高等学校化学学报 ›› 2017, Vol. 38 ›› Issue (3): 421.doi: 10.7503/cjcu20160510
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
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: 基金资助:
SHI Yujun1,2,*(), FANG Yuan1, LI Yang1, CHEN Jia2, LI Gang3, WANG Qingmin3, DAI Hong2,3,*
Received:
2016-07-18
Online:
2017-03-10
Published:
2017-02-23
Contact:
SHI Yujun,DAI Hong
E-mail:yjshi2015@163.com
Supported by:
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.
中图分类号:
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.
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 |
Table 1 Melting point data of intermediate compounds 1—6
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) |
Table 2 1H NMR data of intermediate compounds 1—6
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.) | ||
---|---|---|---|---|---|---|
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.) | ||
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) |
Table 3 Appearance, melting points, yields and elemental analysis data of target compounds 7a—7n
Compd. | Appearance | m. p. /℃ | Yield(%) | Elemental analysis(%, calcd.) | ||
---|---|---|---|---|---|---|
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.) | ||
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) |
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 |
Table 4 1H NMR and 13C NMR data of target compounds 7a—7n
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 | ||
---|---|---|---|
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 |
Table 5 Herbicidal activities(%) of some title compounds 7(1500 g/ha)
Compd. | Postemergence treatment | ||
---|---|---|---|
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) | ||
---|---|---|---|---|---|
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 |
Table 6 Anti-tumor activities of title compounds 7a—7n
Compd. | IC50/(μmol·L-1) | Compd. | IC50/(μmol·L-1) | ||
---|---|---|---|---|---|
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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