Synthesis and Antibacterial Activities of Osthole Derivatives Containing Phosphonateptide Fragment

doi:10.6023/cjoc202407015

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (4): 1306-1314.DOI: 10.6023/cjoc202407015 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^*(), 周绪容, 陈阳密, 佘慧娴

遵义医科大学药学院基础药理教育部重点实验室贵州遵义 563000

收稿日期:2024-08-19 修回日期:2024-10-21 发布日期:2024-10-29
基金资助:
贵州省科技计划(黔科合基础-ZK[2024]一般265); 国家级大学生创新创业训练计划(202310661006)

Synthesis and Antibacterial Activities of Osthole Derivatives Containing Phosphonateptide Fragment

Jiaqiang Yang(), Xurong Zhou, Yangmi Chen, Huixian She

Key Laboratory of Basic Pharmacology of Ministry of Education, School of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000

Received:2024-08-19 Revised:2024-10-21 Published:2024-10-29
Contact: * E-mail: yjqcn@126.com
Supported by:
Guizhou Provincial Science and Technology Plan (Qiankehe Foundation ZK[2024]265); National College Students? Innovation and Entrepreneurship Training Program(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. 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 concentrations (MICs) 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) were 0.25, 1.00, 1.00, 2.00 μg/mL respectively, and the MICs 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) were 0.25, 2.00, 1.00, 2.00 μg/mL, respectively. Its antibacterial activities were superior to the control drugs of 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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Jiaqiang Yang, Xurong Zhou, Yangmi Chen, Huixian She. Synthesis and Antibacterial Activities of Osthole Derivatives Containing Phosphonateptide Fragment[J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1306-1314.

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Compd.	MIC/(μg•mL^－1)
Compd.	S. aureus	E. coli	MRSA	FREC
5a	128	128	128	>128
5b	64	128	128	>128
5c	128	>128	128	>128
5d	16	32	32	32
5e	64	64	64	128
5f	0.25	1	1	2
5g	>128	>128	>128	>128
5h	>128	>128	>128	>128
5i	64	128	64	128
5j	>128	>128	>128	>128
5k	>128	>128	>128	>128
5l	>128	>128	>128	>128
5m	128	>128	>128	>128
5n	0.5	2	2	2
5o	>128	>128	>128	>128
5p	>128	>128	>128	>128
5q	16	16	16	64
5r	2	4	4	8
5s	32	64	32	64
5t	16	128	32	128
5u	0.25	2	1	2
Oxacillin	0.5	16	256	64
Norfloxacin	1	4	128	>128

Compd.	MIC/(μg•mL^－1)
Compd.	S. aureus	E. coli	MRSA	FREC
5a	128	128	128	>128
5b	64	128	128	>128
5c	128	>128	128	>128
5d	16	32	32	32
5e	64	64	64	128
5f	0.25	1	1	2
5g	>128	>128	>128	>128
5h	>128	>128	>128	>128
5i	64	128	64	128
5j	>128	>128	>128	>128
5k	>128	>128	>128	>128
5l	>128	>128	>128	>128
5m	128	>128	>128	>128
5n	0.5	2	2	2
5o	>128	>128	>128	>128
5p	>128	>128	>128	>128
5q	16	16	16	64
5r	2	4	4	8
5s	32	64	32	64
5t	16	128	32	128
5u	0.25	2	1	2
Oxacillin	0.5	16	256	64
Norfloxacin	1	4	128	>128

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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