文献类型：期刊文献

英文题名：Novel 2-aminothiazole derivatives incorporating 9-alkyl purine moiety: design, synthesis, crystal structure, and bioactivity evaluation

作者：Bai, Song Wan, Suran Li, Miao Wu, Rong Tang, Shouying Wang, Fang Chen, Lijun Lv, Xiaokang Wei, Xian Feng, Shuang Zhang, Miaohe

第一作者：柏松

通信作者：Bai, S[1];Wan, SR[1];Bai, S[2];Bai, S[3]|[14440437795d317a98a55]柏松;

机构：[1]Guizhou Ind Polytech Coll, Guiyang 550008, Peoples R China;[2]Guizhou Inst Technol, Sch Chem Engn, Guiyang 550003, Peoples R China;[3]Guizhou Univ, Natl Key Lab Green Pesticide, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China

第一机构：Guizhou Ind Polytech Coll, Guiyang 550008, Peoples R China

通信机构：corresponding author), Guizhou Ind Polytech Coll, Guiyang 550008, Peoples R China;corresponding author), Guizhou Inst Technol, Sch Chem Engn, Guiyang 550003, Peoples R China;corresponding author), Guizhou Univ, Natl Key Lab Green Pesticide, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China.|贵州理工学院化学工程学院;贵州理工学院;

年份：2025

外文期刊名：MOLECULAR DIVERSITY

收录：;Scopus(收录号：2-s2.0-105002345821);WOS:【SCI-EXPANDED(收录号:WOS:001465080000001)】；

基金：The authors gratefully acknowledge the Science and Technology Planning Project of Guizhou Province (Grant No. Qian Ke He Ji Chu ZK [2022]Zhong Dian 025), High School Science and Technology Talent Support Project of Guizhou Province, China (Grant No. Qian Jiao He KY Zi [2021]037), Basic Research Project of Guizhou Province (Grant No. Qian Ke He Ji Chu MS [2025]003), High-Level Talent Initial Funding of Guizhou Industry Polytechnic College (Grant No. 2023-RC-01), The Opening Foundation of the Key Laboratory of Green Pesticide and Agricultural Bioengineering, the Ministry of Education, Guizhou University (Grant No. Qian Jiao Ji [2022]433), Guizhou Provincial Department of Education Youth Science and Technology Talent Growth Project (Grant No. Qian Jiao Ji [2024]292 Hao & Grant No. Qian Jiao Ji [2024]293 Hao). Guizhou Industry Polytechnic College Science and Technology Innovation Team Project (Grant No. 2023CXTD03), Guizhou Industry Polytechnic College Faculty-level Research Project (Grant No. 2023ZK10 & Grant No. 2023ZK11), The Young Science and Technology Talents Development Program of Education Department of Guizhou Province (Grant No. Qian Jiao He KY Zi [2022]346 Hao), the academic new seedling cultivation and exploration and innovation project of Guizhou Institute of Technology (Grant No. GZLGXM-20).

语种：英文

外文关键词：2-Aminothiazole derivatives; 9-Alkyl purine; Crystal structure; Antimicrobial activity; Antibacterial mechanisms

摘要：A series of 2-aminothiazole derivatives (3A1-3A30) containing 9-alkyl purine moiety were designed and synthesized to explore novel antibacterial agents with unique structures and potent antibacterial activity. The structures of target compounds were characterized using 1H NMR, 13C NMR, and HRMS techniques. The structure of compound 3A12 was further elucidated through single crystal X-ray diffraction analysis. Results from antibacterial activity tests indicated that compound 3A7 exhibited a significant inhibitory effect on Xanthomonas oryzae pv. oryzicola (Xoc), with an EC50 (half-maximal effective concentration) value of 25.5 mu g/mL, which was more than three times higher than that of the control agent thiodiazole copper (EC50 = 78.4 mu g/mL). Compound 3A25 has a strong inhibitory effect on Xanthomonas axonopodis pv. citric (Xac), with significantly higher activity than thiodiazole copper in terms of EC50 value (47.3 vs 92.1 mu g/mL). Additionally, the EC50 value of compound 3A7 against Pseudomonas syringae pv. actinidiae (Psa) was measured at 57.5 mu g/mL, demonstrating superior efficacy relative to the control agents bismerthiazol (EC50 = 92.9 mu g/mL) and thiodiazole copper (EC50 = 90.2 mu g/mL). The antibacterial mechanism of compound 3A7 was examined through an investigation into the production of exopolysaccharides, alterations in membrane permeability, morphological changes in bacterial cells, and the development of a molecular docking model. Through a 100 ns molecular dynamics (MD) simulation, the stability of the binding between compound 3A7 and the AvrRxo1-ORF1 protein was confirmed. Furthermore, the chemical reactivity of potential bioactive compounds was evaluated using density functional theory (DFT).