Synthesis, Antibacterial and Antifungal Evaluation of Rhodanine Derivatives Bearing Quinoxalinyl Imidazole Moiety as ALK5 Inhibitors

doi:10.6023/cjoc202106015

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4428-4436.DOI: 10.6023/cjoc202106015 Previous Articles Next Articles

ARTICLES

含喹喔啉基咪唑结构的罗丹宁衍生物的合成及其ALK5、抗菌和抗真菌活性研究

韩立卓^a, 赵丽敏^a, 王慧敏^a, 窦桐^a, 郭芳妍^a, 齐浚答^a, 许文博^a, 朴莲荀^a, 金学军^a, 陈芬儿^b, 朴虎日^b, 郑昌吉^b^,^*(), 金成华^a^,^b^,^*()

a 延边大学药学院分子药物研究中心吉林延吉 133002
b 延边大学长白山天然药物教育部重点实验室吉林延吉 133002

收稿日期:2021-06-07 修回日期:2021-07-12 发布日期:2021-08-09
通讯作者: 郑昌吉, 金成华
作者简介:
† 共同第一作者.
基金资助:
国家自然科学基金(8206023)

Synthesis, Antibacterial and Antifungal Evaluation of Rhodanine Derivatives Bearing Quinoxalinyl Imidazole Moiety as ALK5 Inhibitors

Lizhuo Han^a, Limin Zhao^a, Huimin Wang^a, Tong Dou^a, Fangyan Guo^a, Junda Qi^a, Wenbo Xu^a, Lianxun Piao^a, Xuejun Jin^a, Fen'er Chen^b, Huri Piao^b, Changji Zheng^b(), Chenghua Jin^a^,^b()

a Molecular Medicine Research Center, College of Pharmacy, Yanbian University, Yanji, Jilin 133002
b Key Laboratory of Natural Medicines of the Changbai Mountain, Minstry of Education, Yanbian University, Yanji, Jilin 133002

Received:2021-06-07 Revised:2021-07-12 Published:2021-08-09
Contact: Changji Zheng, Chenghua Jin
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(8206023)

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Abstract

Transforming growth factor-β (TGF-β) is overexpressed in many diseases, and is an important target for treating tumors. Two series of 3-substituted-5-((5-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-yl)methylene)-2-thioxo- thiazolidin-4-ones (12, 13a~13e, and 14a~14h) were synthesized and evaluated for their activin receptor-like kinase 5 (ALK5) inhibition activity. Among these compounds, (Z)-6-(5-((5-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol- 2-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)hexanoic acid (13e) showed the highest activity (IC₅₀=0.451 µmol•L^–1) against ALK5 kinase, which had a good selectivity index of >22 against p38α MAP kinase, with 5.0-fold more selectivity than the clinical candidate of LY-2157299. These rhodanine compounds showed good antifungal activity and high selectivity against both Gram-positive and Gram-negative bacteria. These compounds showed similar or higher antifungal activity (MIC=0.5 or 1 µg/mL) to the positive control compound fluconazole (MIC=1 µg/mL).

Key words: rhodanine, TGF-β, quinoxalinyl imidazole, ALK5 inhibitor, antimicrobial, antifungal

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Lizhuo Han, Limin Zhao, Huimin Wang, Tong Dou, Fangyan Guo, Junda Qi, Wenbo Xu, Lianxun Piao, Xuejun Jin, Fen'er Chen, Huri Piao, Changji Zheng, Chenghua Jin. Synthesis, Antibacterial and Antifungal Evaluation of Rhodanine Derivatives Bearing Quinoxalinyl Imidazole Moiety as ALK5 Inhibitors[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4428-4436.

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References 40

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Compd.	R	IC₅₀^a/(μmol•L^–1)		Selectivity index^b
Compd.	R	p38α	ALK5	Selectivity index^b
12	H	>10	3.215	>3
13a	CH₂COOH	4.417	1.027	4
13b	(CH₂)₂COOH	>10	1.137	>8
13c	(CH₂)₃COOH	>10	0.614	>16
13d	(CH₂)₄COOH	>10	2.276	>4
13e	(CH₂)₅COOH	>10	0.451	>22
14a	CH₂(3-methyl- benzoate)	>10	1.783	>5
14b	CH₂(4-benzoic acid)	>10	0.500	>20
14c	CH₂(2-FC₆H₄)	>10	1.709	>5
14d	CH₂(3-FC₆H₄)	>10	0.954	>10
14e	CH₂(4-FC₆H₄)	>10	3.037	>3
14f	CH₂(2-CH₃C₆H₄)	>10	0.494	>20
14g	CH₂(3-CH₃C₆H₄)	>10	5.076	>1
14h	CH₂(4-CH₃C₆H₄)	>10	0.919	>10
2 (LY-2157299)		0.493	0.129	4

Compd.	R	IC₅₀^a/(μmol•L^–1)		Selectivity index^b
Compd.	R	p38α	ALK5	Selectivity index^b
12	H	>10	3.215	>3
13a	CH₂COOH	4.417	1.027	4
13b	(CH₂)₂COOH	>10	1.137	>8
13c	(CH₂)₃COOH	>10	0.614	>16
13d	(CH₂)₄COOH	>10	2.276	>4
13e	(CH₂)₅COOH	>10	0.451	>22
14a	CH₂(3-methyl- benzoate)	>10	1.783	>5
14b	CH₂(4-benzoic acid)	>10	0.500	>20
14c	CH₂(2-FC₆H₄)	>10	1.709	>5
14d	CH₂(3-FC₆H₄)	>10	0.954	>10
14e	CH₂(4-FC₆H₄)	>10	3.037	>3
14f	CH₂(2-CH₃C₆H₄)	>10	0.494	>20
14g	CH₂(3-CH₃C₆H₄)	>10	5.076	>1
14h	CH₂(4-CH₃C₆H₄)	>10	0.919	>10
2 (LY-2157299)		0.493	0.129	4

Compd.	R	Gram-positive strains			Gram-negative strains		Fungus 7535^e
Compd.	R	4220^a	209^b		1924^c	2742^d	Fungus 7535^e
12	H	>64	>64		>64	>64	0.5
13a	CH₂COOH	>64	>64		>64	>64	0.5
13b	(CH₂)₂COOH	>64	>64		>64	64	1
13c	(CH₂)₃COOH	>64	>64		>64	>64	0.5
13d	(CH₂)₄COOH	>64	>64		>64	>64	0.5
13e	(CH₂)₅COOH	>64	>64		>64	>64	>64
14a	CH₂(3-methyl- benzoate)	>64	>64		>64	>64	0.5
14b	CH₂(4-benzoic acid)	>64	>64		>64	>64	0.5
14c	CH₂(2-FC₆H₄)	>64	>64		>64	>64	0.5
14d	CH₂(3-FC₆H₄)	>64	>64		>64	>64	0.5
14e	CH₂(4-FC₆H₄)	>64	>64		>64	>64	0.5
14f	CH₂(2-CH₃C₆H₄)	>64	>64		>64	>64	0.5
14g	CH₂(3-CH₃C₆H₄)	>64	>64		>64	>64	0.5
14h	CH₂(4-CH₃C₆H₄)	>64	>64		>64	>64	0.5
Gatifloxacin	0.25	1		2	1	0.5
Fluconazole	N.D^f	N.D		N.D	N.D	1

Compd.	R	Gram-positive strains			Gram-negative strains		Fungus 7535^e
Compd.	R	4220^a	209^b		1924^c	2742^d	Fungus 7535^e
12	H	>64	>64		>64	>64	0.5
13a	CH₂COOH	>64	>64		>64	>64	0.5
13b	(CH₂)₂COOH	>64	>64		>64	64	1
13c	(CH₂)₃COOH	>64	>64		>64	>64	0.5
13d	(CH₂)₄COOH	>64	>64		>64	>64	0.5
13e	(CH₂)₅COOH	>64	>64		>64	>64	>64
14a	CH₂(3-methyl- benzoate)	>64	>64		>64	>64	0.5
14b	CH₂(4-benzoic acid)	>64	>64		>64	>64	0.5
14c	CH₂(2-FC₆H₄)	>64	>64		>64	>64	0.5
14d	CH₂(3-FC₆H₄)	>64	>64		>64	>64	0.5
14e	CH₂(4-FC₆H₄)	>64	>64		>64	>64	0.5
14f	CH₂(2-CH₃C₆H₄)	>64	>64		>64	>64	0.5
14g	CH₂(3-CH₃C₆H₄)	>64	>64		>64	>64	0.5
14h	CH₂(4-CH₃C₆H₄)	>64	>64		>64	>64	0.5
Gatifloxacin	0.25	1		2	1	0.5
Fluconazole	N.D^f	N.D		N.D	N.D	1

Compd.	MIC (µmol•L^–1)^a	IC₅₀^b^,^c/ (µmol•L^–1)	Compd.	MIC/ (µmol•L^–1)	IC₅₀/ (µmol•L^–1)
12	1.16	39.86	14b	0.89	58.27
13a	1.02	43.26	14c	0.93	53.24
13b	1.99	44.28	14d	0.93	54.96
13c	0.97	46.20	14e	0.93	54.38
13d	0.94	47.36	14f	0.94	55.29
13e	>117.5	48.02	14g	0.94	51.84
14a	0.86	52.86	14h	0.94	53.25

含喹喔啉基咪唑结构的罗丹宁衍生物的合成及其ALK5、抗菌和抗真菌活性研究

Synthesis, Antibacterial and Antifungal Evaluation of Rhodanine Derivatives Bearing Quinoxalinyl Imidazole Moiety as ALK5 Inhibitors

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