天然樟脑是我国的天然优势资源,合成樟脑可由松节油的主要成分α-蒎烯经多步反应合成得到。樟脑及其衍生物具有多种生物活性,通过对樟脑分子的结构修饰可以合成许多具有生物活性的衍生物。以D-(+)-樟脑磺酸为原料,经多步反应合成了11个...天然樟脑是我国的天然优势资源,合成樟脑可由松节油的主要成分α-蒎烯经多步反应合成得到。樟脑及其衍生物具有多种生物活性,通过对樟脑分子的结构修饰可以合成许多具有生物活性的衍生物。以D-(+)-樟脑磺酸为原料,经多步反应合成了11个新型的N′-取代苯磺酰基-N-樟脑磺酰乙二胺化合物(4a~4k),其结构经傅里叶红外光谱(FT-IR)、核磁共振氢谱(1 H NMR)、核磁共振碳谱(13 C NMR)和电喷雾电离质谱(ESI-MS)表征。采用离体法测定了目标化合物的抗真菌活性。实验结果表明:在50μg/mL质量浓度下,目标化合物对黄瓜枯萎病菌、苹果轮纹病菌、番茄早疫病菌、花生褐斑病菌和小麦赤霉病菌等5种植物病原菌有一定的抗菌活性,其中化合物4b(R=p-OCH 3)、4a(R=H)、4c(R=m-OCH 3)和4d(R=m-CH 3)对番茄早疫病菌的抑制率分别为91.3%,83.9%,83.9%和83.9%(均达B级以上活性水平),均优于阳性对照百菌清(73.9%);化合物4b和4c对花生褐斑病菌的抑制率均为82.2%(B级活性水平),优于阳性对照百菌清(73.3%);此外,化合物4b对黄瓜枯萎病菌的抑制率达到90.8%(A级活性水平)。由此可知,化合物4b显示出了广谱的抑菌活性,值得进一步研究。展开更多
将α-蒎烯选择性氧化制备马鞭草烯酮,对羰基进行肟化和分离,再发生亲核取代反应,合成得到40个新型( Z )-/( E )-马鞭草烯酮肟醚(4a ~4t ,包括20对 Z / E 异构体),采用 1 H NMR、 13 C NMR 、FT-IR、UV-vis和ESI-MS对目标化合物进行了结...将α-蒎烯选择性氧化制备马鞭草烯酮,对羰基进行肟化和分离,再发生亲核取代反应,合成得到40个新型( Z )-/( E )-马鞭草烯酮肟醚(4a ~4t ,包括20对 Z / E 异构体),采用 1 H NMR、 13 C NMR 、FT-IR、UV-vis和ESI-MS对目标化合物进行了结构表征,并测试其抑菌活性。研究结果表明:在质量浓度50 mg/L下,目标化合物对8种植物病原菌均显示出不同程度的抑菌活性,其中化合物( E )- 4r (R=2,6-Cl)对苹果轮纹病菌的抑制率为77.8%,化合物( E )- 4s (R=2,6-F)对水稻纹枯病菌的抑制率为72.7%,化合物( E )- 4n (R= p -CN)对玉米小斑病菌的抑制率为70.8%,( Z )-/( E )-异构体对一些植物病原菌的抑制活性显示一定差异。建立了( E )-马鞭草烯酮肟醚化合物对水稻纹枯病菌抑制活性的CoMFA模型( r 2 =0.992, q 2 =0.507),进行3D-QSAR研究,结果表明建立的模型可用于设计具有潜在高活性的先导化合物。展开更多
In search of natural renewable resource-based bioactive molecules,20 hydroxamate inhibitors were designed and synthesized using cinamaldehyde as the starting material.Their structures were characterized by FT-IR,^(1)H...In search of natural renewable resource-based bioactive molecules,20 hydroxamate inhibitors were designed and synthesized using cinamaldehyde as the starting material.Their structures were characterized by FT-IR,^(1)HNMR,^(13)C NMR,and HRMS.And in vitro antifungal activity of the target compounds against 8 tested fungi was preliminarily evaluated by the agar dilution method.The bioassay results revealed that at the concentration of 50 mg/L,the target compounds exhibited certain inhibitory activity against 8 tested fungi,in which compounds 5r(R=o,o-Cl),5c(R=m-F),5b(R=o-F)and 5p(R=o,p-Cl)displayed better inhibitory activity of 93.3%,76.8%,75.3%and 72.3%,respectively,against P.piricola than that of the positive control chlorothalonil.At the same time,3D-quantitative structure-activity relationship(3D-QSAR)study was carried out to explore the relationship of the molecular structures with their antifungal activity against P.piricola.And a reasonable and effective 3D-QSAR model(r^(2)=0.980,q^(2)=0.501)has been established.Besides,molecular docking was also performed to reveal the binding mode of the target compound 5r(R=o,o-Cl)with succinate dehydrogenase(SDH).It was found that compound 5r could be well embedded in the active pocket of the receptor protein.This showed a similar mode with SDH inhibitors(SDHI)carboxin.展开更多
文摘天然樟脑是我国的天然优势资源,合成樟脑可由松节油的主要成分α-蒎烯经多步反应合成得到。樟脑及其衍生物具有多种生物活性,通过对樟脑分子的结构修饰可以合成许多具有生物活性的衍生物。以D-(+)-樟脑磺酸为原料,经多步反应合成了11个新型的N′-取代苯磺酰基-N-樟脑磺酰乙二胺化合物(4a~4k),其结构经傅里叶红外光谱(FT-IR)、核磁共振氢谱(1 H NMR)、核磁共振碳谱(13 C NMR)和电喷雾电离质谱(ESI-MS)表征。采用离体法测定了目标化合物的抗真菌活性。实验结果表明:在50μg/mL质量浓度下,目标化合物对黄瓜枯萎病菌、苹果轮纹病菌、番茄早疫病菌、花生褐斑病菌和小麦赤霉病菌等5种植物病原菌有一定的抗菌活性,其中化合物4b(R=p-OCH 3)、4a(R=H)、4c(R=m-OCH 3)和4d(R=m-CH 3)对番茄早疫病菌的抑制率分别为91.3%,83.9%,83.9%和83.9%(均达B级以上活性水平),均优于阳性对照百菌清(73.9%);化合物4b和4c对花生褐斑病菌的抑制率均为82.2%(B级活性水平),优于阳性对照百菌清(73.3%);此外,化合物4b对黄瓜枯萎病菌的抑制率达到90.8%(A级活性水平)。由此可知,化合物4b显示出了广谱的抑菌活性,值得进一步研究。
文摘将α-蒎烯选择性氧化制备马鞭草烯酮,对羰基进行肟化和分离,再发生亲核取代反应,合成得到40个新型( Z )-/( E )-马鞭草烯酮肟醚(4a ~4t ,包括20对 Z / E 异构体),采用 1 H NMR、 13 C NMR 、FT-IR、UV-vis和ESI-MS对目标化合物进行了结构表征,并测试其抑菌活性。研究结果表明:在质量浓度50 mg/L下,目标化合物对8种植物病原菌均显示出不同程度的抑菌活性,其中化合物( E )- 4r (R=2,6-Cl)对苹果轮纹病菌的抑制率为77.8%,化合物( E )- 4s (R=2,6-F)对水稻纹枯病菌的抑制率为72.7%,化合物( E )- 4n (R= p -CN)对玉米小斑病菌的抑制率为70.8%,( Z )-/( E )-异构体对一些植物病原菌的抑制活性显示一定差异。建立了( E )-马鞭草烯酮肟醚化合物对水稻纹枯病菌抑制活性的CoMFA模型( r 2 =0.992, q 2 =0.507),进行3D-QSAR研究,结果表明建立的模型可用于设计具有潜在高活性的先导化合物。
文摘In search of natural renewable resource-based bioactive molecules,20 hydroxamate inhibitors were designed and synthesized using cinamaldehyde as the starting material.Their structures were characterized by FT-IR,^(1)HNMR,^(13)C NMR,and HRMS.And in vitro antifungal activity of the target compounds against 8 tested fungi was preliminarily evaluated by the agar dilution method.The bioassay results revealed that at the concentration of 50 mg/L,the target compounds exhibited certain inhibitory activity against 8 tested fungi,in which compounds 5r(R=o,o-Cl),5c(R=m-F),5b(R=o-F)and 5p(R=o,p-Cl)displayed better inhibitory activity of 93.3%,76.8%,75.3%and 72.3%,respectively,against P.piricola than that of the positive control chlorothalonil.At the same time,3D-quantitative structure-activity relationship(3D-QSAR)study was carried out to explore the relationship of the molecular structures with their antifungal activity against P.piricola.And a reasonable and effective 3D-QSAR model(r^(2)=0.980,q^(2)=0.501)has been established.Besides,molecular docking was also performed to reveal the binding mode of the target compound 5r(R=o,o-Cl)with succinate dehydrogenase(SDH).It was found that compound 5r could be well embedded in the active pocket of the receptor protein.This showed a similar mode with SDH inhibitors(SDHI)carboxin.
