.
المؤلفون: Liu YH; National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang, 550025, China., Wang FL; National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang, 550025, China., Ren XL; National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang, 550025, China., Li CK; National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang, 550025, China., Jin LH; National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang, 550025, China., Zhou X; National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang, 550025, China.
المصدر: Chemistry & biodiversity [Chem Biodivers] 2024 Jun; Vol. 21 (6), pp. e202400408. Date of Electronic Publication: 2024 Mar 28.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Verlag Helvetica Chimica Acta Country of Publication: Switzerland NLM ID: 101197449 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1612-1880 (Electronic) Linking ISSN: 16121872 NLM ISO Abbreviation: Chem Biodivers Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Zürich, Switzerland : Hoboken, NJ : Verlag Helvetica Chimica Acta ; Distributed in the USA by Wiley, c2004-
مواضيع طبية MeSH: Thiadiazoles*/chemistry , Thiadiazoles*/pharmacology , Thiadiazoles*/chemical synthesis , Anti-Bacterial Agents*/pharmacology , Anti-Bacterial Agents*/chemical synthesis , Anti-Bacterial Agents*/chemistry , Microbial Sensitivity Tests* , Xanthomonas*/drug effects , Biofilms*/drug effects , Molecular Docking Simulation*, Structure-Activity Relationship ; Piperazines/pharmacology ; Piperazines/chemistry ; Piperazines/chemical synthesis ; Molecular Structure ; Oryza/microbiology
مستخلص: To develop novel bacterial biofilm inhibiting agents, a series of 1,3,4-thiadiazole derivatives containing sulfonylpiperazine structures were designed, synthesized, and characterized using 1 H nuclear magnetic resonance ( 1 H NMR), 13 C nuclear magnetic resonance ( 13 C NMR), and high-resolution mass spectrometry. Meanwhile, their biological activities were evaluated, and the ensuing structure-activity relationships were discussed. The bioassay results showed the substantial antimicrobial efficacy exhibited by most of the compounds. Among them, compound A 24 demonstrated a strong efficacy with an EC 50 value of 7.8 μg/mL in vitro against the Xanthomonas oryzae pv. oryzicola (Xoc) pathogen, surpassing commercial agents thiodiazole copper (31.8 μg/mL) and bismerthiazol (43.3 μg/mL). Mechanistic investigations into its anti-Xoc properties revealed that compound A 24 operates by increasing the permeability of bacterial cell membranes, inhibiting biofilm formation and cell motility, and inducing morphological changes in bacterial cells. Importantly, in vivo tests showed its excellent protective and curative effects on rice bacterial leaf streak. Besides, molecular docking showed that the hydrophobic effect and hydrogen-bond interactions are key factors between the binding of A 24 and AvrRxo1-ORF1. Therefore, these results suggest the utilization of 1,3,4-thiadiazole derivatives containing sulfonylpiperazine structures as a bacterial biofilm inhibiting agent, warranting further exploration in the realm of agrochemical development.
(© 2024 Wiley-VHCA AG, Zurich, Switzerland.)
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معلومات مُعتمدة: 21967006 National Nature Science Foundation of China
فهرسة مساهمة: Keywords: 1,3,4-thiadiazole derivatives; antimicrobial activity; antimicrobial mechanism; sulfonylpiperazine
المشرفين على المادة: 0 (Thiadiazoles)
0 (Anti-Bacterial Agents)
14IAC3GH7G (1,3,4-thiadiazole)
0 (Piperazines)
SCR Organism: Xanthomonas oryzae
تواريخ الأحداث: Date Created: 20240305 Date Completed: 20240618 Latest Revision: 20240621
رمز التحديث: 20240622
DOI: 10.1002/cbdv.202400408
PMID: 38441384
قاعدة البيانات: MEDLINE
الوصف
تدمد:1612-1880
DOI:10.1002/cbdv.202400408