新型含5-芳基异噁唑结构的氰基丙烯酸酯类化合物的合成及生物活性

doi:10.7503/cjcu20160510

高等学校化学学报 ›› 2017, Vol. 38 ›› Issue (3): 421.doi: 10.7503/cjcu20160510

新型含5-芳基异噁唑结构的氰基丙烯酸酯类化合物的合成及生物活性

石玉军^1,²(), 方源¹, 李阳¹, 陈佳², 李刚³, 汪清民³, 戴红^2,³

1. 江苏科技大学环境与化学工程学院, 镇江 212003
2. 南通大学化学化工学院, 南通 226019
3. 南开大学元素有机化学国家重点实验室, 天津 300071

收稿日期:2016-07-18 出版日期:2017-03-10 发布日期:2017-02-23
作者简介:联系人简介: 石玉军, 男, 博士, 教授, 主要从事有机化学和农药化学研究. E-mail: yjshi2015@163.com
基金资助:
国家自然科学基金(批准号: 21372135)和元素有机化学国家重点实验室开放基金(批准号: 201412)资助.

Synthesis and Biological Activities of Novel Cyanoacrylate Derivatives Carrying 5-Arylisoxazole Group^†

SHI Yujun^1,^2,^*(), FANG Yuan¹, LI Yang¹, CHEN Jia², LI Gang³, WANG Qingmin³, DAI Hong^2,^3,^*

1. School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, China
2. College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, China
3. State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China

Received:2016-07-18 Online:2017-03-10 Published:2017-02-23
Contact: SHI Yujun,DAI Hong E-mail:yjshi2015@163.com
Supported by:
† Supported by the National Natural Science Foundation of China(No.21372135) and the Open Project Fund of State Key Laboratory of Elemento-organic Chemistry, China(No.201412).

摘要/Abstract

摘要：

通过5-取代苯基异噁唑-3-甲基胺与2-氰基-3,3-二甲硫基丙烯酸取代酯的缩合反应, 合成了一系列含5-取代苯基异噁唑环结构的氰基丙烯酸酯类衍生物, 并采用核磁共振波谱和元素分析对化合物的结构进行了表征. 初步的生物活性测试结果表明, 部分化合物显示出较好的除草活性, 在1500 g/ha剂量下, 化合物7h, 7i和7m对芥菜的茎叶处理抑制率分别为90%, 40%和100%; 化合物7m和7n对繁缕的茎叶处理抑制率分别为100%和80%; 化合物7m和7n对小藜的茎叶处理抑制率分别为100%和85%. 此外, 化合物7b和7c还表现出良好的抗肿瘤活性, 其对HepG2细胞的IC₅₀值分别为3.2和10.1 μmol/L.

关键词: 异噁唑, 氰基丙烯酸酯, 生物活性

Abstract:

In order to find novel cyanoacrylate derivatives with potent biological activities, fourteen new cyanoacrylates bearing a 5-arylisoxazole moiety were synthesized by multistep synthetic procedures with two key intermediates 5 and 6. The intermediate 5 was synthesized from methyl 5-arylisoxazolyl-3-carboxylate via reduction, chlorination, condensation, and hydrazine cleavage. The structures of target compounds 7 were confirmed by ¹H NMR,¹³C NMR and elemental analysis. The bioassay data showed that some target compounds exhibited good herbicidal activities at the dosage of 1500 g/ha. In postemergence treatment, compounds 7h, 7i, and 7m had 90%, 40%, and 100% herbicidal activity against Brassica juncea at 1500 g/ha, compounds 7m and 7n showed 100% and 80% herbicidal activity against Stellaria media at 1500 g/ha, compounds 7m and 7n displayed 100% and 85% inhibitory rates against Chenopodium serotinum L. at 1500 g/ha. In addition, some of the title compounds had satisfactory anti-tumor activities. Compounds 7b and 7c showed wonderful inhibitory activities against HepG2 cells with the IC₅₀values of 3.2 and 10.1 μmol/L, respectively.

Key words: Isoxazole, Cyanoacrylate, Biological activity

中图分类号:

O626

TrendMD:

石玉军, 方源, 李阳, 陈佳, 李刚, 汪清民, 戴红. 新型含5-芳基异噁唑结构的氰基丙烯酸酯类化合物的合成及生物活性. 高等学校化学学报, 2017, 38(3): 421.

SHI Yujun, FANG Yuan, LI Yang, CHEN Jia, LI Gang, WANG Qingmin, DAI Hong. Synthesis and Biological Activities of Novel Cyanoacrylate Derivatives Carrying 5-Arylisoxazole Group^†. Chem. J. Chinese Universities, 2017, 38(3): 421.

图/表 8

参考文献 21

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Compd.	m. p./℃	Compd.	m. p./℃	Compd.	m. p./℃
1a	152—153	3c	56—57	6b	154—156
1b	149—150	4a	156—158	6c	67—69
1c	150—151	4b	157—158	6d	33—34
2a	70—71	4c	155—157	6e	109—110
2b	92—93	5a	55—56	6f	66—67
2c	68—69	5b	55—57	6g	71—72
3a	58—59	5c	54—55	6h	33—35
3b	59—60	6a	69—70

Compd.	m. p./℃	Compd.	m. p./℃	Compd.	m. p./℃
1a	152—153	3c	56—57	6b	154—156
1b	149—150	4a	156—158	6c	67—69
1c	150—151	4b	157—158	6d	33—34
2a	70—71	4c	155—157	6e	109—110
2b	92—93	5a	55—56	6f	66—67
2c	68—69	5b	55—57	6g	71—72
3a	58—59	5c	54—55	6h	33—35
3b	59—60	6a	69—70

Compd.	¹H NMR(CDCl₃, 400 MHz), δ
1a	7.80—7.82(m, 2H, ArH), 7.17—7.21(m, 2H, ArH), 6.89(s, 1H, Isoxazole H), 4.01(s, 3H, OCH₃)
1b	7.75(d, J=8.0 Hz, 2H, ArH), 7.47(d, J=8.0 Hz, 2H, ArH), 6.83(s, 1H, Isoxazole H), 4.01(s, 3H, OCH₃)
1c	7.57—7.67(m, 2H, ArH), 7.30—7.34(m, 1H, ArH), 6.92(s, 1H, Isoxazole H), 4.02(s, 3H, OCH₃)
2a	7.71—7.73(m, 2H, ArH), 7.11—7.15(m, 2H, ArH), 6.53(s, 1H, Isoxazole H), 4.79(s, 2H, CH₂)
2b	7.66(d, J=8.4 Hz, 2H, ArH), 7.47(d, J=8.0 Hz, 2H, ArH), 6.57(s, 1H, Isoxazole H), 4.80(s, 2H, CH₂), 3.13(s, 1H, OH)
2c	7.57—7.61(m, 1H, ArH), 7.51(s, 1H, ArH), 7.24—7.30(m, 1H, ArH), 6.57(s, 1H, Isoxazole H), 4.81(s, 2H, CH₂), 2.21(s, 1H, OH)
3a	7.71(d, J=8.0 Hz, 2H, ArH), 7.45(d, J=8.0 Hz, 2H, ArH), 6.63(s, 1H, Isoxazole H), 4.64(s, 2H, CH₂)
3b	7.66(d, J=8.4 Hz, 2H, ArH), 7.40(d, J=8.0 Hz, 2H, ArH), 6.62(s, 1H, Isoxazole H), 4.64(s, 2H, CH₂)
3c	7.53—7.58(m, 2H, ArH), 7.25—7.32(m, 1H, ArH), 6.62(s, 1H, Isoxazole H), 4.64(s, 2H, CH₂)
4a	7.66—7.90(m, 6H, ArH), 7.41(d, J=8.0 Hz, 2H, ArH), 6.54(s, 1H, Isoxazole H), 5.00(s, 2H, CH₂)
4b	7.66—7.90(m, 6H, ArH), 7.41(d, J=6.8 Hz, 2H, ArH), 6.54(s, 1H, Isoxazole H), 5.00(s, 2H, CH₂)
4c	7.47—7.90(m, 6H, ArH), 7.21—7.27(m, 1H, ArH), 6.52(s, 1H, Isoxazole H), 5.00(s, 2H, CH₂)
5a	7.70(d, J=8.0 Hz, 2H, ArH), 7.43(d, J=8.0 Hz, 2H, ArH), 6.52(s, 1H, Isoxazole H), 3.99(s, 2H, CH₂), 2.13(s, 2H, NH₂)
5b	7.70(d, J=7.2 Hz, 2H, ArH), 7.44(d, J=7.2 Hz, 2H, ArH), 6.52(s, 1H, Isoxazole H), 3.99(s, 2H, CH₂), 1.85(s, 2H, NH₂)
5c	7.50—7.61(m, 2H, ArH), 7.23—7.29(m, 1H, ArH), 6.51(s, 1H, Isoxazole H),4.00(s, 2H, CH₂),1.90(s, 2H, NH₂)
6a	6.86—6.99(m, 4H, ArH), 4.54(s, 2H, CH₂), 4.21(s, 2H, CH₂), 2.76(s, 3H, SCH₃), 2.61(s, 3H, SCH₃)
6b	7.38(d,J=8.0 Hz, 2H, ArH), 6.81(d, J=8.0 Hz, 2H, ArH), 4.55(s, 2H, CH₂), 4.22(s, 2H, CH₂), 2.77(s, 3H, SCH₃), 2.61(s, 3H, SCH₃)
6c	7.36(s, 1H, ArH), 7.19(d, J=8.4 Hz, 1H, ArH), 6.94(d, J=8.8 Hz, 1H, ArH), 4.60(s, 2H, CH₂), 4.30(s, 2H, CH₂), 2.77(s, 3H, SCH₃), 2.61(s, 3H, SCH₃)
6d	4.36(s, 2H,CH₂), 3.72(s, 2H, CH₂), 3.58(q, J=7.2 Hz, 2H, CH₂), 2.76(s, 3H, SCH₃), 2.61(s, 3H, SCH₃), 1.21(t, J=7.2 Hz, 3H, CH₃)
6e	6.91—7.31(m, 5H, ArH), 4.56(s, 2H, CH₂), 4.25(s, 2H, CH₂), 2.75(s, 3H, SCH₃), 2.60(s, 3H, SCH₃)
6f	6.79—7.00(m, 3H, ArH), 4.59(s, 2H, CH₂), 4.35(s, 2H, CH₂), 2.77(s, 3H, SCH₃), 2.62(s, 3H, SCH₃)
6g	6.78—7.05(m, 3H, ArH), 4.55(s, 2H, CH₂), 4.30(s, 2H, CH₂), 2.77(s, 3H, SCH₃), 2.61(s, 3H, SCH₃)
6h	4.37(s, 2H, CH₂), 3.68(s, 2H, CH₂), 3.41(s, 3H, OCH₃), 2.76(s, 3H, SCH₃), 2.61(s, 3H, SCH₃)

Compd.	¹H NMR(CDCl₃, 400 MHz), δ
1a	7.80—7.82(m, 2H, ArH), 7.17—7.21(m, 2H, ArH), 6.89(s, 1H, Isoxazole H), 4.01(s, 3H, OCH₃)
1b	7.75(d, J=8.0 Hz, 2H, ArH), 7.47(d, J=8.0 Hz, 2H, ArH), 6.83(s, 1H, Isoxazole H), 4.01(s, 3H, OCH₃)
1c	7.57—7.67(m, 2H, ArH), 7.30—7.34(m, 1H, ArH), 6.92(s, 1H, Isoxazole H), 4.02(s, 3H, OCH₃)
2a	7.71—7.73(m, 2H, ArH), 7.11—7.15(m, 2H, ArH), 6.53(s, 1H, Isoxazole H), 4.79(s, 2H, CH₂)
2b	7.66(d, J=8.4 Hz, 2H, ArH), 7.47(d, J=8.0 Hz, 2H, ArH), 6.57(s, 1H, Isoxazole H), 4.80(s, 2H, CH₂), 3.13(s, 1H, OH)
2c	7.57—7.61(m, 1H, ArH), 7.51(s, 1H, ArH), 7.24—7.30(m, 1H, ArH), 6.57(s, 1H, Isoxazole H), 4.81(s, 2H, CH₂), 2.21(s, 1H, OH)
3a	7.71(d, J=8.0 Hz, 2H, ArH), 7.45(d, J=8.0 Hz, 2H, ArH), 6.63(s, 1H, Isoxazole H), 4.64(s, 2H, CH₂)
3b	7.66(d, J=8.4 Hz, 2H, ArH), 7.40(d, J=8.0 Hz, 2H, ArH), 6.62(s, 1H, Isoxazole H), 4.64(s, 2H, CH₂)
3c	7.53—7.58(m, 2H, ArH), 7.25—7.32(m, 1H, ArH), 6.62(s, 1H, Isoxazole H), 4.64(s, 2H, CH₂)
4a	7.66—7.90(m, 6H, ArH), 7.41(d, J=8.0 Hz, 2H, ArH), 6.54(s, 1H, Isoxazole H), 5.00(s, 2H, CH₂)
4b	7.66—7.90(m, 6H, ArH), 7.41(d, J=6.8 Hz, 2H, ArH), 6.54(s, 1H, Isoxazole H), 5.00(s, 2H, CH₂)
4c	7.47—7.90(m, 6H, ArH), 7.21—7.27(m, 1H, ArH), 6.52(s, 1H, Isoxazole H), 5.00(s, 2H, CH₂)
5a	7.70(d, J=8.0 Hz, 2H, ArH), 7.43(d, J=8.0 Hz, 2H, ArH), 6.52(s, 1H, Isoxazole H), 3.99(s, 2H, CH₂), 2.13(s, 2H, NH₂)
5b	7.70(d, J=7.2 Hz, 2H, ArH), 7.44(d, J=7.2 Hz, 2H, ArH), 6.52(s, 1H, Isoxazole H), 3.99(s, 2H, CH₂), 1.85(s, 2H, NH₂)
5c	7.50—7.61(m, 2H, ArH), 7.23—7.29(m, 1H, ArH), 6.51(s, 1H, Isoxazole H),4.00(s, 2H, CH₂),1.90(s, 2H, NH₂)
6a	6.86—6.99(m, 4H, ArH), 4.54(s, 2H, CH₂), 4.21(s, 2H, CH₂), 2.76(s, 3H, SCH₃), 2.61(s, 3H, SCH₃)
6b	7.38(d,J=8.0 Hz, 2H, ArH), 6.81(d, J=8.0 Hz, 2H, ArH), 4.55(s, 2H, CH₂), 4.22(s, 2H, CH₂), 2.77(s, 3H, SCH₃), 2.61(s, 3H, SCH₃)
6c	7.36(s, 1H, ArH), 7.19(d, J=8.4 Hz, 1H, ArH), 6.94(d, J=8.8 Hz, 1H, ArH), 4.60(s, 2H, CH₂), 4.30(s, 2H, CH₂), 2.77(s, 3H, SCH₃), 2.61(s, 3H, SCH₃)
6d	4.36(s, 2H,CH₂), 3.72(s, 2H, CH₂), 3.58(q, J=7.2 Hz, 2H, CH₂), 2.76(s, 3H, SCH₃), 2.61(s, 3H, SCH₃), 1.21(t, J=7.2 Hz, 3H, CH₃)
6e	6.91—7.31(m, 5H, ArH), 4.56(s, 2H, CH₂), 4.25(s, 2H, CH₂), 2.75(s, 3H, SCH₃), 2.60(s, 3H, SCH₃)
6f	6.79—7.00(m, 3H, ArH), 4.59(s, 2H, CH₂), 4.35(s, 2H, CH₂), 2.77(s, 3H, SCH₃), 2.62(s, 3H, SCH₃)
6g	6.78—7.05(m, 3H, ArH), 4.55(s, 2H, CH₂), 4.30(s, 2H, CH₂), 2.77(s, 3H, SCH₃), 2.61(s, 3H, SCH₃)
6h	4.37(s, 2H, CH₂), 3.68(s, 2H, CH₂), 3.41(s, 3H, OCH₃), 2.76(s, 3H, SCH₃), 2.61(s, 3H, SCH₃)

Compd.	Appearance	m. p. /℃	Yield(%)	Elemental analysis(%, calcd.)
Compd.	Appearance	m. p. /℃	Yield(%)	C	H	N
7a	Yellow solid	122—123	50	56.75(56.62)	3.78(3.92)	8.48(8.61)
7b	Yellow solid	>280	52	51.78(51.89)	3.73(3.60)	7.98(7.89)
7c	Yellow solid	198—199	53	52.73(52.88)	3.60(3.47)	7.95(8.04)
Compd.	Appearance	m. p. /℃	Yield(%)	Elemental analysis(%, calcd.)
Compd.	Appearance	m. p. /℃	Yield(%)	C	H	N
7d	Yellow solid	>280	51	56.40(56.28)	4.86(4.97)	10.25(10.36)
7e	Yellow solid	124—125	47	58.67(58.78)	4.41(4.29)	8.82(8.94)
7f	Yellow solid	130—131	52	54.89(54.77)	3.92(3.80)	8.18(8.33)
7g	Yellow solid	121—122	49	54.47(54.60)	3.72(3.59)	8.45(8.31)
7h	Yellow solid	130—131	51	54.73(54.60)	3.46(3.59)	8.17(8.31)
7i	Yellow solid	215—216	52	52.87(53.01)	4.57(4.45)	10.42(10.30)
7j	Yellow solid	94—96	48	54.21(54.09)	4.66(4.78)	9.83(9.96)
7k	Yellow solid	217—218	46	58.46(58.59)	4.18(4.06)	8.77(8.91)
7l	Yellow solid	222—223	45	54.47(54.60)	3.73(3.59)	8.43(8.31)
7m	Yellow solid	213—214	47	52.93(52.81)	4.08(4.19)	10.15(10.26)
7n	Yellow solid	>280	50	53.74(53.89)	4.66(4.52)	10.04(9.92)

新型含5-芳基异噁唑结构的氰基丙烯酸酯类化合物的合成及生物活性

Synthesis and Biological Activities of Novel Cyanoacrylate Derivatives Carrying 5-Arylisoxazole Group^†

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Compd.	¹H NMR(CDCl₃, 400 MHz), δ	¹³C NMR(CDCl₃, 100 MHz), δ
7a	10.43(s, 1H, NH), 7.75—7.78(m, 2H, ArH), 7.15—7.24(m, 4H, ArH), 6.86(d, J=9.2 Hz, 2H, ArH), 6.43(s, 1H, Isoxazole H), 4.91(d, J=6.0 Hz, 2H, CH₂), 4.51(t, J=5.2 Hz, 2H, CH₂), 4.21(t, J=5.2 Hz, 2H, CH₂), 2.73(s, 3H, SCH₃)	173.1, 170.4, 167.9, 165.3, 162.8, 160.3, 157.1, 129.4, 128.1, 128.0, 126.1, 123.3, 123.2, 117.6, 116.5, 116.3, 116.2, 97.7, 66.2, 63.0, 41.6, 18.4
7b	10.43(s, 1H, NH), 7.75—7.79(m, 2H, ArH), 7.37(d, J=9.2 Hz, 2H, ArH), 7.20—7.26(m, 2H, ArH), 6.81(d, J=9.2 Hz, 2H, ArH), 6.43(s, 1H, Isoxazole H), 4.91(d, J=6.0 Hz, 2H, CH₂), 4.52(t, J=5.2 Hz, 2H, CH₂), 4.21(t, J=5.2 Hz, 2H, CH₂), 2.73(s, 3H, SCH₃)	173.1, 170.4, 167.9, 162.8, 160.3, 157.6, 132.3, 128.1, 128.0, 123.2, 117.6, 116.7, 116.5, 116.3, 113.4, 97.7, 66.1, 63.0, 41.6, 18.5
7c	10.42(s, 1H, NH), 7.75—7.79(m, 2H, ArH), 7.34(d, J=2.4 Hz, 1H, ArH), 7.15—7.20(m, 3H, ArH), 6.95(d, J=8.8 Hz, 1H, ArH), 6.43(s, 1H, Isoxazole H), 4.92(d, J=5.6 Hz, 2H, CH₂), 4.56(t, J=5.2 Hz, 2H, CH₂), 4.29(t, J=5.2 Hz, 2H, CH₂), 2.73(s, 3H, SCH₃)	173.1, 170.4, 167.8, 165.3, 162.8, 160.3, 153.0, 130.1, 128.1, 128.0, 127.8, 126.6, 124.3, 123.2, 117.6, 116.5, 116.3, 115.5, 97.7, 67.7, 62.8, 41.6, 18.5
7d	10.44(s, 1H, NH), 7.75—7.79(m, 2H, ArH), 7.15—7.20(m, 2H, ArH), 6.43(s, 1H, Isoxazole H), 4.91(d, J=5.6 Hz, 2H, CH₂), 4.32(t, J=5.2 Hz, 2H, CH₂), 3.70(t, J=5.2 Hz, 2H, CH₂), 3.56(q, J=7.2 Hz, 2H, CH₂), 2.72(s, 3H, SCH₃), 1.21(t, J=7.2 Hz, 3H, CH₃)	172.7, 170.3, 168.0, 165.3, 162.8, 160.4, 128.1, 128.0, 123.3, 117.7, 116.5, 116.3, 97.7, 68.0, 66.9, 64.3, 41.5, 18.4, 15.2
7e	10.44(s, 1H, NH), 7.71(d, J=8.4 Hz, 2H, ArH), 7.46(d, J=8.4 Hz, 2H, ArH), 7.27—7.30(m, 2H, ArH), 6.92—6.96(m, 3H, ArH), 6.47(s, 1H, Isoxazole H), 4.91(d, J=6.0 Hz, 2H, CH₂), 4.53(t, J=5.2 Hz, 2H, CH₂), 4.24(t, J=5.2 Hz, 2H, CH₂), 2.73(s, 3H, SCH₃)	173.0, 170.2, 167.9, 160.4, 158.5, 136.8, 129.5, 129.4, 127.2, 125.3, 121.2, 117.6, 114.8, 98.2, 65.7, 63.2, 41.5, 18.4
7f	10.43(s, 1H, NH), 7.70(d, J=8.4 Hz, 2H, ArH), 7.45(d, J=8.4 Hz, 2H, ArH), 7.22(d, J=9.2 Hz, 2H, ArH), 6.85(d, J=8.8 Hz, 2H, ArH), 6.48(s, 1H, Isoxazole H), 4.91(d, J=6.0 Hz, 2H, CH₂), 4.51(t, J=5.2 Hz, 2H, CH₂), 4.20(t, J=5.2 Hz, 2H, CH₂), 2.73(s, 3H, SCH₃)	173.1, 170.2, 167.9, 160.3, 157.1, 136.9, 129.5, 129.4, 127.2, 126.1, 125.3, 117.6, 116.2, 98.2, 66.2, 63.1, 41.6, 18.4
7g	10.43(s, 1H, NH), 7.71(d, J=8.4 Hz, 2H, ArH), 7.45(d, J=8.4 Hz, 2H, ArH), 6.96—7.01(m, 1H, ArH), 6.76—6.83(m, 2H, ArH), 6.49(s, 1H, Isoxazole H), 4.92(d, J=6.0 Hz, 2H, CH₂), 4.55(t, J=4.8 Hz, 2H, CH₂), 4.33(t, J=5.2 Hz, 2H, CH₂), 2.73(s, 3H, SCH₃)	173.0, 170.2, 167.8, 160.4, 154.2, 151.8, 146.5, 146.4, 136.8, 129.4, 127.2, 125.3, 124.5, 124.4, 122.1, 117.6, 116.5, 116.3, 98.2, 67.6, 63.1, 41.5, 18.4
7h	10.43(s, 1H, NH), 7.71(d, J=8.8 Hz, 2H, ArH), 7.46(d, J=8.8 Hz, 2H, ArH), 7.00—7.06(m, 1H, ArH), 6.77—6.87(m, 2H, ArH), 6.48(s, 1H, Isoxazole H), 4.92(d, J=6.0 Hz, 2H, CH₂), 4.52(t, J=4.8 Hz, 2H, CH₂), 4.28(t, J=4.8 Hz, 2H, CH₂), 2.73(s, 3H, SCH₃)	173.0, 170.2, 167.9, 160.3, 158.7, 156.4, 154.6, 136.9, 129.5, 127.2, 125.3, 117.6, 116.1, 116.0, 115.8, 98.2, 66.6, 63.2, 41.5, 18.4
7i	10.44(s, 1H, NH), 7.71(d, J=8.4 Hz, 2H, ArH), 7.46(d, J=8.4 Hz, 2H, ArH), 6.47(s, 1H, Isoxazole H), 4.91(d, J=6.0 Hz, 2H, CH₂), 4.33(t, J=4.8 Hz, 2H, CH₂), 3.67(t, J=4.8 Hz, 2H, CH₂), 3.41(s, 3H, OCH₃), 2.73(s, 3H, SCH₃)	172.8, 170.1, 168.0, 160.4, 136.8, 129.5, 127.2, 125.3, 117.7, 98.2, 70.3, 64.1, 59.3, 41.5, 18.4
7j	10.44(s, 1H, NH), 7.71(d, J=8.8 Hz, 2H, ArH), 7.45(d, J=8.4 Hz, 2H, ArH), 6.48(s, 1H, Isoxazole H), 4.91(d, J=6.0 Hz, 2H, CH₂), 4.32(t, J=5.2 Hz, 2H, CH₂), 3.70(t, J=5.2 Hz, 2H, CH₂), 3.58(q, J=6.8 Hz, 2H, CH₂), 2.72(s, 3H, SCH₃), 1.21(t, J=7.2 Hz, 3H, CH₃)	172.7, 170.1, 168.0, 160.5, 136.8, 129.5, 127.2, 125.3, 117.7, 98.2, 68.1, 66.9, 64.3, 41.5, 18.4, 15.2
7k	10.44(s, 1H, NH), 7.58—7.63(m, 1H, ArH), 7.51—7.55(m, 1H, ArH), 7.27—7.32(m, 3H, ArH), 6.92—6.98(m, 3H, ArH), 6.46(s, 1H, Isoxazole H), 4.92(d, J = 6.0 Hz, 2H, CH₂), 4.54(t, J=5.2 Hz, 2H, CH₂), 4.24(t, J=5.2 Hz, 2H, CH₂), 2.73(s, 3H, SCH₃)	173.0, 169.1, 167.9, 160.5, 158.5, 129.5, 123.9, 123.8, 122.6, 122.5, 121.2, 118.5, 118.3, 117.6, 115.4, 115.2, 114.8, 98.5, 65.7, 63.2, 41.5, 18.5
7l	10.43(s, 1H, NH), 7.57—7.62(m, 1H, ArH), 7.51—7.55(m, 1H, ArH), 7.28—7.32(m, 1H, ArH), 7.23(d, J=8.8 Hz, 2H, ArH), 6.86(d, J=9.2 Hz, 2H, ArH), 6.46(s, 1H, Isoxazole H), 4.92(d, J=6.0 Hz, 2H, CH₂), 4.52(t, J=5.2 Hz, 2H, CH₂), 4.21(t, J=5.2 Hz, 2H, CH₂), 2.74(s, 3H, SCH₃)	173.1, 169.1, 167.9, 160.4, 157.1, 129.4, 123.9, 123.8, 122.6, 122.5, 118.5, 118.3, 117.6, 116.2, 115.4, 115.2, 98.5, 66.2, 63.2, 41.5, 18.4
7m	10.43(s, 1H, NH), 7.58—7.63(m, 1H, ArH), 7.51—7.55(m, 1H, ArH), 7.26—7.32(m, 1H, ArH), 6.46(s, 1H, Isoxazole H), 4.91(d, J=5.6 Hz, 2H, CH₂), 4.33(t, J=5.2 Hz, 2H, CH₂), 3.66(t, J=4.8 Hz, 2H, CH₂), 3.41(s, 3H, OCH₃), 2.73(s, 3H, SCH₃)	172.8, 169.1, 168.0, 160.6, 123.9, 123.8, 122.6, 122.5, 118.5, 117.7, 115.4, 115.2, 98.5, 70.3, 64.1, 59.3, 41.4, 18.4
7n	10.44(s, 1H, NH), 7.52—7.63(m, 2H, ArH), 7.26—7.32(m, 1H, ArH), 6.47(s, 1H, Isoxazole H), 4.92(d, J=5.6 Hz, 2H, CH₂), 4.32(t, J=5.2 Hz, 2H, CH₂), 3.70(t, J=5.2 Hz, 2H, CH₂), 3.58(q, J=7.2 Hz, 2H, CH₂), 2.73(s, 3H, SCH₃), 1.21(t, J=7.2 Hz, 3H, CH₃)	172.7, 169.1, 168.0, 160.6, 123.9, 123.8, 122.6, 122.5, 118.5, 118.3, 117.6, 115.4, 98.5, 68.0, 66.9, 64.3, 41.4, 18.4, 15.2

Compd.	Postemergence treatment
Compd.	Brassica juncea	Stellaria media	Chenopodium serotinum L.
7h	90	0	0
7i	40	0	0
7m	100	100	100
7n	20	80	85
NK-9717	100	100	100

Compd.	IC₅₀/(μmol·L^-1)		Compd.	IC₅₀/(μmol·L^-1)
Compd.	HepG2		SGC7901	HepG2	SGC7901
7a	>20	>20	7i	>20	>20
7b	3.2	>20	7j	>20	>20
7c	10.1	>20	7k	>20	>20
7d	>20	>20	7l	>20	>20
7e	>20	>20	7m	>20	>20
7f	>20	>20	7n	>20	>20
7g	>20	>20	Sorafenib	16.2	12.1
7h	>20	>20

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新型含5-芳基异噁唑结构的氰基丙烯酸酯类化合物的合成及生物活性

Synthesis and Biological Activities of Novel Cyanoacrylate Derivatives Carrying 5-Arylisoxazole Group†

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Synthesis and Biological Activities of Novel Cyanoacrylate Derivatives Carrying 5-Arylisoxazole Group^†