Syntheses and Biological Activities of 1,4-Pentadien-3-oneDerivatives Containing Thioether Triazole Moiety

doi:10.6023/cjoc201903048

Abstract

A series of novel 1,4-pentadien-3-one derivatives containing thioether triazole units were synthesized by introducing triazoles bearing thiol groups into the structures of 1,4-pentadien-3-one. The structures of the newly synthesized compounds were assigned via ¹H NMR, ¹³C NMR and HRMS. Bioassays indicated that some of the compounds showed potential antibacterial activities against X. citri, X. oryzae and R. solanacearum. Among them, compounds F₄, F₆ and F₁₆ demonstrated appreciable inhibitory effect against Xanthomonas axonopodis pv. citri, with half-maximal effective concentration (EC₅₀) values of 16.3, 9.9 and 15.9 μg/mL, which were better than commercial agent bismerthiazol (54.9 μg/mL). Compounds F₁, F₇ and F₁₅ demonstrated appreciable inhibitory effects against Xanthomonas oryzae pv. Oryzae with EC₅₀ values of 9.6, 19.2 and 21.3 μg/mL, which were better than commercial agent bismerthiazol (69.3 μg/mL). Compounds F₃ and F₆also demonstrated appreciable inhibitory effects against Ralstonia solanacearum with EC₅₀ values of 14.2 and 14.5 μg/mL, which were better than commercial agent bismerthiazol (82.6 μg/mL). The possible mechanism of the antibacterial activity of the target compound F₆ against Xanthomonas axonopodis was investigated through scanning electron microscopy.

Key words: 1,4-pentadien-3-one, thioether triazole, biological activity, scanning electron microscope

Cite this article

Chen Ying, Li Pu, Chen Mei, Su Shijun, He Jun, Zhang Min, Liu Liwei, Xue Wei. Syntheses and Biological Activities of 1,4-Pentadien-3-oneDerivatives Containing Thioether Triazole Moiety[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2813-2820.

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Compound	R	X. citri		X. oryzae		R. solanacearum
Compound	R	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL
F₁	Ph	47.0±1.6	36.5±4.0	89.5±0.9	74.3±0.1	54.5±3.4	49.8±5.3
F₂	Thiophen-2-yl	42.4±2.3	39.0±5.0	34.7±0.6	1.5±0.2	32.8±2.1	28.3±0.1
F₃	3,4-(CH₃)₂C₆H₃	57.4±4.1	41.9±2.7	17.7±0.8	10.6±1.4	75.9±1.5	62.4±0.4
F₄	4-NO₂C₆H₄	72.3±5.3	62.8±2.8	58.0±0.5	41.6±1.2	51.6±0.1	47.9±0.5
F₅	4-ClC₆H₄	68.0±0.9	52.3±2.5	60.5±1.1	48.8±0.5	48.3±2.4	35.2±1.6
F₆	4-FC₆H₄	82.5±0.2	78.6±2.9	59.0±4.7	50.6±3.0	76.8±5.4	66.3±3.5
F₇	2,4-(CH₃O)₂C₆H₃	71.3±0.9	63.5±0.4	70.0±0.4	62.9±0.9	53.2±0.6	50.0±3.2
F₈	3-NO₂C₆H₄	66.9±6.4	57.1±1.1	60.1±1.6	51.7±1.8	50.5±3.8	41.7±5.2
F₉	2-ClC₆H₄	72.6±4.3	64.1±2.2	56.2±4.7	47.6±2.6	41.6±0.9	35.2±0.5
F₁₀	4-CH₃OC₆H₄	70.9±2.9	64.5±5.4	61.7±0.9	57.4±2.6	48.3±2.5	32.4±3.5
F₁₁	4-Methylthiazol-5-yl	63.3±5.6	56.5±1.2	46.9±2.8	44.7±0.8	44.9±1.6	36.3±1.3
F₁₂	Furan-2-yl	55.3±1.3	48.1±2.5	68.6±4.2	56.7±0.2	37.4±0.7	23.2±4.8
F₁₃	3,4-(CH₃O)₂C₆H₃	38.5±4.0	25.0±1.6	66.2±0.4	60.4±3.9	54.8±1.9	42.1±1.3
F₁₄	4-BrC₆H₄	73.6±6.1	65.8±2.7	62.2±0.7	54.9±0.4	50.2±0.1	47.1±7.2
F₁₅	2,4-Cl₂C₆H₃	56.7±2.4	45.7±4.9	61.7±0.4	54.9±0.6	55.9±1.1	42.4±0.6
F₁₆	4-CH₃C₆H₄	77.4±4.0	68.7±1.4	53.0±1.9	44.6±0.6	51.0±1.8	33.9±2.3
Bismerthiazol^b	—	59.5±7.7	49.5±5.7	56.0±1.2	33.8±2.0	61.1±6.2	49.5±5.3

Compound	R	X. citri		X. oryzae		R. solanacearum
Compound	R	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL
F₁	Ph	47.0±1.6	36.5±4.0	89.5±0.9	74.3±0.1	54.5±3.4	49.8±5.3
F₂	Thiophen-2-yl	42.4±2.3	39.0±5.0	34.7±0.6	1.5±0.2	32.8±2.1	28.3±0.1
F₃	3,4-(CH₃)₂C₆H₃	57.4±4.1	41.9±2.7	17.7±0.8	10.6±1.4	75.9±1.5	62.4±0.4
F₄	4-NO₂C₆H₄	72.3±5.3	62.8±2.8	58.0±0.5	41.6±1.2	51.6±0.1	47.9±0.5
F₅	4-ClC₆H₄	68.0±0.9	52.3±2.5	60.5±1.1	48.8±0.5	48.3±2.4	35.2±1.6
F₆	4-FC₆H₄	82.5±0.2	78.6±2.9	59.0±4.7	50.6±3.0	76.8±5.4	66.3±3.5
F₇	2,4-(CH₃O)₂C₆H₃	71.3±0.9	63.5±0.4	70.0±0.4	62.9±0.9	53.2±0.6	50.0±3.2
F₈	3-NO₂C₆H₄	66.9±6.4	57.1±1.1	60.1±1.6	51.7±1.8	50.5±3.8	41.7±5.2
F₉	2-ClC₆H₄	72.6±4.3	64.1±2.2	56.2±4.7	47.6±2.6	41.6±0.9	35.2±0.5
F₁₀	4-CH₃OC₆H₄	70.9±2.9	64.5±5.4	61.7±0.9	57.4±2.6	48.3±2.5	32.4±3.5
F₁₁	4-Methylthiazol-5-yl	63.3±5.6	56.5±1.2	46.9±2.8	44.7±0.8	44.9±1.6	36.3±1.3
F₁₂	Furan-2-yl	55.3±1.3	48.1±2.5	68.6±4.2	56.7±0.2	37.4±0.7	23.2±4.8
F₁₃	3,4-(CH₃O)₂C₆H₃	38.5±4.0	25.0±1.6	66.2±0.4	60.4±3.9	54.8±1.9	42.1±1.3
F₁₄	4-BrC₆H₄	73.6±6.1	65.8±2.7	62.2±0.7	54.9±0.4	50.2±0.1	47.1±7.2
F₁₅	2,4-Cl₂C₆H₃	56.7±2.4	45.7±4.9	61.7±0.4	54.9±0.6	55.9±1.1	42.4±0.6
F₁₆	4-CH₃C₆H₄	77.4±4.0	68.7±1.4	53.0±1.9	44.6±0.6	51.0±1.8	33.9±2.3
Bismerthiazol^b	—	59.5±7.7	49.5±5.7	56.0±1.2	33.8±2.0	61.1±6.2	49.5±5.3

Compound	R	Toxic regression equation	r	EC₅₀/(μg?mL^–1)
F₄	4-O₂NC₆H₄	y=0.7252x+4.1219	0.9871	16.3±2.5
F₅	4-ClC₆H₄	y=0.9076x+3.6020	0.9559	34.7±2.3
F₆	4-FC₆H₄	y=0.9529x+4.0511	0.9581	9.9±2.1
F₇	2,4-(CH₃O)₂C₆H₃	y=0.6956x+4.1554	0.9889	16.4±1.0
F₈	3-O₂NC₆H₄	y=0.9427x+3.5545	0.9965	34.2±2.4
F₉	2-ClC₆H₄	y=0.8344x+3.9314	0.9978	19.1±2.7
F₁₀	4-CH₃OC₆H₄	y=0.7527x+4.0683	0.9897	17.3±2.8
F₁₄	4-BrC₆H₄	y=0.8865x+3.8683	0.9899	18.9±2.8
F₁₆	4-CH₃C₆H₄	y=0.9412x+3.8669	0.9965	15.9±1.9
Bismerthiazol^a	—	y=0.8357x+3.5466	0.9876	54.9±1.4

Compound	R	Toxic regression equation	r	EC₅₀/(μg?mL^–1)
F₄	4-O₂NC₆H₄	y=0.7252x+4.1219	0.9871	16.3±2.5
F₅	4-ClC₆H₄	y=0.9076x+3.6020	0.9559	34.7±2.3
F₆	4-FC₆H₄	y=0.9529x+4.0511	0.9581	9.9±2.1
F₇	2,4-(CH₃O)₂C₆H₃	y=0.6956x+4.1554	0.9889	16.4±1.0
F₈	3-O₂NC₆H₄	y=0.9427x+3.5545	0.9965	34.2±2.4
F₉	2-ClC₆H₄	y=0.8344x+3.9314	0.9978	19.1±2.7
F₁₀	4-CH₃OC₆H₄	y=0.7527x+4.0683	0.9897	17.3±2.8
F₁₄	4-BrC₆H₄	y=0.8865x+3.8683	0.9899	18.9±2.8
F₁₆	4-CH₃C₆H₄	y=0.9412x+3.8669	0.9965	15.9±1.9
Bismerthiazol^a	—	y=0.8357x+3.5466	0.9876	54.9±1.4

Compound	R	Toxic regression equation	r	EC₅₀/(μg?mL^–1)
F₁	Ph	y=1.0838x+3.9378	0.9488	9.6±1.9
F₅	4-ClC₆H₄	y=0.7955x+3.7062	0.9066	42.3±0.5
F₇	2,4-(CH₃O)₂C₆H₃	y=0.8195x+3.9491	0.9250	19.2±0.8
F₈	3-O₂NC₆H₄	y=0.8219x+3.6715	0.9099	41.3±1.4
F₁₀	4-CH₃OC₆H₄	y=0.8897x+3.6013	0.9524	37.3±1.5
F₁₂	Furan-2-yl	y=0.9935x+3.5123	0.9899	31.4±2.2
F₁₃	3,4-(CH₃O)₂C₆H₃	y=0.9779x+3.5713	0.9402	28.9±1.4
F₁₄	4-BrC₆H₄	y=0.8431x+3.6698	0.9886	37.8±0.8
F₁₅	2,4-Cl₂C₆H₃	y=0.4375x+4.4190	0.9756	21.3±0.8
Bismerthiazol^a	—	y=2.8364x+0.5935	0.9897	69.3±2.0

含硫醚三唑的1,4-戊二烯-3-酮衍生物合成及生物活性研究