Synthesis and Antibacterial Activities of Osthole Derivatives Containing Phosphonateptide Fragment

doi:10.6023/cjoc202407015

Chinese Journal of Organic Chemistry Previous Articles Next Articles

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含膦酸酯肽的蛇床子素衍生物的合成与抗菌活性

杨家强^a,b,*, 周绪容^a, 陈阳密^a, 佘慧娴^a

^a遵义医科大学药学院遵义 563000;
^b遵义医科大学基础药理教育部重点实验室遵义 563000

收稿日期:2024-08-19 修回日期:2024-10-21
基金资助:
贵州省科技计划(黔科合基础-ZK[2024]一般265)和国家级大学生创新创业训练计划(202310661006)资助项目.

Synthesis and Antibacterial Activities of Osthole Derivatives Containing Phosphonateptide Fragment

Yang Jiaqiang^a,b,*, Zhou Xurong^a, Chen Yangmi^a, She Huixian^a

^aSchool of Pharmacy, Zunyi Medical University, Zunyi 563000;
^bKey Laboratory of Basic Pharmacology of Ministry of Education, Zunyi Medical University, Zunyi 563000

Received:2024-08-19 Revised:2024-10-21
Contact: * E-mail:yjqcn@126.com
Supported by:
Guizhou Provincial Science and Technology Plan (No. Qiankehe Foundation ZK[2024]265) and the National College Students' innovation and entrepreneurship training program(No. 202310661006).

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Abstract

Based on previous research, the structures of osthole derivatives with potential antibacterial activities were optimized. Twenty-one novel derivatives containing phosphonateptide were designed and synthesized, and confirmed by ¹H NMR, ¹³C NMR and elemental analysis. The antibacterial activities against S. aureus, E. coli, methicillin-resistant S. aureus(MRSA) and fluoroquinolone-resistant E. coli(FREC) were evaluated, the results showed that the minimum inhibitory concentration(MIC) of diethyl (E)- ((2-(4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-enamido)acetamido)(3,4,5-trimethoxy phenyl)methyl)phosphonate (5f)was 0.25, 1, 1, 2 μg/mL respectively, and the MIC of diethyl (E)- ((2-(4-(7-methoxy-2-oxo- 2H-chromen-8-yl)-2-methylbut-2- enamido)acetamido)(4-methylthiazol-2-yl)methyl)phosphonate(5u)was 0.25, 2, 1, 2 μg/mL respectively. Its antibacterial activities were superior to the control drugs oxacillin and norfloxacin, which will be further developed as novel candidates for antibacterial drugs. The binding with phosphonateptide can enhance their anti-S. aureus and anti-MRSA activities, and keep significant anti-E. coli and anti-FREC activities.

Key words: osthole derivatives, structural optimization, phosphonateptide, synthesis, antibacterial activity

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Yang Jiaqiang, Zhou Xurong, Chen Yangmi, She Huixian. Synthesis and Antibacterial Activities of Osthole Derivatives Containing Phosphonateptide Fragment[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202407015.

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含膦酸酯肽的蛇床子素衍生物的合成与抗菌活性

Synthesis and Antibacterial Activities of Osthole Derivatives Containing Phosphonateptide Fragment

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