含1,3,4-噻二唑结构的查尔酮缩氨基脲类化合物的合成及抗细菌活性

doi:10.7503/cjcu20180081

高等学校化学学报 ›› 2018, Vol. 39 ›› Issue (8): 1683.doi: 10.7503/cjcu20180081

含1,3,4-噻二唑结构的查尔酮缩氨基脲类化合物的合成及抗细菌活性

万金林¹, 巫受群¹, 甘宜远², 孟娇², 王贞超²(), 欧阳贵平²()

1.绿色农药与农业生物工程国家重点实验室培育基地, 绿色农药与农药生物工程教育部重点实验室,贵州大学精细化工研究开发中心, 2. 药学院, 贵阳 550025

收稿日期:2018-01-25 出版日期:2018-08-10 发布日期:2018-05-27
作者简介:联系人简介: 欧阳贵平, 男, 博士, 教授, 博士生导师, 主要从事新农药和新医药创制方面的研究. E-mail: oygp710@163.com; 王贞超, 女, 博士, 副教授, 主要从事新农药和新医药创制方面的研究. E-mail: wzc.4884@163.com
基金资助:
贵州省科技计划项目(批准号: 20161055)、贵州省教育厅青年科技人才成长项目(批准号: 黔教合KY字[2017]115)和药用植物功效与利用国家重点实验室资助项目(批准号: 201707)资助.

Synthesis and Antibacterial Activities Evaluation of Chalconesemicarbazone Derivatives Bearing 1,3,4-Thiadiazole Moiety^†

WAN Jinlin¹, WU Shouqun¹, GAN Yiyuan², MENG Jiao², WANG Zhenchao2*(), OUYANG Guiping2*()

1. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research of Fine Chemicals,2. College of Pharmacy, Guizhou University, Guiyang 550025, China

Received:2018-01-25 Online:2018-08-10 Published:2018-05-27
Supported by:
† Supported by the Guizhou Provincial Science and Technology Program of China(No. 20161055), the Young Talents Scientific Research Foundation of Guizhou Education Department of China(No. KY[2017]115) and the Project of State Key Laboratory of Functions and Applications of Medicinal Plants of China(No. 201707).

摘要/Abstract

摘要：

以苯甲醛和1,3,4-噻二唑为起始原料, 设计合成了一系列新颖的含1,3,4-噻二唑结构的查尔酮缩氨基脲类化合物. 利用核磁共振波谱(NMR)和高分辨质谱(HRMS)对其结构进行了确证. 初步抑菌活性测试结果表明, 该类化合物对水稻白叶枯病菌(X. oryzae)、烟草青枯病菌(R. solanacearum)和柑橘溃疡病菌(X. citri)均表现出一定的抑制活性, 其中化合物7h和7i在浓度为100 μg/mL时, 对以上3种植物病菌的抑制率均达到100%, EC₅₀值分别为15.13, 30.90, 24.49和21.33, 24.54, 14.79 μg/mL, 均超过对照药叶枯唑(EC₅₀值分别为92.23, 58.88和123.02 μg/mL).

关键词: 1,3,4-噻二唑, 查尔酮缩氨基脲, 抑菌活性

Abstract:

A series of chalconesemicarbazone derivatives bearing a 1,3,4-thiadiazole moiety was designed and synthesized from benzaldehyde and 1,3,4-thiadiazole. All the target compounds were characterized by means of nuclear magnetic resonance and high resolution mass spectrometer. The preliminary bioassay results indicated that all the title compounds exhibited a certain antibacterial activities in vitro against Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum and Xanthomonas axonopodis pv. citri. Especially, compounds 7j and 7k displayed excellent antibacterial activities(100%) against the above three plant pathogenic bacteria at a concentration of 100 μg/mL. And the corresponding EC₅₀(50% effective concentration) values were 15.13, 30.90, 24.49 and 21.33, 24.54, 14.79 μg/mL, respectively, which were superior to the commercial antibacterial agent bismerthiazol(92.23, 58.88 and 123.02 μg/mL).

Key words: 1,3,4-Thiadiazole, Chalconesemicarbazone, Antibacterial activity

TrendMD:

万金林, 巫受群, 甘宜远, 孟娇, 王贞超, 欧阳贵平. 含1,3,4-噻二唑结构的查尔酮缩氨基脲类化合物的合成及抗细菌活性. 高等学校化学学报, 2018, 39(8): 1683.

WAN Jinlin, WU Shouqun, GAN Yiyuan, MENG Jiao, WANG Zhenchao*, OUYANG Guiping*. Synthesis and Antibacterial Activities Evaluation of Chalconesemicarbazone Derivatives Bearing 1,3,4-Thiadiazole Moiety^†. Chem. J. Chinese Universities, 2018, 39(8): 1683.

图/表 7

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Compd.	m. p./℃	Compd.	m. p./℃	Compd.	m. p./℃
2a	157—159(158^[20])	2h	119—121	2o	177—179
2b	151—153(151—152^[21])	2i	128—130(128—129^[22])	2p	136—137(136—137^[25])
2c	138—140(138—139^[22])	2j	181—183(181—182^[23])	2q	116—118(117—119^[25])
2d	167—169(168—169^[22])	2k	143—145(145—146^[23])	2r	103—105
2e	100—102	2l	148—150(149—150^[23])	2s	112—113(112—115^[25])
2f	148—150	2m	104—106
2g	151—153	2n	133—135(133—134^[24])

Compd.	m. p./℃	Compd.	m. p./℃	Compd.	m. p./℃
2a	157—159(158^[20])	2h	119—121	2o	177—179
2b	151—153(151—152^[21])	2i	128—130(128—129^[22])	2p	136—137(136—137^[25])
2c	138—140(138—139^[22])	2j	181—183(181—182^[23])	2q	116—118(117—119^[25])
2d	167—169(168—169^[22])	2k	143—145(145—146^[23])	2r	103—105
2e	100—102	2l	148—150(149—150^[23])	2s	112—113(112—115^[25])
2f	148—150	2m	104—106
2g	151—153	2n	133—135(133—134^[24])

Compd.	m. p./℃	HRMS(calcd.)^, m/z*	¹H NMR(DMSO, 400 MHz), δ
3a	170—172	344.0517(344.0522)	12.86(s, 1H), 7.48—7.38(m, 4H), 7.36—7.30(m, 3H), 7.29—7.25(m, 3H), 4.48(s, 2H)
3b	141—143	378.0130(378.0132)	12.88(s, 1H), 7.52—7.47(m, 2H), 7.44(d, J=8.1 Hz, 2H), 7.36—7.25(m, 5H), 4.55(s, 2H)
3c	185—187	378.0122(378.0132)	12.89(s, 1H), 7.50(d, J=1.4 Hz, 1H), 7.48—7.43(m, 2H), 7.40—7.30(m, 4H), 7.30—7.26(m, 2H), 4.49(s, 2H)
3d	172—174	378.0129(378.0132)	12.88(s, 1H), 7.48—7.41(m, 4H), 7.41—7.36(m, 2H), 7.34—7.25(m, 3H), 4.48(s, 2H)
Compd.	m. p./℃	HRMS(calcd.)^, m/z*	¹H NMR(DMSO, 400 MHz), δ
3e	137—139	374.0620(374.0628)	12.88(s, 1H), 7.45(t, J=7.7 Hz, 2H), 7.35—7.24(m, 5H), 7.01(d, J=8.1 Hz, 1H), 6.89(t, J=7.4 Hz, 1H), 4.41(s, 2H), 3.80(s, 3H)
3f	139—141	374.0620(374.0628)	12.86(s, 1H), 7.45(t, J=7.9 Hz, 2H), 7.34—7.21(m, 4H), 6.98(t, J=5.6 Hz, 2H), 6.85(dd, J=8.2, 2.1 Hz, 1H), 4.45(s, 2H), 3.73(s, 3H)
3g	199—201	374.0619(374.0628)	12.83(s, 1H), 7.48—7.42(m, 2H), 7.35—7.28(m, 5H), 7.28—7.24(m, 2H), 4.42(s, 2H), 3.73(s, 3H)
3h	137—139	358.0668(358.0678)	12.84(s, 1H), 7.51—7.40(m, 2H), 7.33—7.25(m, 4H), 7.23—7.17(m, 2H), 7.16—7.10(m, 1H), 4.49(s, 2H), 2.37(s, 3H)
3i	152—154	358.0671(358.0678)	12.88(s, 1H), 7.50—7.41(m, 2H), 7.33—7.25(m, 3H), 7.21(t, J=9.0, 2.7 Hz, 3H), 7.08(d, J=6.4 Hz, 1H), 4.44(s, 2H, CH₂), 2.27(s, 3H, CH₃)
3j	187—189	358.0669(358.0678)	12.85(s, 1H), 7.45(t, J=7.8 Hz, 2H), 7.34—7.24(m, 5H), 7.13(d, J=7.6 Hz, 2H), 4.43(s, 2H), 2.27(s, 3H)
3k	144—146	362.0421(362.0428)	12.90(s, 1H), 7.49—7.42(m, 3H), 7.38—7.25(m, 4H), 7.19—7.12(m, 2H), 4.48(s, 2H)
3l	161—163	362.0423(362.0428)	12.86(s, 1H), 7.48—7.42(m, 4H), 7.34—7.25(m, 3H), 7.23—7.12(m, 2H), 4.48(s, 2H)
3m	120—122	369.0467(369.0474)	12.90(s, 1H), 7.85(dd, J=7.7, 0.9 Hz, 1H), 7.70—7.61(m, 2H), 7.52—7.42(m, 3H), 7.34—7.25(m, 3H), 4.62(s, 2H)
3n	162—164	411.9735(411.9743)	12.92(s, 1H), 7.63(d, J=12.1 Hz, 1H), 7.53(d, J=8.3 Hz, 1H), 7.46(t, J=7.0 Hz, 2H), 7.39(t, J=7.8 Hz, 1H), 7.30(dd, J=16.2, 8.3 Hz, 3H), 4.53(s, 2H)
3o	159—161	268.0204(268.0209)	12.85(s, 1H), 7.45(t, J=7.6 Hz, 2H), 7.30(dd, J=16.4, 7.1 Hz, 3H), 2.71(s, 3H)
3p	206—209	282.0361(282.0365)	8.46(s, 1H), 3.18(q, J=7.3 Hz, 2H), 1.33(t, J=7.3 Hz, 3H)
3q	190—192	296.0518(296.0522)	8.46(s, 1H), 3.15(t, J=7.1 Hz, 2H), 1.76—1.63(m, 2H), 0.98(t, J=7.3 Hz, 3H)
3r	181—183	310.0669(310.0678)	8.46(s, 1H), 3.17(t, J=7.3 Hz, 2H), 1.71—1.60(m, 2H), 1.46—1.35(m, 2H), 0.89(t, J=7.4 Hz, 3H)
3s	108—110	324.0826(324.0835)	12.86(s, 1H), 7.49—7.42(m, 2H), 7.34—7.25(m, 3H), 3.20(t, J=14.6 Hz, 2H), 1.77—1.61(m, 2H), 1.42—1.24(m, 4H), 0.86(t, J=7.2 Hz, 3H)
4a	196—198	282.0469(282.0478)	8.45(s, 1H), 7.41—7.37(m, 2H), 7.35—7.30(m, 2H), 7.29—7.23(m, 1H), 4.43(s, 2H)
4b	195—197	337.9907(337.9908)	8.51(s, 1H), 7.51—7.46(m, 2H), 7.37—7.27(m, 2H), 4.51(s, 2H)
4c	185—187	316.0082(316.0088)	8.45(s, 1H), 7.47(s, 1H), 7.38—7.30(m, 3H), 4.44(s, 2H)
4d	212—213	337.9905(337.9908)	8.46(s, 1H), 7.43—7.36(m, 4H), 4.43(s, 2H)
4e	201—203	312.0577(312.0583)	8.49(s, 1H), 7.29(t, J=7.9 Hz, 2H), 7.01(d, J=8.1 Hz, 1H), 6.89(t, J=7.4 Hz, 1H), 4.37(s, 2H), 3.81(s, 3H)
4f	191—194	312.0579(312.0583)	8.45(s, 1H), 7.24(t, J=8.0 Hz, 1H), 6.95(d, J=7.4 Hz, 2H), 6.84(ddd, J=8.2, 2.5, 1.0 Hz, 1H), 4.40(s, 2H), 3.73(s, 3H)
4g	211—213	312.0577(312.0583)	8.45(s, 1H), 7.31(d, J=8.7 Hz, 2H), 6.88(d, J=8.7 Hz, 2H), 4.38(s, 2H), 3.73(s, 3H)
4h	200—202	296.0631(296.0634)	8.48(s, 1H), 7.29(d, J=7.3 Hz, 1H), 7.20(d, J=3.7 Hz, 2H), 7.15(dd, J=11.0, 5.7 Hz, 1H), 4.44(s, 2H), 2.37(s, 3H)
4i	207—209	296.0632(296.0634)	8.44(s, 1H), 7.23—7.15(m, 3H), 7.08(d, J=7.3 Hz, 1H), 4.39(s, 2H), 2.28(s, 3H)
4j	189—192	318.0450(318.0454)	8.46(s, 1H), 7.27(d, J=8.0 Hz, 2H), 7.13(d, J=7.8 Hz, 2H), 4.39(s, 2H), 2.27(s, 3H)
4k	171—173	300.0377(300.0384)	8.48(s, 1H), 7.43(t, J=7.7 Hz, 1H), 7.35(dt, J=13.6, 6.6 Hz, 2H), 7.24—7.13(m, 3H), 4.43(s, 2H)
4l	197—199	300.0377(300.0384)	8.48(s, 1H), 7.46—7.41(m, 2H), 7.19—7.12(m, 2H), 4.44(s, 2H)
4m	188—190	307.0425(307.0430)	8.51(s, 1H), 7.85(dd, J=7.7, 1.0 Hz, 1H), 7.69—7.65(m, 1H), 7.64—7.59(m, 1H), 7.49(m, 1H), 4.58(s, 2H)
4n	183—185	371.9517(371.9518)	7.65(d, J=2.2 Hz, 1H), 7.48(d, J=8.3 Hz, 1H), 7.40(dd, J=8.3, 2.1 Hz, 1H), 4.47(s, 2H)
4o	209—211	228.9980(228.9984)	8.46(s, 1H), 2.68(s, 3H)
Compd.	m. p./℃	HRMS(calcd.)^, m/z*	¹H NMR(DMSO, 400 MHz), δ
4p	206—209	220.0320(220.0321)	8.46(s, 1H), 3.18(q, J=7.3 Hz, 2H), 1.33(t, J=7.3 Hz, 3H)
4q	190—192	234.0475(234.0478)	8.46(s, 1H), 3.15(t, J=7.1 Hz, 2H), 1.76—1.63(m, 2H), 0.98(t, J=7.3 Hz, 3H)
4r	181—183	248.0631(248.0634)	8.46(s, 1H), 3.17(t, J=7.3 Hz, 2H), 1.71—1.60(m, 2H), 1.46—1.40(m, 2H), 0.89(t, J=7.4 Hz, 3H)
4s	194—196	262.0784(262.0791)	8.45(s, 1H), 3.16(t, J=7.3 Hz, 2H), 1.69—1.64(m, 2H), 1.43—1.24(m, 4H, CH₂), 0.86(t, J=7.2 Hz, 3H)
6	223—225	180.0210(180.0211)	13.05(s, 1H), 9.99(s, 1H), 8.11—8.01(m, 1H), 7.45—7.38(m, 1H), 7.28—7.20(m, 2H)

Compd.	m. p./℃	HRMS(calcd.)^, m/z*	¹H NMR(DMSO, 400 MHz), δ
3a	170—172	344.0517(344.0522)	12.86(s, 1H), 7.48—7.38(m, 4H), 7.36—7.30(m, 3H), 7.29—7.25(m, 3H), 4.48(s, 2H)
3b	141—143	378.0130(378.0132)	12.88(s, 1H), 7.52—7.47(m, 2H), 7.44(d, J=8.1 Hz, 2H), 7.36—7.25(m, 5H), 4.55(s, 2H)
3c	185—187	378.0122(378.0132)	12.89(s, 1H), 7.50(d, J=1.4 Hz, 1H), 7.48—7.43(m, 2H), 7.40—7.30(m, 4H), 7.30—7.26(m, 2H), 4.49(s, 2H)
3d	172—174	378.0129(378.0132)	12.88(s, 1H), 7.48—7.41(m, 4H), 7.41—7.36(m, 2H), 7.34—7.25(m, 3H), 4.48(s, 2H)
Compd.	m. p./℃	HRMS(calcd.)^, m/z*	¹H NMR(DMSO, 400 MHz), δ
3e	137—139	374.0620(374.0628)	12.88(s, 1H), 7.45(t, J=7.7 Hz, 2H), 7.35—7.24(m, 5H), 7.01(d, J=8.1 Hz, 1H), 6.89(t, J=7.4 Hz, 1H), 4.41(s, 2H), 3.80(s, 3H)
3f	139—141	374.0620(374.0628)	12.86(s, 1H), 7.45(t, J=7.9 Hz, 2H), 7.34—7.21(m, 4H), 6.98(t, J=5.6 Hz, 2H), 6.85(dd, J=8.2, 2.1 Hz, 1H), 4.45(s, 2H), 3.73(s, 3H)
3g	199—201	374.0619(374.0628)	12.83(s, 1H), 7.48—7.42(m, 2H), 7.35—7.28(m, 5H), 7.28—7.24(m, 2H), 4.42(s, 2H), 3.73(s, 3H)
3h	137—139	358.0668(358.0678)	12.84(s, 1H), 7.51—7.40(m, 2H), 7.33—7.25(m, 4H), 7.23—7.17(m, 2H), 7.16—7.10(m, 1H), 4.49(s, 2H), 2.37(s, 3H)
3i	152—154	358.0671(358.0678)	12.88(s, 1H), 7.50—7.41(m, 2H), 7.33—7.25(m, 3H), 7.21(t, J=9.0, 2.7 Hz, 3H), 7.08(d, J=6.4 Hz, 1H), 4.44(s, 2H, CH₂), 2.27(s, 3H, CH₃)
3j	187—189	358.0669(358.0678)	12.85(s, 1H), 7.45(t, J=7.8 Hz, 2H), 7.34—7.24(m, 5H), 7.13(d, J=7.6 Hz, 2H), 4.43(s, 2H), 2.27(s, 3H)
3k	144—146	362.0421(362.0428)	12.90(s, 1H), 7.49—7.42(m, 3H), 7.38—7.25(m, 4H), 7.19—7.12(m, 2H), 4.48(s, 2H)
3l	161—163	362.0423(362.0428)	12.86(s, 1H), 7.48—7.42(m, 4H), 7.34—7.25(m, 3H), 7.23—7.12(m, 2H), 4.48(s, 2H)
3m	120—122	369.0467(369.0474)	12.90(s, 1H), 7.85(dd, J=7.7, 0.9 Hz, 1H), 7.70—7.61(m, 2H), 7.52—7.42(m, 3H), 7.34—7.25(m, 3H), 4.62(s, 2H)
3n	162—164	411.9735(411.9743)	12.92(s, 1H), 7.63(d, J=12.1 Hz, 1H), 7.53(d, J=8.3 Hz, 1H), 7.46(t, J=7.0 Hz, 2H), 7.39(t, J=7.8 Hz, 1H), 7.30(dd, J=16.2, 8.3 Hz, 3H), 4.53(s, 2H)
3o	159—161	268.0204(268.0209)	12.85(s, 1H), 7.45(t, J=7.6 Hz, 2H), 7.30(dd, J=16.4, 7.1 Hz, 3H), 2.71(s, 3H)
3p	206—209	282.0361(282.0365)	8.46(s, 1H), 3.18(q, J=7.3 Hz, 2H), 1.33(t, J=7.3 Hz, 3H)
3q	190—192	296.0518(296.0522)	8.46(s, 1H), 3.15(t, J=7.1 Hz, 2H), 1.76—1.63(m, 2H), 0.98(t, J=7.3 Hz, 3H)
3r	181—183	310.0669(310.0678)	8.46(s, 1H), 3.17(t, J=7.3 Hz, 2H), 1.71—1.60(m, 2H), 1.46—1.35(m, 2H), 0.89(t, J=7.4 Hz, 3H)
3s	108—110	324.0826(324.0835)	12.86(s, 1H), 7.49—7.42(m, 2H), 7.34—7.25(m, 3H), 3.20(t, J=14.6 Hz, 2H), 1.77—1.61(m, 2H), 1.42—1.24(m, 4H), 0.86(t, J=7.2 Hz, 3H)
4a	196—198	282.0469(282.0478)	8.45(s, 1H), 7.41—7.37(m, 2H), 7.35—7.30(m, 2H), 7.29—7.23(m, 1H), 4.43(s, 2H)
4b	195—197	337.9907(337.9908)	8.51(s, 1H), 7.51—7.46(m, 2H), 7.37—7.27(m, 2H), 4.51(s, 2H)
4c	185—187	316.0082(316.0088)	8.45(s, 1H), 7.47(s, 1H), 7.38—7.30(m, 3H), 4.44(s, 2H)
4d	212—213	337.9905(337.9908)	8.46(s, 1H), 7.43—7.36(m, 4H), 4.43(s, 2H)
4e	201—203	312.0577(312.0583)	8.49(s, 1H), 7.29(t, J=7.9 Hz, 2H), 7.01(d, J=8.1 Hz, 1H), 6.89(t, J=7.4 Hz, 1H), 4.37(s, 2H), 3.81(s, 3H)
4f	191—194	312.0579(312.0583)	8.45(s, 1H), 7.24(t, J=8.0 Hz, 1H), 6.95(d, J=7.4 Hz, 2H), 6.84(ddd, J=8.2, 2.5, 1.0 Hz, 1H), 4.40(s, 2H), 3.73(s, 3H)
4g	211—213	312.0577(312.0583)	8.45(s, 1H), 7.31(d, J=8.7 Hz, 2H), 6.88(d, J=8.7 Hz, 2H), 4.38(s, 2H), 3.73(s, 3H)
4h	200—202	296.0631(296.0634)	8.48(s, 1H), 7.29(d, J=7.3 Hz, 1H), 7.20(d, J=3.7 Hz, 2H), 7.15(dd, J=11.0, 5.7 Hz, 1H), 4.44(s, 2H), 2.37(s, 3H)
4i	207—209	296.0632(296.0634)	8.44(s, 1H), 7.23—7.15(m, 3H), 7.08(d, J=7.3 Hz, 1H), 4.39(s, 2H), 2.28(s, 3H)
4j	189—192	318.0450(318.0454)	8.46(s, 1H), 7.27(d, J=8.0 Hz, 2H), 7.13(d, J=7.8 Hz, 2H), 4.39(s, 2H), 2.27(s, 3H)
4k	171—173	300.0377(300.0384)	8.48(s, 1H), 7.43(t, J=7.7 Hz, 1H), 7.35(dt, J=13.6, 6.6 Hz, 2H), 7.24—7.13(m, 3H), 4.43(s, 2H)
4l	197—199	300.0377(300.0384)	8.48(s, 1H), 7.46—7.41(m, 2H), 7.19—7.12(m, 2H), 4.44(s, 2H)
4m	188—190	307.0425(307.0430)	8.51(s, 1H), 7.85(dd, J=7.7, 1.0 Hz, 1H), 7.69—7.65(m, 1H), 7.64—7.59(m, 1H), 7.49(m, 1H), 4.58(s, 2H)
4n	183—185	371.9517(371.9518)	7.65(d, J=2.2 Hz, 1H), 7.48(d, J=8.3 Hz, 1H), 7.40(dd, J=8.3, 2.1 Hz, 1H), 4.47(s, 2H)
4o	209—211	228.9980(228.9984)	8.46(s, 1H), 2.68(s, 3H)
Compd.	m. p./℃	HRMS(calcd.)^, m/z*	¹H NMR(DMSO, 400 MHz), δ
4p	206—209	220.0320(220.0321)	8.46(s, 1H), 3.18(q, J=7.3 Hz, 2H), 1.33(t, J=7.3 Hz, 3H)
4q	190—192	234.0475(234.0478)	8.46(s, 1H), 3.15(t, J=7.1 Hz, 2H), 1.76—1.63(m, 2H), 0.98(t, J=7.3 Hz, 3H)
4r	181—183	248.0631(248.0634)	8.46(s, 1H), 3.17(t, J=7.3 Hz, 2H), 1.71—1.60(m, 2H), 1.46—1.40(m, 2H), 0.89(t, J=7.4 Hz, 3H)
4s	194—196	262.0784(262.0791)	8.45(s, 1H), 3.16(t, J=7.3 Hz, 2H), 1.69—1.64(m, 2H), 1.43—1.24(m, 4H, CH₂), 0.86(t, J=7.2 Hz, 3H)
6	223—225	180.0210(180.0211)	13.05(s, 1H), 9.99(s, 1H), 8.11—8.01(m, 1H), 7.45—7.38(m, 1H), 7.28—7.20(m, 2H)

Compd.	Appearance	Yield(%)	m. p. /℃	HRMS(calcd.), m/z[M+H]⁺
7a	White solid	85	189—191	396.0940(396.0947)
7b	White solid	83	180—181	430.0548(430.0558)
7c	White solid	78	172—173	430.0547(430.0558)
7d	White solid	74	200—201	430.0549(430.0558)
7e	White solid	83	173—175	426.1042(426.1053)
7f	White solid	81	159—161	426.1042(426.1053)
7g	White solid	76	177—178	426.1043(426.1053)
7h	White solid	90	172—174	410.1097(410.1104)
7i	White solid	89	171—173	410.1099(410.1104)
7j	White solid	70	173—175	410.1101(410.1104)
7k	White solid	84	167—168	414.0841(414.0853)
7l	White solid	79	210—211	414.0843(414.0853)
7m	Yellow solid	86	165—167	421.0889(421.0899)
7n	Yellow solid	79	185—187	464.0161(464.0168)
7o	Yellow solid	77	189—191	320.0641(320.0634)
7p	Yellow solid	83	197—199	334.0784(334.0791)
7q	Yellow solid	82	184—186	348.0938(348.0947)
7r	Yellow solid	81	138—140	362.1095(362.1104)
7s	Yellow solid	48	139—141	376.1250(376.1260)

含1,3,4-噻二唑结构的查尔酮缩氨基脲类化合物的合成及抗细菌活性

Synthesis and Antibacterial Activities Evaluation of Chalconesemicarbazone Derivatives Bearing 1,3,4-Thiadiazole Moiety^†

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Compd.	¹H NMR(DMSO, 400 MHz), δ	¹³C NMR(DMSO, 100 MHz), δ
7a	11.17(d, J=127.5 Hz, 2H), 7.85(d, J=8.0 Hz, 1H), 7.57(d, J=7.3 Hz, 2H), 7.41(dt, J=7.5, 3.9 Hz, 4H), 7.38—7.31(m, 3H), 7.30—7.24(m, 1H), 7.08—6.95(m, 2H), 4.48(s, 2H)	160.8,158.0, 152.6, 146.2, 138.9,137.2, 136.4, 129.4, 129.0, 128.0, 127.4, 125.6, 38.1
7b	11.23(d, J=129.6 Hz, 2H), 7.87(d, J=7.4 Hz, 1H), 7.58(d, J=7.4 Hz, 2H), 7.53—7.48(m, 2H), 7.41(t, J=7.4 Hz, 2H), 7.33(ddd, J=12.3, 6.0, 2.3 Hz, 3H), 7.08—6.97(m, 2H), 4.55(s, 2H)	161.2, 157.1, 152.5, 146.2, 138.9, 136.3, 134.7, 133.8, 131.9, 130.1, 129.3, 127.8, 127.4, 125.6, 36.3
7c	11.22(d, J=118.1 Hz, 2H), 7.87(d, J=7.3 Hz, 1H), 7.58(d, J=7.4 Hz, 2H), 7.50(s, 1H), 7.43—7.33(m, 6H), 7.08—6.95(m, 2H), 4.49(s, 2H)	161.0, 157.4, 152.5, 146.1, 140.1, 138.9, 136.3, 133.5, 130.8, 129.3, 128.2, 127.9, 127.4, 125.6, 37.2
Compd.	¹H NMR(DMSO, 400 MHz), δ	¹³C NMR(DMSO, 100 MHz), δ
7d	11.20(d, J=130.9 Hz, 2H), 7.86(d, J=7.9 Hz, 1H), 7.57(d, J=7.3 Hz, 2H), 7.42(td, J=8.4, 1.6 Hz, 6H), 7.34(d, J=7.2 Hz, 1H), 7.08—6.95(m, 2H), 4.48(s, 2H)	160.9, 157.5, 152.5, 146.1, 138.9, 136.6, 136.3, 132.6, 131.3, 129.3, 129.0, 127.4, 125.6, 37.2
7e	11.16(d, J=129.2 Hz, 2H), 7.85(d, J=7.5 Hz, 1H), 7.58(d, J=6.9 Hz, 2H), 7.41(t, J=7.4 Hz, 2H), 7.37—7.24(m, 3H), 7.09—6.95(m, 3H), 6.93—6.87(m, 1H), 4.40(s, 2H), 3.81(s, 3H)	160.9, 158.3, 157.6, 152.6, 146.1, 138.8, 136.4, 130.8, 129.8, 129.3, 127.4, 125.6, 124.8, 120.7, 111.6, 56.0, 33.6
7f	11.23(d, J=139.4 Hz, 2H), 7.87(d, J=6.5 Hz, 1H), 7.58(d, J=6.7 Hz, 2H), 7.37(dd, J=21.8, 6.6 Hz, 3H), 7.25(t, J=7.4 Hz, 1H), 7.00(t, J=10.5 Hz, 4H), 6.86(d, J=7.3 Hz, 1H), 4.45(s, 2H), 3.74(s, 3H)	160.9, 159.7, 157.9, 152.5, 146.2, 138.8, 138.7, 136.4, 130.1, 129.3, 129.3, 127.4, 125.6, 121.6, 115.1, 113.5, 55.5, 38.1
7g	11.22(d, J=128.7 Hz, 2H), 7.86(d, J=7.7 Hz, 1H), 7.57(d, J=7.4 Hz, 1H), 7.47—7.37(m, 2H), 7.32(t, J=8.4 Hz, 3H), 7.08—6.96(m, 2H), 6.89(dd, J=7.9, 4.2 Hz, 3H), 4.38(s, 2H), 3.73(s, 3H).	160.8, 159.1, 156.1, 152.5, 146.2, 138.7, 136.4, 130.8, 129.4, 127.4, 125.6, 114.4, 55.5, 37.8
7h	11.21(d, J=136.7 Hz, 2H), 7.86(d, J=6.9 Hz, 1H), 7.56(d, J=7.4 Hz, 2H), 7.39(t, J=7.4 Hz, 2H), 7.31(dd, J=9.8, 7.4 Hz, 2H), 7.22—7.10(m, 3H), 7.06—6.94(m, 2H), 4.47(s, 2H), 2.37(s, 3H)	160.9, 157.7, 152.6, 146.1, 138.8, 137.2, 136.4, 134.6, 129.4, 129.3, 128.4, 127.4, 126.5, 125.6, 36.7, 19.2
7i	11.20(d, J=128.1 Hz, 2H), 7.86(d, J=7.4 Hz, 1H), 7.57(d, J=7.2 Hz, 2H), 7.41(t, J=7.4 Hz, 2H), 7.33(t, J=7.3 Hz, 1H), 7.25—7.18(m, 3H), 7.12—7.05(m, 1H), 7.04—6.95(m, 2H), 4.44(s, 2H), 2.28(s, 3H)	160.8, 158.0, 152.6, 146.1, 138.8, 138.2, 137.0, 136.3, 130.1, 129.4, 129.3, 128.9, 128.7, 127.4, 126.6, 125.6, 38.1, 21.4
7j	11.17(d, J=134.6 Hz, 2H), 7.85(d, J=7.4 Hz, 1H), 7.56(d, J=7.1 Hz, 2H), 7.40(t, J=7.2 Hz, 2H), 7.31(dd, J=20.4, 7.4 Hz, 3H), 7.13(d, J=7.5 Hz, 2H), 7.09—6.93(m, 2H), 4.42(s, 2H), 2.27(s, 3H)	160.9, 157.7, 152.6, 146.1, 130.9, 130.4, 129.3, 128.4, 127.4, 126.5, 125.6, 36.7, 19.2
7k	11.22(d, J=107.8 Hz, 2H), 7.85(d, J=7.3 Hz, 1H), 7.56(d, J=7.3 Hz, 2H), 7.45(td, J=7.7, 1.6 Hz, 1H), 7.39(t, J=7.5 Hz, 2H), 7.34(dt, J=5.2, 2.0 Hz, 2H), 7.24—7.12(m, 2H), 7.06—6.95(m, 2H), 4.47(s, 2H)	160.9, 161.2, 157.0, 152.6, 146.2, 138.9, 136.3, 131.8, 130.4, 129.3, 127.4, 125.6, 125.0, 124.3, 116.1, 115.9, 32.0
7l	11.20(d, J=138.6 Hz, 2H), 7.87(d, J=7.5 Hz, 1H), 7.58(d, J=7.5 Hz, 2H), 7.50—7.44(m, 2H), 7.41(t, J=7.5 Hz, 2H), 7.35(d, J=7.2 Hz, 1H), 7.17(t, J=8.8 Hz, 2H), 7.08—6.95(m, 2H), 4.48(s, 2H)	163.2, 160.8, 157.6, 152.6, 146.1, 138.8, 136.3, 133.6, 131.5, 129.3, 127.4, 125.6, 115.9, 115.7, 37.3
7m	11.22(d, J=108.4 Hz, 2H), 7.86(dd, J=4.5, 3.6 Hz, 2H), 7.70—7.61(m, 2H), 7.57(d, J=7.3 Hz, 2H), 7.50(td, J=7.5, 1.4 Hz, 1H), 7.41(t, J=7.4 Hz, 2H), 7.34(d, J=7.2 Hz, 1H), 7.10—6.95(m, 2H), 4.61(s, 2H)	161.5, 156.2, 152.5, 146.2, 140.9, 138.9, 136.3, 133.8, 131.0, 129.3, 129.0, 127.4, 125.6, 117.7, 112.3, 36.7
7n	11.23(d, J=113.3 Hz, 2H), 7.86(d, J=8.0 Hz, 1H), 7.66(d, J=2.1 Hz, 1H), 7.57(d, J=7.3 Hz, 2H), 7.52(d, J=8.3 Hz, 1H), 7.44—7.37(m, 3H), 7.35(d, J=7.2 Hz, 1H), 7.08—6.95(m, 2H), 4.52(s, 2H)	161.3, 156.7, 152.6, 146.1, 138.9, 136.3, 134.8, 134.1, 133.7, 133.1, 129.5, 129.3, 128.0, 127.4, 125.6, 35.7
7o	11.21(d, J=147.4 Hz, 2H), 7.87(d, J=7.3 Hz, 1H), 7.58(d, J=7.4 Hz, 2H), 7.42(dt, J=14.7, 7.3 Hz, 2H), 7.38—7.23(m, 1H), 7.18—6.93(m, 2H), 2.71(s, 3H)	160.1, 158.6, 152.6, 146.0, 138.8, 136.4, 129.4, 129.3 127.4, 125.6, 16.4
7p	11.18(d, J=144.3 Hz, 2H), 7.86(d, J=7.6 Hz, 1H), 7.58(d, J=7.3 Hz, 2H), 7.41(t, J=7.4 Hz, 2H), 7.34(d, J=7.2 Hz, 1H), 7.09—6.95(m, 2H), 3.21(q, J=7.3 Hz, 2H), 1.35(t, J=7.3 Hz, 3H)	160.4, 158.4, 152.6, 146.0, 138.8, 136.4, 129.3, 127.4, 125.6, 28.5, 15.3
7q	11.20(d, J=148.3 Hz, 2H), 7.87(d, J=7.4 Hz, 1H), 7.58(d, J=7.7 Hz, 2H), 7.41(t, J=7.5 Hz, 2H), 7.34(d, J=7.3 Hz, 1H), 7.08—6.95(m, 2H), 3.18(t, J=7.1 Hz, 2H), 1.78—1.65(m, 2H), 0.99(t, J=7.3 Hz, 3H)	160.5, 158.6, 152.6, 146.1, 138.8, 136.5, 129.3, 127.4, 125.6, 36.0, 22.9, 13.4
7r	11.16(d, J=141.1 Hz, 2H), 7.85(d, J=7.7 Hz, 1H), 7.57(d, J=7.3 Hz, 2H), 7.42—7.39(m, 2H), 7.34(d, J=7.3 Hz, 1H), 7.08—6.96(m, 2H), 3.20(t, J=7.3 Hz, 2H), 1.67(dt, J=14.8, 7.4 Hz, 2H), 1.41(dq, J=14.6, 7.3 Hz, 2H), 0.90(t, J=7.4 Hz, 3H)	160.4, 158.7, 152.5, 146.1, 138.8, 136.4, 129.4, 127.4, 15.8, 33.8, 31.5, 21.6, 13.9
7s	11.20(d, J=145.6 Hz, 2H), 7.86(d, J=7.5 Hz, 1H), 7.58(d, J=7.2 Hz, 2H), 7.44—7.38(m, 3H), 7.08—6.96(m, 2H), 3.19(t, J=7.3 Hz, 2H), 1.74—1.63(m, 2H), 1.41—1.25(m, 4H), 0.87(t, J=7.2 Hz, 3H)	160.4, 158.7, 152.6, 146.1, 138.8, 129.3, 128.0, 127.4, 125.7, 125.6, 34.0, 30.6, 29.1, 22.1, 14.3

Compd.	Inhibition rate(%)
	X. oryzae		R. solanacearum		X. citri
	200 μg/mL	100 μg/mL	200 μg/mL	100 μg/mL	200 μg/mL	100 μg/mL
7a	81.02±1.15	72.38±0.35	90.78±0.47	61.56±0.38	61.72±2.45	36.35±0.32
7b	88.34±0.65	67.62±1.36	71.35±4.43	57.32±0.58	46.26±1.25	28.11±2.23
7c	72.13±1.25	47.04±1.21	58.63±1.19	31.25±1.28	58.47±0.57	39.04±0.92
7d	81.56±0.11	59.92±0.45	66.27±0.66	51.33±0.58	41.35±6.34	19.06±0.35
7e	90.00±0.23	82.11±1.32	91.92±1.03	78.83±1.24	89.62±2.15	72.37±7.14
7f	74.56±0.12	43.22±0.72	69.33±1.11	56.46±0.26	66.25±1.02	34.32±0.15
7g	96.00±0.33	73.11±0.26	93.22±0.66	88.17±0.15	75.11±0.24	41.31±0.44
7h	92.12±0.15	80.05±0.65	88.13±1.15	62.05±0.45	79.63±0.65	58.59±6.42
7i	100.03±0.24	100.17±1.44	91.03±8.24	79.82±4.06	87.25±6.44	66.93±1.43
7j	100.82±0.75	100.08±1.02	100.18±5.45	100.25±8.15	100.06±8.25	100.32±4.36
7k	100.02±1.16	100.15±1.21	100.34±2.83	100.01±6.54	100.25±1.93	100.17±8.04
7l	54.13±0.61	39.57±2.35	81.03±8.20	57.24±0.26	100.02±2.92	100.28±3.15
7m	62.78±0.72	39.52±1.22	82.93±4.21	64.82±5.42	66.46±9.01	47.82±4.33
7n	100.33±0.43	100.01±1.15	100.32±0.14	100.35±5.00	62.39±6.34	35.52±0.25
7o	71.22±0.15	42.38±0.55	60.88±0.37	31.66±1.38	62.52±1.45	31.35±0.22
7p	56.04±1.25	39.88±0.75	100.09±4.34	100.62±4.13	59.77±2.36	38.36±9.23
7q	67.26±0.55	59.65±2.42	100.26±5.82	100.35±6.74	100.05±3.11	100.14±2.17
7r	100.06±1.66	100.27±1.03	100.02±0.32	100.52±2.11	63.22±0.23	39.37±0.11
7s	61.11±0.34	42.66±2.16	100.61±1.23	100.86±8.07	67.42±0.14	48.73±8.14
Bismerthiazol^b	74.25±0.45	53.11±0.65	100.26±1.17	100.02±4.53	70.22±6.23	48.85±7.42
Thiodiazole-copper^b	70.17±1.35	41.56 ±1.01	55.63±1.20	41.32±5.39	63.51±8.15	44.27±3.46

Compd.	X. oryzae			R. solanacearu			X. citri
Compd.	EC₅₀/ (μg·mL^-1)	Regression equation	r	EC₅₀/ (μg·mL^-1)	Regression equation	r	EC₅₀/ (μg·mL^-1)	Regression equation	r
7e	38.02±2.15	y=1.7584x+2.2116	0.97	47.86±0.64	y=2.1183x+1.4312	0.97	67.20±2.24	y=1.7527x+1.8076	0.98
7g	36.88±0.29	y=2.0126x+1.8664	0.95	63.09±0.45	y=1.7527x+1.8076	0.96	—	—	—
7h	41.30±2.51	y=1.8947x+1.9382	0.98	—	—	—	—	—	—
7i	63.09±1.71	y=2.3573x+0.7284	0.96	—	—	—	—	—	—
7j	15.13±0.64	y=2.9303x+1.5332	0.96	30.90±1.03	y=1.9523x+2.0932	0.96	24.49±0.61	y=1.5289x+2.8762	0.99
7k	21.33±1.44	y=1.1424x+3.4811	0.97	24.54±0.53	y=1.5243x+2.8742	0.97	14.79±1.82	y=3.4379x+0.9771	0.98
7l	—	—	—	—	—	—	51.28±3.21	y=1.4098x+2.5822	0.99
7n	75.36±1.73	y=2.1535x+0.9522	0.96	86.09±2.13	y=1.4033x+2.2843	0.98	—	—	—
7p	—	—	—	37.15±2.35	y=1.2443x+3.0454	0.97	—	—	—
7q	—	—	—	23.98±1.41	y=2.8346x+1.0746	0.98	48.86±2.21	y=1.9589x+1.6904	0.97
7r	36.89±2.12	y=2.5243x+1.0433	0.97	39.81±2.82	y=1.3243x+2.8753	0.96	—	—	—
7s	—	—	—	56.75±0.61	y=1.8564x+1.7434	0.98	—	—	—
Bismert-	92.23±0.7	y=1.5038x+2.0433	0.98	58.88±1.01	y=1.2144x+2.8443	0.99	123.02±1.11	y=1.5143x+1.8278	0.99
hiazol

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含1,3,4-噻二唑结构的查尔酮缩氨基脲类化合物的合成及抗细菌活性

Synthesis and Antibacterial Activities Evaluation of Chalconesemicarbazone Derivatives Bearing 1,3,4-Thiadiazole Moiety†

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Synthesis and Antibacterial Activities Evaluation of Chalconesemicarbazone Derivatives Bearing 1,3,4-Thiadiazole Moiety^†