CN107118185B - N-[(3-杂环基)丙烯酰基]苯基丙烯酰胺类衍生物及其应用 - Google Patents

N-[(3-杂环基)丙烯酰基]苯基丙烯酰胺类衍生物及其应用 Download PDF

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CN107118185B
CN107118185B CN201710487701.6A CN201710487701A CN107118185B CN 107118185 B CN107118185 B CN 107118185B CN 201710487701 A CN201710487701 A CN 201710487701A CN 107118185 B CN107118185 B CN 107118185B
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CN107118185A (zh
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唐孝荣
刘辉
高扬
严映坤
杨建�
曾义
李唯一
张燕
陈绍玲
郭玉娇
陶会敏
王瑶
李鑫松
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Jiangsu Guojiao New Materials Co ltd
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Abstract

本发明涉及酰胺类化合物及其制备方法和应用，具体涉及含杂环基团的N‑[(3‑杂环基)丙烯酰基]苯基丙烯酰胺类衍生物及其应用。本发明解决的技术问题是提供一种可作为抗氧化剂和农用杀虫剂使用的酰胺类化合物。该化合物的结构式如式Ⅰ所示。本发明采用生物活性基团拼接原理，将杂环化合物引入酰胺化合物中，发现了一些结构新颖、活性优异的活性化合物或活性先导化合物，从而为新型抗氧化剂及杀虫剂的创制奠定了较好的基础。

Description

N-[(3-杂环基)丙烯酰基]苯基丙烯酰胺类衍生物及其应用
技术领域
本发明涉及酰胺类化合物及其制备方法和应用，具体涉及N-[(3-杂环基)丙烯酰基]苯基丙烯酰胺类衍生物及其应用。
背景技术
抗氧化剂能有效地延缓或抑制许多物质，特别是糖、脂、蛋白质、核酸等生物大分子的氧化变质，在许多领域都有着十分广泛的应用：(1)在食品加工方面，抗氧化剂能抑制油脂氧化，防止其酸败，常作为食品抗氧化添加剂；(2)在生命科学和医学领域，抗氧化剂能清除体内自由基，减缓机体过氧化状态的形成，预防和治疗自由基引起的各种疾病，提高机体免疫能力，从而保护人体健康；(3)在化学工业领域，抗氧化剂作为化工产品的稳定性添加剂，提高产品的抗氧化性能，从而延长其使用寿命。由于抗氧化剂在工农业生产及日常生活中都发挥着不可替代的作用，因此，高效、经济、低毒的抗氧化剂的研究与开发具有十分重要的意义。
另一方面，农药特别是杀虫剂的长期大量使用不仅污染了环境、破坏了生态平衡，还导致了严重的“3R”(残留、抗性和害虫再猖獗)和“三致”(致癌、致畸形和致突变)问题。这些问题引起了人类广泛的关注，如何有效地解决这些问题是人类面临的一项长期而艰巨的任务。这样，在农药面临着巨大的挑战，而人类又离不开农药的情况下，寻找对有害生物高效、对非靶标生物安全、在环境中易降解且降解产物对人类健康和生态环境安全的“环境和谐农药”或“绿色农药”已经成了农药研究的热点和前沿。
酰胺类化合物具有广泛的生物活性，包括杀菌、抗氧化、植物生长调节等。因此，在过去几十年中，对其进行了广泛而深入的研究，发现了许多新型高效的化合物，而且还不断有结构新颖、作用方式独特、性能优异、对有害生物高效、对非靶标生物安全、在环境中易降解且降解产物对人类健康和生态环境安全的品种报道。
到目前为止，还未见有酰胺类化合物作为抗氧化剂和农用杀虫剂使用的报道。
发明内容
本发明解决的技术问题是提供一种可作为抗氧化剂和农用杀虫剂使用的酰胺类化合物。
本发明的N-[(3-杂环基)丙烯酰基]苯基丙烯酰胺类衍生物，其结构式如式Ⅰ所示：
其中，R1为R2为氢或卤素；R3为氢或卤素；X为O或S。
优选的，R1为
优选的，结构式如式Ⅰ-1或式Ⅰ-2所示：
本发明还提供本发明化合物在制备抗氧化剂中的用途。
本发明的化合物，具有优异的抗氧化性能，可用作抗氧化剂。
本发明还提供本发明化合物在杀灭农业害虫中的用途。
本发明的化合物，也可用作杀虫剂，对粘虫、朱砂叶螨、淡色库蚊等农业害虫具有较好的毒杀活性。因此，优选所述农业害虫为粘虫、朱砂叶螨或淡色库蚊。
本发明采用生物活性基团拼接原理，将杂环化合物引入酰胺化合物中，发现了一些结构新颖、活性优异的活性化合物或活性先导化合物，从而为新型抗氧化剂及杀虫剂的创制奠定了较好的基础。
具体实施方式
本发明提供结构式如式Ⅰ所示的化合物：
其中，R1为R2为氢或卤素；R3为氢或卤素；X为O或S。
优选的，R1为
在苯环上的位置可以为邻位、间位或者对位等，优选为间位或对位，即优选结构式如式Ⅰ-1或式Ⅰ-2所示：
以下是本发明优选的一些化合物。
本发明的化合物，可以采用常规的制备方法得到，其反应原理如下：
本发明的化合物，具有优异的抗氧化性能，可用作抗氧化剂。
本发明的化合物，也可用作杀虫剂，对粘虫、朱砂叶螨、淡色库蚊等农业害虫具有较好的毒杀活性。
下面结合实施例对本发明的具体实施方式做进一步的描述，并不因此将本发明限制在所述的实施例范围之中。
实施例1化合物1～6的合成
1、化合物1的合成方法
(1)将3-氨基苯乙酮(0.01mol)溶于无水乙醇(10mL)后，加入到50mL三颈瓶中，再将NaOH的乙醇溶液(10％，5mL)加入到该溶液。在搅拌和冰水浴的条件下，将糠醛(0.01mol)和无水乙醇(10mL)的混合物缓慢加入到上述溶液，控制反应温度保持在0-5℃，并通过薄层硅胶板(TLC)检测终点。反应完成后，向反应混合物中加入适量蒸馏水(有大量固体析出)，用10％HCl将溶液的pH值调节至约为7，将沉淀的固体过滤并用蒸馏水洗涤，得到的粗产品用无水乙醇重结晶，得到中间体。
(2)将自制的中间体(0.005mol)溶于二氯甲烷(10mL)，加入到50mL三颈瓶中，再将三乙胺(3mL)加入到该溶液中。在搅拌和冰水浴的条件下，将丙烯酰氯(0.015mol)和二氯甲烷(5mL)的混合液用恒压滴液漏斗慢慢滴入三颈瓶中，控制反应温度保持在0-5℃，并通过薄层硅胶板(TLC)检测终点。当反应完成后，依次用盐酸(10％)和氢氧化钠(10％)洗涤反应液，减压蒸馏除去溶剂(二氯甲烷)，得到粗产品，再用无水乙醇重结晶，即得到产品。
黄色粉末状固体；IR(KBr)νmax(cm-1):3440,3333,1694,1659,1582,1556,1484,1385,964,762,677；1H NMR(400MHz,DMSO-d6)δ(ppm):10.42(s,1H),8.34(s,1H),8.00(dd,J1＝1.2Hz,J2＝1.2Hz,1H),7.95(d,J＝1.2Hz,1H),7.79(d,J＝7.6Hz,1H),7.61(d,J＝15.2Hz,1H),7.54(t,J＝8.0Hz,1H),7.48(d,J＝15.2Hz,1H),7.13(d,J＝3.2Hz,1H),6.72(dd,J1＝1.6Hz,J2＝2.0Hz,1H),6.50–6.43(m,1H),6.34–6.29(m,1H),5.83–5.81(m,1H)；13C NMR(100MHz,DMSO-d6)δ(ppm):188.76(1C),163.89(1C),151.50(1C),146.82(1C),140.02(1C),138.49(1C),132.11(1C),131.10(1C),129.93(1C),127.89(1C),124.09(1C),123.85(1C),119.20(1C),118.87(1C),117.95(1C),113.67(1C)；HRMS(ESI)m/z:Calcd forC16H14NO3[M+H]+:268.0968,Found:268.0966.
2、化合物2的合成方法
(1)将3-氨基苯乙酮(0.01mol)溶于无水乙醇(10mL)后，加入到50mL三颈瓶中，再将NaOH的乙醇溶液(10％，5mL)加入到该溶液。在搅拌和冰水浴的条件下，将噻吩-2-甲醛(0.01mol)和无水乙醇(10mL)的混合物缓慢加入到上述溶液，控制反应温度保持在0-5℃，并通过薄层硅胶板(TLC)检测终点。反应完成后，向反应混合物中加入适量蒸馏水(有大量固体析出)，用10％HCl将溶液的pH值调节至约为7，将沉淀的固体过滤并用蒸馏水洗涤，得到的粗产品用无水乙醇重结晶，得到中间体。
(2)将自制的中间体(0.005mol)溶于二氯甲烷(10mL)，加入到50mL三颈瓶中，再将三乙胺(3mL)加入到该溶液中。在搅拌和冰水浴的条件下，将丙烯酰氯(0.015mol)和二氯甲烷(5mL)的混合液用恒压滴液漏斗慢慢滴入三颈瓶中，控制反应温度保持在0-5℃，并通过薄层硅胶板(TLC)检测终点。当反应完成后，依次用盐酸(10％)和氢氧化钠(10％)洗涤反应液，减压蒸馏除去溶剂(二氯甲烷)，得到粗产品，再用无水乙醇重结晶，即得到产品。
淡黄色粉末状固体；IR(KBr)νmax(cm-1):3434,3302,1667,1586,1552,1487,1384,972,795,710；1H NMR(400MHz,DMSO-d6)δ(ppm):10.41(s,1H),8.29(t,J＝2.0Hz,1H),8.02(dd,J1＝1.2Hz,J2＝1.6Hz,1H),7.95(d,J＝15.6Hz,1H),7.82(t,J＝9.6Hz,2H),7.71(d,J＝3.6Hz,1H),7.54(t,J＝8.0Hz,1H),7.49(d,J＝15.2Hz,1H),7.22(dd,J1＝3.6Hz,J2＝3.6Hz,1H),6.50–6.43(m,1H),6.34–6.29(m,1H),5.83–5.80(m,1H)；13C NMR(100MHz,DMSO-d6)δ(ppm):188.90(1C),163.90(1C),140.14(1C),140.00(1C),138.53(1C),137.45(1C),133.60(1C),132.15(1C),130.95(1C),129.83(1C),129.24(1C),127.80(1C),124.18(1C),124.03(1C),120.69(1C),119.24(1C)；HRMS(ESI)m/z:Calcd for C16H14NO2S[M+H]+:284.0740,Found:284.0733.
3、化合物3的合成方法
(1)将4-氨基苯乙酮(0.01mol)溶于无水乙醇(10mL)后，加入到50mL三颈瓶中，再将NaOH的乙醇溶液(10％，5mL)加入到该溶液。在搅拌和冰水浴的条件下，将糠醛(0.01mol)和无水乙醇(10mL)的混合物缓慢加入到上述溶液，控制反应温度保持在0-5℃，并通过薄层硅胶板(TLC)检测终点。反应完成后，向反应混合物中加入适量蒸馏水(有大量固体析出)，用10％HCl将溶液的pH值调节至约为7，将沉淀的固体过滤并用蒸馏水洗涤，得到的粗产品用无水乙醇重结晶，得到中间体。
(2)将自制的中间体(0.005mol)溶于二氯甲烷(10mL)，加入到50mL三颈瓶中，再将三乙胺(3mL)加入到该溶液中。在搅拌和冰水浴的条件下，将丙烯酰氯(0.015mol)和二氯甲烷(5mL)的混合液用恒压滴液漏斗慢慢滴入三颈瓶中，控制反应温度保持在0-5℃，并通过薄层硅胶板(TLC)检测终点。当反应完成后，依次用盐酸(10％)和氢氧化钠(10％)洗涤反应液，减压蒸馏除去溶剂(二氯甲烷)，得到粗产品，再用无水乙醇重结晶，即得到产品。
深黄色粉末状固体；IR(KBr)νmax(cm-1):3438,3274,1667,1599,1530,1474,1385,976,816；1H NMR(400MHz,DMSO-d6)δ(ppm):10.54(s,1H),8.10(d,J＝8.8Hz,2H),7.91(s,1H),7.87(d,J＝8.8Hz,2H),7.57(s,2H),7.09(d,J＝3.2Hz,1H),6.69(dd,J1＝1.6Hz,J2＝1.6Hz,1H),6.52–6.46(m,1H),6.35–6.31(m,1H),5.84–5.81(m,1H)；13C NMR(100MHz,DMSO-d6)δ(ppm):187.43(1C),164.07(1C),151.70(1C),146.51(1C),143.86(1C),132.91(1C),131.99(1C),130.44(1C),130.16(2C),128.34(1C),119.31(2C),119.09(1C),117.24(1C),113.55(1C)；HRMS(ESI)m/z:Calcd for C16H14NO3[M+H]+:268.0968,Found:268.0965.
4、化合物4的合成方法
(1)将4-氨基苯乙酮(0.01mol)溶于无水乙醇(10mL)后，加入到50mL三颈瓶中，再将NaOH的乙醇溶液(10％，5mL)加入到该溶液。在搅拌和冰水浴的条件下，将噻吩-2-甲醛(0.01mol)和无水乙醇(10mL)的混合物缓慢加入到上述溶液，控制反应温度保持在0-5℃，并通过薄层硅胶板(TLC)检测终点。反应完成后，向反应混合物中加入适量蒸馏水(有大量固体析出)，用10％HCl将溶液的pH值调节至约为7，将沉淀的固体过滤并用蒸馏水洗涤，得到的粗产品用无水乙醇重结晶，得到中间体。
(2)将自制的中间体(0.005mol)溶于二氯甲烷(10mL)，加入到50mL三颈瓶中，再将三乙胺(3mL)加入到该溶液中。在搅拌和冰水浴的条件下，将丙烯酰氯(0.015mol)和二氯甲烷(5mL)的混合液用恒压滴液漏斗慢慢滴入三颈瓶中，控制反应温度保持在0-5℃，并通过薄层硅胶板(TLC)检测终点。当反应完成后，依次用盐酸(10％)和氢氧化钠(10％)洗涤反应液，减压蒸馏除去溶剂(二氯甲烷)，得到粗产品，再用无水乙醇重结晶，即得到产品。
黄色粉末状固体；IR(KBr)νmax(cm-1):3433,1668,1638,1595,1530,1384,974,820；1H NMR(400MHz,DMSO-d6)δ(ppm):10.54(s,1H),8.13(d,J＝8.4Hz,2H),7.91(d,J＝15.2Hz,1H),7.86(d,J＝8.8Hz,2H),7.80(d,J＝4.8Hz,1H),7.70(d,J＝3.2Hz,1H),7.59(d,J＝15.2Hz,1H),7.21(dd,J1＝4.0Hz,J2＝3.6Hz,1H),6.52–6.46(m,1H),6.35–6.31(m,1H),5.85–5.82(m,1H)；13C NMR(100MHz,DMSO-d6)δ(ppm):187.45(1C),164.06(1C),143.87(1C),140.31(1C),136.68(1C),133.19(1C),132.88(1C),131.99(1C),130.76(1C),130.26(2C),129.17(1C),128.38(1C),120.68(1C),119.26(2C)；HRMS(ESI)m/z:Calcd forC16H14NO2S[M+H]+:284.0740,Found:284.0736.
5、化合物5的合成方法
(1)将4-氨基苯乙酮(0.01mol)溶于无水乙醇(10mL)后，加入到50mL三颈瓶中，再将NaOH的乙醇溶液(10％，5mL)加入到该溶液。在搅拌和冰水浴的条件下，将3-吡啶甲醛(0.01mol)和无水乙醇(10mL)的混合物缓慢加入到上述溶液，控制反应温度保持在0-5℃，并通过薄层硅胶板(TLC)检测终点。反应完成后，向反应混合物中加入适量蒸馏水(有大量固体析出)，用10％HCl将溶液的pH值调节至约为7，将沉淀的固体过滤并用蒸馏水洗涤，得到的粗产品用无水乙醇重结晶，得到中间体。
(2)将自制的中间体(0.005mol)溶于二氯甲烷(10mL)，加入到50mL三颈瓶中，再将三乙胺(3mL)加入到该溶液中。在搅拌和冰水浴的条件下，将丙烯酰氯(0.015mol)和二氯甲烷(5mL)的混合液用恒压滴液漏斗慢慢滴入三颈瓶中，控制反应温度保持在0-5℃，并通过薄层硅胶板(TLC)检测终点。当反应完成后，依次用盐酸(10％)和氢氧化钠(10％)洗涤反应液，减压蒸馏除去溶剂(二氯甲烷)，得到粗产品，再用无水乙醇重结晶，即得到产品。
黄色晶体；IR(KBr)νmax(cm-1):3434,1682,1659,1608,1597,1535,1478,1384,985,838；1H NMR(400MHz,DMSO-d6)δ(ppm):10.56(s,1H),9.04(d,J＝2.0Hz,1H),8.63(dd,J1＝1.6Hz,J2＝1.6Hz,1H),8.39–8.36(m,1H),8.22(d,J＝8.8Hz,2H),8.11(d,J＝15.6Hz,1H),7.88(d,J＝8.8Hz,2H),7.77(d,J＝15.6Hz,1H),7.51(dd,J1＝4.8Hz,J2＝4.8Hz,1H),6.52–6.46(m,1H),6.36–6.31(m,1H),5.86–5.83(m,1H)；13C NMR(100MHz,DMSO-d6)δ(ppm):187.74(1C),164.10(1C),151.39(1C),150.81(1C),144.09(1C),140.45(1C),135.54(1C),132.72(1C),131.97(1C),131.08(1C),130.55(2C),128.45(1C),124.38(1C),124.26(1C),119.24(2C)；HRMS(ESI)m/z:Calcd for C17H15N2O2[M+H]+:279.1128,Found:279.1121.
6、化合物6的合成方法
(1)将4-氨基苯乙酮(0.01mol)溶于无水乙醇(10mL)后，加入到50mL三颈瓶中，再将NaOH的乙醇溶液(10％，5mL)加入到该溶液。在搅拌和冰水浴的条件下，将2-呋喃基丙烯醛(0.01mol)和无水乙醇(10mL)的混合物缓慢加入到上述溶液，控制反应温度保持在0-5℃，并通过薄层硅胶板(TLC)检测终点。反应完成后，向反应混合物中加入适量蒸馏水(有大量固体析出)，用10％HCl将溶液的pH值调节至约为7，将沉淀的固体过滤并用蒸馏水洗涤，得到的粗产品用无水乙醇重结晶，得到中间体。
(2)将自制的中间体(0.005mol)溶于二氯甲烷(10mL)，加入到50mL三颈瓶中，再将三乙胺(3mL)加入到该溶液中。在搅拌和冰水浴的条件下，将丙烯酰氯(0.015mol)和二氯甲烷(5mL)的混合液用恒压滴液漏斗慢慢滴入三颈瓶中，控制反应温度保持在0-5℃，并通过薄层硅胶板(TLC)检测终点。当反应完成后，依次用盐酸(10％)和氢氧化钠(10％)洗涤反应液，减压蒸馏除去溶剂(二氯甲烷)，得到粗产品，再用无水乙醇重结晶，即得到产品。
棕色粉末状固体；IR(KBr)νmax(cm-1):3434,1649,1595,1527,1470,1384,993,818；1H NMR(400MHz,DMSO-d6)δ(ppm):10.53(s,1H),8.05(d,J＝8.4Hz,2H),7.86(s,1H),7.83(d,J＝8.0Hz,2H),7.54–7.37(m,2H),7.09(d,J＝15.6Hz,1H),7.00–6.94(m,1H),6.74(d,J＝3.2Hz,1H),6.62(dd,J1＝1.6Hz,J2＝2.0Hz,1H),6.52–6.45(m,1H),6.35–6.30(m,1H),5.85–5.82(m,1H)；13C NMR(100MHz,DMSO-d6)δ(ppm):187.81(1C),164.05(1C),152.45(1C),145.28(1C),143.83(1C),143.74(1C),133.12(1C),131.99(1C),130.04(2C),128.67(1C),128.37(1C),125.61(2C),119.25(2C),113.25(1C),113.16(1C)；HRMS(ESI)m/z:Calcd for C18H16NO3[M+H]+:294.1125,Found:294.1123.
试验例1本发明化合物杀虫活性的测定
1、供试害虫
粘虫3龄幼虫，朱砂叶螨成螨，淡色库蚊3龄幼虫，它们均为室内常年累代饲养的敏感品系。
2、粘虫的测定方法
将待测样品溶解于二甲亚砜并用0.1％吐温-80水溶液稀释成一定的浓度，以不加待测样品的相应溶液为阴性对照。将玉米叶片剪成2×4cm的小段，在待测溶液中浸5s后拿开，沥干后放入底部铺有滤纸的培养皿(6cm)中，接入15头3龄幼虫，再将其放置在温度为22～24℃，相对湿度为60％，光照时间为14:10h的实验室中继续饲养，24h后记录死亡情况，每一实验重复三次，并用下列公式计算校正死亡率：
3、朱砂叶螨的测定方法
将待测样品溶解于二甲亚砜并用0.1％吐温-80水溶液稀释成一定的浓度，以不加待测样品的相应溶液为阴性对照。采集虫口密度大的菜豆叶，仔细挑选使健康的成螨(30～50头)留在叶面上，将带虫的菜豆叶浸入待测溶液5s后拿开，沥干后放入底部铺有滤纸的培养皿(6cm)中，放置在温度为22～24℃，相对湿度为60％，光照时间为14:10h的实验室中继续饲养，24h后记录死亡情况，每一实验重复三次，并用下列公式计算校正死亡率：
4、淡色库蚊的测定方法
采用世界卫生组织推荐的方法，将待测样品溶解于二甲亚砜并用0.1％吐温-80水溶液稀释成一定的浓度，以不加待测样品的相应溶液为阴性对照。取每种溶液1mL，分别加入到装有99mL蒸馏水和20头淡色库蚊3龄幼虫的118mL蜡质纸杯中，将这些纸杯放置在温度为22～24℃，相对湿度为60％，光照时间为14:10h的实验室中继续饲养，24h后记录死亡情况，每一实验重复三次，并用下列公式计算校正死亡率：
5、试验结果
本发明化合物的杀虫结果见表1。
表1
a：三次重复的平均值。
从上表1可知，本发明化合物对粘虫、朱砂叶螨和淡色库蚊都有较好的毒杀活性。
试验例2本发明化合物的抗氧化性能的测定
1、仪器与试剂
721B型分光光度计，1，1-二苯基-2-苦基肼(DPPH)，95％乙醇。
2、测定步骤
(1)DPPH及样品溶液的配制
用分析天平准确称取0.0130克DPPH，用95％乙醇定容至500mL容量瓶中，得到浓度为26mg/L的溶液；准确称取0.0100g待测样品，用95％乙醇定容至100mL容量瓶中，得到浓度为100mg/L的样品溶液。
(2)在10mL锥形瓶中依次加入4mL的DPPH溶液和1mL95％乙醇溶液，混匀反应稳定后，以95％乙醇为参比溶液，在λmax＝518nm处测定其吸光度值，记为A0。
(3)在10mL锥形瓶中依次加入4mL的DPPH溶液和1mL待测溶液，摇匀，在室温下反应40min稳定后，以95％乙醇为参比溶液，在波长λmax＝518nm处测定其吸光度值，记为AS。每一实验重复三次，并用下列公式计算抗氧化剂的自由基清除率Y(％)：
3、抗氧化性能的测定结果
测定结果见表2。
表2在浓度为100mg/L时，化合物对DPPH自由基的清除率
化合物 清除率<sup>a</sup>(％)
化合物1 91.0
化合物2 93.8
化合物3 80.3
化合物4 82.6
化合物5 94.1
化合物6 90.8
a：三次重复的平均值。
从上表2可知，本发明化合物对DPPH自由基的清除率都在80％以上，即它们都有较好的抗氧化性能。

Claims (6)

1.结构式如式Ⅰ所示的化合物：
其中，R1为R2为氢或卤素；R3为氢或卤素；X为O或S。
2.根据权利要求1所述的化合物，其特征在于：R1为
3.根据权利要求1或2所述的化合物，其特征在于，结构式如式Ⅰ-1或式Ⅰ-2所示：
4.根据权利要求1所述的化合物，其特征在于，其结构式如下：
5.权利要求1～4任一项所述的化合物在制备抗氧化剂中的应用。
6.权利要求1～4任一项所述的化合物在防治农业害虫中的应用，其特征在于：所述农业害虫为粘虫、朱砂叶螨或淡色库蚊。
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