新型樟脑酸衍生物的合成及生物活性研究
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摘要
樟脑是一种双环单萜类非木质林产品,是我国的天然优势资源,也可由松节油的主要成分α-蒎烯经多步反应合成得到。樟脑本身具有广泛的生物活性。将樟脑氧化可得到樟脑酸。樟脑酸及其衍生物表现出多种生物活性。本文以樟脑酸为原料,先将樟脑酸脱水得到樟脑酸酐,然后通过肼或乙二胺分子搭桥,将酰腙、硫脲、磺酰胺和酰肼等生物活性基团引入到樟脑酸分子骨架中去,设计和合成四类具有潜在生物活性的新型樟脑酸衍生物,为樟脑酸的深度开发和利用提供新的途径。
本文以樟脑酸为原料,合成了49个新型的樟脑酸衍生物。初步探索了合成条件,利用FT-IR、1H NMR、13C NMR、ESI-MS、HSQC和NOESY等多种方法对所有新化合物进行了结构表征。还测试了目标化合物在杀菌和除草方面的生物活性。主要研究内容和研究成果如下：
1.以樟脑酸为原料,经乙酸酐脱水得到樟脑酸酐,再与水合肼进行酰化反应制备N-氨基樟脑酰亚胺,继而在微波辐照和冰醋酸催化下与各种取代苯甲醛缩合,合成得到18个未见文献报道的樟脑酸基酰腙化合物4a-4r。
2.以樟脑酸为原料,经乙酸酐脱水制备樟脑酸酐；以取代苯胺为原料制备取代苯基异硫氰酸酯,然后与乙二胺反应得到氨乙基取代苯基硫脲；最后将樟脑酸酐与氨乙基取代苯基硫脲反应,合成得到10个未见文献报道的樟脑酸基硫脲化合物7a-7j。
3.以樟脑酸为原料,经乙酸酐脱水制备樟脑酸酐；通过苯磺酰氯与乙二胺反应制备N-苯磺酰基乙二胺；最后将樟脑酸酐与N-苯磺酰基乙二胺反应,合成得到11个未见文献报道的樟脑酸基磺酰胺化合物9a-9k。
4.以樟脑酸为原料,经乙酸酐脱水制备樟脑酸酐,然后与芳酰肼发生N-酰化反应,合成得到10个未见文献报道的樟脑酸基双酰肼化合物10a～10j。
5.采用离体法测试了所有目标化合物的杀菌活性。发现在50mg·L-1浓度下,樟脑酸基酰腙化合物4f(R=o-Br)、4g(R=p-Br)、4m (R=p-OCH3)、4p (R=p-OH)、4a(R=H)、4h (R=o-NO2)、4i (R=m-NO2)、4k (R=o-OCH3)、4n (R=o-OH),樟脑酸基磺酰胺化合物9a(R=H)、9e(R=m-OCH3),以及樟脑酸基双酰肼化合物10h (R=β-Pyridyl)、10b (R=p-NO2Ph)、10i (R=γ-Pyridyl)、10a (R=Ph)、10g (R=p-FPh),等十六个目标化合物对苹果轮纹病菌的抑制活性显著,抑制率均达90.0%以上。樟脑酸基硫脲化合物7c (R=o-OCH3)、7d (R=m-OCH3)和9h(R=p-Cl)等三个目标化合物对番茄早疫病菌具有良好的抑制作用,抑制率均达86.9%。樟脑酸基酰腙化合物4k (R=o-OCH3)、4a (R=H)和4h (R=o-NO2)等三个目标化合物小麦赤霉病菌具有良好的抑制作用,抑制率在80%-85%之间。其余化合物对五种供试植物病原菌的抑制作用不明显。
6.采用油菜平皿法和稗草小杯法测试了所有目标化合物的除草活性。发现在100mg·L-1浓度下,樟脑酸基酰腙化合物4j(R=p-Br)和4r (R=p-Cl)以及中间体2对油菜的胚根生长显示良好的抑制活性,抑制率分别为91.6%、91.4%和86.8%,其余目标化合物对油菜胚根生长的抑制作用不明显。所有目标化合物对稗草幼苗生长的抑制活性均不理想。
Camphor is a nonwood forest product with bicyclic monoterpene structure. As a natural and preponderant resource of China, it can also be synthesized via several reaction steps from a-pinene which is the dominant component of turpentine. Camphor itself exhibits a wide range of bioactivities. Camphoric acid, the oxidation product of camphor, and its derivatives have been found to show various bioactivities. In this thesis, camphoric anhydride was prepared by using camphoric acid as starting material and acetic anhydride as dehydrating agent. Then, four types of novel camphoric acid derivatives with potential bioactivity were designed and synthesized by building a bridge with hydrazine or ethyienediamine molecule, and by introducing of acylhydrazone, thiourea, sulfonamide and diacylhydrazine groups into the molecular skeleton of camphoric acid. This research aims at providing a new way for the deep development and utilization of camphoric acid.
In this thesis, forty-nine novel camphoric acid derivatives were synthesized using camphoric acid as starting material. The synthetic conditions were investigated preliminarily. The novel compounds were characterized by means of FT-IR,'H NMR,13C NMR, ESI-MS, HSQC and NOESY techniques. Furthermore, fungicidal and herbicidal bioactivities were evaluated for the target compounds. The main research contens and results are shown as follows:
1. Camphoric anhydride was prepared by using camphoric acid as starting material and acetic anhydride as dehydrating agent. Then, N-amino camphorimide was prepared by the N-acylation reaction of camphoric anhydride with hydrazine hydrate, followed by the condensation reaction of N-amino camphorimide with substituted phenyl aldehydes in the presence of glacial acetic acid as catalyst and under microwave irradiation to afford eighteen novel camphoric acid-based acylhydrazone compounds4a-4r.
2. Camphoric anhydride was prepared by using camphoric acid as starting material and acetic anhydride as dehydrating agent. Then, aminoethyl substituted phenyl thioureas were synthesized by the reaction of ethylenediamine with substituted phenyl isothiocyanides which were converted from the corresponding substituted anilines, followed by the reaction of camphoric anhydride with aminoethyl substituted phenyl thioureas to yield ten novel camphoric acid-based thiourea compounds7a-7j.
3. Camphoric anhydride was prepared by using camphoric acid as starting material and acetic anhydride as dehydrating agent. Then, N-aryl sulfonyl ethyenediamines were synthesized by the reaction of ethylenediamine with substituted benzenesulfonyl chlorides, followed by the reaction of camphoric anhydride with N-aryl sulfonyl ethyenediamines to obtain eleven novel camphoric acid-based benzene-sulfonamide compounds9a-9k.
4. Camphoric anhydride was prepared by using camphoric acid as starting material and acetic anhydride as dehydrating agent. Then, ten novel camphoric acid-based diacylhydrazine compounds10a-10j were synthesized by the N-acylation reaction of camphoric anhydride with aryl acylhydrazines.
5. The fungicidal activity of all the target compounds was evaluated by disc method in vitro. It was found that, at the concentration of50mg·L-1, sixteen target compounds, including camphoric acid-based acylhydrazone compounds 4f (R=o-Br),4g (R=p-Br),4m (R=p-OCH3),4p (R=p-OH),4a (R=H),4h (R=o-NO2),4i (R=m-NO2),4k (R=o-OCH3), and4n (R=o-OH), camphoric acid-based benzenesulfonamide compounds9a (R=H) and9e (R=m-OCH3), camphoric acid-based diacylhydrazine compounds10h (R=β-Pyridyl),10b (R=p-NO2Ph),10i (R=y-Pyridyl),10a (R=Ph), and10g (R=p-FPh), exhibited prominent inhibition activity against Physalospora piricola, which had inhibition rates of≥90.0%. Camphoric acid-based thiourea compounds7c (R=o-OCH3),7d (R=m-OCH3) and9h (R=p-Cl) showed good inhibition activity against Alternaria solani, and had inhibition rate of86.9%. Camphoric acid-based acylhydrazone compounds4k (R=o-OCH3),4a (R=H) and4h (R=o-NO2) displayed good inhibition activity against Gibberella zeaey and had inhibition rates of80%～85%of86.9%. The other target compounds did not show obvious inhibition activity against the five tested fungi.
6. The herbicidal activity of all the target compounds was evaluated by rape petri dish method and barnyard grass beaker method. It was found that, at the concentration of100mg·L-1, camphoric acid-based acylhydrazone compounds4j (R=p-Br),4r (R=p-Cl), and the intermediate2exhibited good growth inhibition activity against root of rape (Brassica campestris), and had inhibition rates of91.6%,91.4%, and86.8%, respectively. The other target compounds did not show obvious growth inhibition activity against root of rape (Brassica campestris). All the target compounds only displayed weak growth inhibition activity against barnyard grass (Echinochloa crusgalli (L.)).
本文以樟脑酸为原料,合成了49个新型的樟脑酸衍生物。初步探索了合成条件,利用FT-IR、1H NMR、13C NMR、ESI-MS、HSQC和NOESY等多种方法对所有新化合物进行了结构表征。还测试了目标化合物在杀菌和除草方面的生物活性。主要研究内容和研究成果如下：
1.以樟脑酸为原料,经乙酸酐脱水得到樟脑酸酐,再与水合肼进行酰化反应制备N-氨基樟脑酰亚胺,继而在微波辐照和冰醋酸催化下与各种取代苯甲醛缩合,合成得到18个未见文献报道的樟脑酸基酰腙化合物4a-4r。
2.以樟脑酸为原料,经乙酸酐脱水制备樟脑酸酐；以取代苯胺为原料制备取代苯基异硫氰酸酯,然后与乙二胺反应得到氨乙基取代苯基硫脲；最后将樟脑酸酐与氨乙基取代苯基硫脲反应,合成得到10个未见文献报道的樟脑酸基硫脲化合物7a-7j。
3.以樟脑酸为原料,经乙酸酐脱水制备樟脑酸酐；通过苯磺酰氯与乙二胺反应制备N-苯磺酰基乙二胺；最后将樟脑酸酐与N-苯磺酰基乙二胺反应,合成得到11个未见文献报道的樟脑酸基磺酰胺化合物9a-9k。
4.以樟脑酸为原料,经乙酸酐脱水制备樟脑酸酐,然后与芳酰肼发生N-酰化反应,合成得到10个未见文献报道的樟脑酸基双酰肼化合物10a～10j。
5.采用离体法测试了所有目标化合物的杀菌活性。发现在50mg·L-1浓度下,樟脑酸基酰腙化合物4f(R=o-Br)、4g(R=p-Br)、4m (R=p-OCH3)、4p (R=p-OH)、4a(R=H)、4h (R=o-NO2)、4i (R=m-NO2)、4k (R=o-OCH3)、4n (R=o-OH),樟脑酸基磺酰胺化合物9a(R=H)、9e(R=m-OCH3),以及樟脑酸基双酰肼化合物10h (R=β-Pyridyl)、10b (R=p-NO2Ph)、10i (R=γ-Pyridyl)、10a (R=Ph)、10g (R=p-FPh),等十六个目标化合物对苹果轮纹病菌的抑制活性显著,抑制率均达90.0%以上。樟脑酸基硫脲化合物7c (R=o-OCH3)、7d (R=m-OCH3)和9h(R=p-Cl)等三个目标化合物对番茄早疫病菌具有良好的抑制作用,抑制率均达86.9%。樟脑酸基酰腙化合物4k (R=o-OCH3)、4a (R=H)和4h (R=o-NO2)等三个目标化合物小麦赤霉病菌具有良好的抑制作用,抑制率在80%-85%之间。其余化合物对五种供试植物病原菌的抑制作用不明显。
6.采用油菜平皿法和稗草小杯法测试了所有目标化合物的除草活性。发现在100mg·L-1浓度下,樟脑酸基酰腙化合物4j(R=p-Br)和4r (R=p-Cl)以及中间体2对油菜的胚根生长显示良好的抑制活性,抑制率分别为91.6%、91.4%和86.8%,其余目标化合物对油菜胚根生长的抑制作用不明显。所有目标化合物对稗草幼苗生长的抑制活性均不理想。
Camphor is a nonwood forest product with bicyclic monoterpene structure. As a natural and preponderant resource of China, it can also be synthesized via several reaction steps from a-pinene which is the dominant component of turpentine. Camphor itself exhibits a wide range of bioactivities. Camphoric acid, the oxidation product of camphor, and its derivatives have been found to show various bioactivities. In this thesis, camphoric anhydride was prepared by using camphoric acid as starting material and acetic anhydride as dehydrating agent. Then, four types of novel camphoric acid derivatives with potential bioactivity were designed and synthesized by building a bridge with hydrazine or ethyienediamine molecule, and by introducing of acylhydrazone, thiourea, sulfonamide and diacylhydrazine groups into the molecular skeleton of camphoric acid. This research aims at providing a new way for the deep development and utilization of camphoric acid.
In this thesis, forty-nine novel camphoric acid derivatives were synthesized using camphoric acid as starting material. The synthetic conditions were investigated preliminarily. The novel compounds were characterized by means of FT-IR,'H NMR,13C NMR, ESI-MS, HSQC and NOESY techniques. Furthermore, fungicidal and herbicidal bioactivities were evaluated for the target compounds. The main research contens and results are shown as follows:
1. Camphoric anhydride was prepared by using camphoric acid as starting material and acetic anhydride as dehydrating agent. Then, N-amino camphorimide was prepared by the N-acylation reaction of camphoric anhydride with hydrazine hydrate, followed by the condensation reaction of N-amino camphorimide with substituted phenyl aldehydes in the presence of glacial acetic acid as catalyst and under microwave irradiation to afford eighteen novel camphoric acid-based acylhydrazone compounds4a-4r.
2. Camphoric anhydride was prepared by using camphoric acid as starting material and acetic anhydride as dehydrating agent. Then, aminoethyl substituted phenyl thioureas were synthesized by the reaction of ethylenediamine with substituted phenyl isothiocyanides which were converted from the corresponding substituted anilines, followed by the reaction of camphoric anhydride with aminoethyl substituted phenyl thioureas to yield ten novel camphoric acid-based thiourea compounds7a-7j.
3. Camphoric anhydride was prepared by using camphoric acid as starting material and acetic anhydride as dehydrating agent. Then, N-aryl sulfonyl ethyenediamines were synthesized by the reaction of ethylenediamine with substituted benzenesulfonyl chlorides, followed by the reaction of camphoric anhydride with N-aryl sulfonyl ethyenediamines to obtain eleven novel camphoric acid-based benzene-sulfonamide compounds9a-9k.
4. Camphoric anhydride was prepared by using camphoric acid as starting material and acetic anhydride as dehydrating agent. Then, ten novel camphoric acid-based diacylhydrazine compounds10a-10j were synthesized by the N-acylation reaction of camphoric anhydride with aryl acylhydrazines.
5. The fungicidal activity of all the target compounds was evaluated by disc method in vitro. It was found that, at the concentration of50mg·L-1, sixteen target compounds, including camphoric acid-based acylhydrazone compounds 4f (R=o-Br),4g (R=p-Br),4m (R=p-OCH3),4p (R=p-OH),4a (R=H),4h (R=o-NO2),4i (R=m-NO2),4k (R=o-OCH3), and4n (R=o-OH), camphoric acid-based benzenesulfonamide compounds9a (R=H) and9e (R=m-OCH3), camphoric acid-based diacylhydrazine compounds10h (R=β-Pyridyl),10b (R=p-NO2Ph),10i (R=y-Pyridyl),10a (R=Ph), and10g (R=p-FPh), exhibited prominent inhibition activity against Physalospora piricola, which had inhibition rates of≥90.0%. Camphoric acid-based thiourea compounds7c (R=o-OCH3),7d (R=m-OCH3) and9h (R=p-Cl) showed good inhibition activity against Alternaria solani, and had inhibition rate of86.9%. Camphoric acid-based acylhydrazone compounds4k (R=o-OCH3),4a (R=H) and4h (R=o-NO2) displayed good inhibition activity against Gibberella zeaey and had inhibition rates of80%～85%of86.9%. The other target compounds did not show obvious inhibition activity against the five tested fungi.
6. The herbicidal activity of all the target compounds was evaluated by rape petri dish method and barnyard grass beaker method. It was found that, at the concentration of100mg·L-1, camphoric acid-based acylhydrazone compounds4j (R=p-Br),4r (R=p-Cl), and the intermediate2exhibited good growth inhibition activity against root of rape (Brassica campestris), and had inhibition rates of91.6%,91.4%, and86.8%, respectively. The other target compounds did not show obvious growth inhibition activity against root of rape (Brassica campestris). All the target compounds only displayed weak growth inhibition activity against barnyard grass (Echinochloa crusgalli (L.)).
引文
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