蒎酮酸衍生物的合成、表征及生物活性研究
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摘要
天然资源原料具有独特和新颖的结构,以其为先导化合物进行分子修饰,合成新型的生物活性物质,是天然资源的重要研究方向。我国具有丰富的松节油资源,其主要成分为α-蒎烯。α-蒎烯具有来源丰富、价格便宜、性质活泼等优势,由其衍生得到的产品被广泛应用于国民经济的各个领域。
本文以α-蒎烯为原料,经氧化合成2-(3-乙酰基-2, 2-二甲基环丁基)乙酸(蒎酮酸),再以蒎酮酸为原料合成了六类共62个含四元环结构的化合物,其中45个为首次合成。采用IR、MS、1H NMR以及单晶X射线四圆衍射等方法对所合成的产品进行结构解析,并对合成的产品进行抑菌、驱避、杀虫等生物活性测试,初步探讨了产品的构效关系,为今后进一步开发新型的生物活性物质奠定了基础。
以α-蒎烯为原料,高锰酸钾为氧化剂、硫酸铵为pH调节剂、水为反应介质合成了蒎酮酸,再通过酰基化、羟醛缩合、酯化、亲核取代、亲核加成等反应合成了酰胺、α,β-不饱和羰基化合物、酯类、酰基硫脲四类共38个化合物,其中22个为新物质。首次得到了三种蒎酮酰胺类化合物的单晶,并解析了它们的晶体结构,晶体数据表明产品中的环丁烷结构是非平面的,沿其中的两个碳原子呈折叠状态,为半椅式结构。
以蒎酮酸为原料,经Wolff-Kishner还原反应合成了(2, 2-二甲基-3-乙基环丁基)乙酸,再经酰氯化、亲核取代、亲核加成反应,生成了十三种酰基硫脲衍生物,其中十二种物质为首次合成。首次得到了三个化合物的单晶,并解析了它们的晶体结构。
以蒎酮酸为原料,经Willgerodt反应合成了2, 2-二甲基环丁基-1, 3-二乙酸(高蒎酸),再经酰氯化、亲核取代、亲核加成反应,合成了十一种未见文献报道的双酰基硫脲衍生物。
采用药剂喷雾法测试了三种酰基硫脲化合物对烟粉虱(Bemisia tabaci)的杀虫活性;采用人工饲料法测试了六类物质37种产品对亚洲玉米螟(Ostrinia furnacalis)的杀虫活性;采用滤纸浸液法测试了在100 mg/mL浓度下八种蒎酮酰胺化合物对家蝇(Musca domestica)的驱避活性;采用种子浸液法测试了在100 mg/mL浓度下八种蒎酮酰胺化合物对小黄家蚁(Monomorium pharaonis)的驱避活性;测试了八种蒎酮酸酯和十二种酰基硫脲类化合物对白纹伊蚊(Aedes albopictus)的驱避活性;采用最低抑菌浓度法测试了15种蒎酮酰胺类物质和9种α,β-不饱和羰基化合物对产气杆菌(Clostridium perfringens)、伤寒杆菌(Salmonella typhi)、肺炎克雷伯杆菌(K. peneumoniae)、绿脓杆菌(P. aeruginosa)、大肠杆菌(E. coli)、表皮葡萄球菌(Staph. Epidermidis)和金黄色葡萄球菌(Staph. aureus)的抑菌活性;。
蒎酮酸甲酯(4a)、蒎酮酸乙酯(4b)和蒎酮酸正戊酯(4f)对白纹伊蚊表现出较好的驱避活性,在200 mg/mL浓度时对白纹伊蚊的驱避时间达到2.5 ~ 3.0 h;(2, 2-二甲基-3-乙基环丁基)乙酸与取代苯胺生成的酰基硫脲表现出较好的杀虫活性,其中1-[2-(3-乙基-2, 2-二甲基环丁基)乙酰基]-3-(2-甲基苯基)硫脲(6b)、1-[2-(3-乙基-2, 2-二甲基环丁基)乙酰基]-3-(4-三氟甲基苯基)硫脲(6h)、1-[2-(3-乙基-2, 2-二甲基环丁基)乙酰基]-3-(2-氯苯基)硫脲(6i)、1-[2-(3-乙基-2, 2-二甲基环丁基)乙酰基]-3-(4-氯苯基)硫脲(6j)的杀虫活性较好,在1 g/kg浓度下对亚洲玉米螟的校正死亡率在93.1%以上。因此,蒎酮酸酯和酰基硫脲化合物具有进一步开发研究用以筛选新型驱避剂和杀虫剂的应用价值。
Molecular modification of natural resources materials with unique and novel structure to produce bioacitive compounds is an impotant direction of natural product research. There is abundant resource of turpentine in China, the major component of which isα-pinene.α-Pinene has been widely used as raw material for the production of some compounds necessary for national economy due to its abundant availability, low cost and active configuration.
Sixty two compounds with six kinds were synthesized from 2-(3-acetyl-2, 2-dimethylcyclobutyl)acetic acid (pinonic acid) which was obtained from the oxidation ofα-pinene. Among them 45 compounds were synthesized for the first time. Their structures were characterized by IR, MS, 1H NMR and X-ray diffraction. The antibacterial, repellent and insecticidal activities of the synthetic derivatives were studies in this paper. The structure activity relationships were also studied. This work might lay a solid foundation for further research of new bioacitive compounds.
Pinonic acid was synthesized usingα-pinene as raw material, potassium permanganate as oxidant, ammonium sulfate as pH regulator and water as reaction medium. Then 38 compounds of amides,α,β-unsaturated carbonyl compounds, esters and acylthioureas were synthesized through acylation, aldol condensation, esterification, nucleophilic substitution, nucleophilic addition reactions and so on. Among them 22 compounds were synthesized for the first time. The single crystals of three pinonamides were obtained and their crystal structures were analysed. The cyclobutane fragment of the products was not flat and was flexed as though folded from the dimethylsubstituted C atom to the unsubstituted C atom. The conformation of the cyclobutane represented semi-chair.
Thirteen acylthioureas were obtained through acylchlorination, nucleophilic substitution, nucleophilic addition reaction from (2, 2-dimethyl-3-ethylcyclobutyl)acetic acid which was obtained from pinonic acid via Wolff-Kishner reaction. The single crystals of three acylthioureas were obtained and their crystal structures were analysed.
Eleven new diacylthioureas were obtained through acylchlorination, nucleophilic substitution, nucleophilic addition reaction from 2, 2-dimethylcyclobutyl-1, 3-diacetic acid (sym-homopinic acid) which was obtained from pinonic acid via Willgerodt reaction.
The insecticidal activities of three acylthioureas against Bemisia tabaci were test by medicament spraying method. The insecticidal activities of 37 products with six kinds against Ostrinia furnacalis were tested by artificial diet method. The repellent activities of eight kinds of pinonamides against Musca domestica were tested at the concentration of 100 mg/mL by dipped filter paper mathod. The repellent activities of eight kinds of pinonamides against Monomorium pharaonis were tested at the concentration of 100 mg/mL by dipped seeds method. The repellent activities of eight esters and twelve acylthioureas against Aedes albopictus were tested at the concentration of 100 mg/mL. The antibacterial acitivities of 15 pinonamides and 9α,β-unsaturated carbonyl compounds against Clostridium perfringens, Salmonella typhi, K. peneumoniae, P. aeruginosa, E. coli, Staph. Epidermidis and Staph. aureus were tested by minimum inhibitory concentration method.
Methyl ester, ethyl ester and pentyl ester of pinonic acid have higher repellent activities against Aedes albopictus. The repellent time of them are up to 2.5 ~ 3.0 h at the concentration of 200 mg/mL. The acylthioureas obtained from (2, 2-dimethylcyclobutyl)acetic acid have better insecticidal activities against Ostrinia furnacalis. Among these acylthioureas the insecticidal acitivities of 1-[2-(3-ethyl-2, 2-dimethylcyclobutyl)acetyl]-3-o-tolylthiourea (6b), 1-[2-(3-ethyl-2, 2-dimethylcyclobutyl)acetyl]-3-(4-trifluoromethylphenyl)thiourea (6h), 1-[2-(3-ethyl-2, 2-dimethylcyclobutyl)acetyl]-3-(2-chlorophenyl)thiourea (6i), 1-[2-(3-ethyl-2, 2-dimethylcyclobutyl)acetyl]-3-(4-chlorophenyl)thiourea (6j) are better than that of other compounds. So esters and acylthioureas derivatives of pinonic acid have potential for further research to explore new repellants and insecticides.
本文以α-蒎烯为原料,经氧化合成2-(3-乙酰基-2, 2-二甲基环丁基)乙酸(蒎酮酸),再以蒎酮酸为原料合成了六类共62个含四元环结构的化合物,其中45个为首次合成。采用IR、MS、1H NMR以及单晶X射线四圆衍射等方法对所合成的产品进行结构解析,并对合成的产品进行抑菌、驱避、杀虫等生物活性测试,初步探讨了产品的构效关系,为今后进一步开发新型的生物活性物质奠定了基础。
以α-蒎烯为原料,高锰酸钾为氧化剂、硫酸铵为pH调节剂、水为反应介质合成了蒎酮酸,再通过酰基化、羟醛缩合、酯化、亲核取代、亲核加成等反应合成了酰胺、α,β-不饱和羰基化合物、酯类、酰基硫脲四类共38个化合物,其中22个为新物质。首次得到了三种蒎酮酰胺类化合物的单晶,并解析了它们的晶体结构,晶体数据表明产品中的环丁烷结构是非平面的,沿其中的两个碳原子呈折叠状态,为半椅式结构。
以蒎酮酸为原料,经Wolff-Kishner还原反应合成了(2, 2-二甲基-3-乙基环丁基)乙酸,再经酰氯化、亲核取代、亲核加成反应,生成了十三种酰基硫脲衍生物,其中十二种物质为首次合成。首次得到了三个化合物的单晶,并解析了它们的晶体结构。
以蒎酮酸为原料,经Willgerodt反应合成了2, 2-二甲基环丁基-1, 3-二乙酸(高蒎酸),再经酰氯化、亲核取代、亲核加成反应,合成了十一种未见文献报道的双酰基硫脲衍生物。
采用药剂喷雾法测试了三种酰基硫脲化合物对烟粉虱(Bemisia tabaci)的杀虫活性;采用人工饲料法测试了六类物质37种产品对亚洲玉米螟(Ostrinia furnacalis)的杀虫活性;采用滤纸浸液法测试了在100 mg/mL浓度下八种蒎酮酰胺化合物对家蝇(Musca domestica)的驱避活性;采用种子浸液法测试了在100 mg/mL浓度下八种蒎酮酰胺化合物对小黄家蚁(Monomorium pharaonis)的驱避活性;测试了八种蒎酮酸酯和十二种酰基硫脲类化合物对白纹伊蚊(Aedes albopictus)的驱避活性;采用最低抑菌浓度法测试了15种蒎酮酰胺类物质和9种α,β-不饱和羰基化合物对产气杆菌(Clostridium perfringens)、伤寒杆菌(Salmonella typhi)、肺炎克雷伯杆菌(K. peneumoniae)、绿脓杆菌(P. aeruginosa)、大肠杆菌(E. coli)、表皮葡萄球菌(Staph. Epidermidis)和金黄色葡萄球菌(Staph. aureus)的抑菌活性;。
蒎酮酸甲酯(4a)、蒎酮酸乙酯(4b)和蒎酮酸正戊酯(4f)对白纹伊蚊表现出较好的驱避活性,在200 mg/mL浓度时对白纹伊蚊的驱避时间达到2.5 ~ 3.0 h;(2, 2-二甲基-3-乙基环丁基)乙酸与取代苯胺生成的酰基硫脲表现出较好的杀虫活性,其中1-[2-(3-乙基-2, 2-二甲基环丁基)乙酰基]-3-(2-甲基苯基)硫脲(6b)、1-[2-(3-乙基-2, 2-二甲基环丁基)乙酰基]-3-(4-三氟甲基苯基)硫脲(6h)、1-[2-(3-乙基-2, 2-二甲基环丁基)乙酰基]-3-(2-氯苯基)硫脲(6i)、1-[2-(3-乙基-2, 2-二甲基环丁基)乙酰基]-3-(4-氯苯基)硫脲(6j)的杀虫活性较好,在1 g/kg浓度下对亚洲玉米螟的校正死亡率在93.1%以上。因此,蒎酮酸酯和酰基硫脲化合物具有进一步开发研究用以筛选新型驱避剂和杀虫剂的应用价值。
Molecular modification of natural resources materials with unique and novel structure to produce bioacitive compounds is an impotant direction of natural product research. There is abundant resource of turpentine in China, the major component of which isα-pinene.α-Pinene has been widely used as raw material for the production of some compounds necessary for national economy due to its abundant availability, low cost and active configuration.
Sixty two compounds with six kinds were synthesized from 2-(3-acetyl-2, 2-dimethylcyclobutyl)acetic acid (pinonic acid) which was obtained from the oxidation ofα-pinene. Among them 45 compounds were synthesized for the first time. Their structures were characterized by IR, MS, 1H NMR and X-ray diffraction. The antibacterial, repellent and insecticidal activities of the synthetic derivatives were studies in this paper. The structure activity relationships were also studied. This work might lay a solid foundation for further research of new bioacitive compounds.
Pinonic acid was synthesized usingα-pinene as raw material, potassium permanganate as oxidant, ammonium sulfate as pH regulator and water as reaction medium. Then 38 compounds of amides,α,β-unsaturated carbonyl compounds, esters and acylthioureas were synthesized through acylation, aldol condensation, esterification, nucleophilic substitution, nucleophilic addition reactions and so on. Among them 22 compounds were synthesized for the first time. The single crystals of three pinonamides were obtained and their crystal structures were analysed. The cyclobutane fragment of the products was not flat and was flexed as though folded from the dimethylsubstituted C atom to the unsubstituted C atom. The conformation of the cyclobutane represented semi-chair.
Thirteen acylthioureas were obtained through acylchlorination, nucleophilic substitution, nucleophilic addition reaction from (2, 2-dimethyl-3-ethylcyclobutyl)acetic acid which was obtained from pinonic acid via Wolff-Kishner reaction. The single crystals of three acylthioureas were obtained and their crystal structures were analysed.
Eleven new diacylthioureas were obtained through acylchlorination, nucleophilic substitution, nucleophilic addition reaction from 2, 2-dimethylcyclobutyl-1, 3-diacetic acid (sym-homopinic acid) which was obtained from pinonic acid via Willgerodt reaction.
The insecticidal activities of three acylthioureas against Bemisia tabaci were test by medicament spraying method. The insecticidal activities of 37 products with six kinds against Ostrinia furnacalis were tested by artificial diet method. The repellent activities of eight kinds of pinonamides against Musca domestica were tested at the concentration of 100 mg/mL by dipped filter paper mathod. The repellent activities of eight kinds of pinonamides against Monomorium pharaonis were tested at the concentration of 100 mg/mL by dipped seeds method. The repellent activities of eight esters and twelve acylthioureas against Aedes albopictus were tested at the concentration of 100 mg/mL. The antibacterial acitivities of 15 pinonamides and 9α,β-unsaturated carbonyl compounds against Clostridium perfringens, Salmonella typhi, K. peneumoniae, P. aeruginosa, E. coli, Staph. Epidermidis and Staph. aureus were tested by minimum inhibitory concentration method.
Methyl ester, ethyl ester and pentyl ester of pinonic acid have higher repellent activities against Aedes albopictus. The repellent time of them are up to 2.5 ~ 3.0 h at the concentration of 200 mg/mL. The acylthioureas obtained from (2, 2-dimethylcyclobutyl)acetic acid have better insecticidal activities against Ostrinia furnacalis. Among these acylthioureas the insecticidal acitivities of 1-[2-(3-ethyl-2, 2-dimethylcyclobutyl)acetyl]-3-o-tolylthiourea (6b), 1-[2-(3-ethyl-2, 2-dimethylcyclobutyl)acetyl]-3-(4-trifluoromethylphenyl)thiourea (6h), 1-[2-(3-ethyl-2, 2-dimethylcyclobutyl)acetyl]-3-(2-chlorophenyl)thiourea (6i), 1-[2-(3-ethyl-2, 2-dimethylcyclobutyl)acetyl]-3-(4-chlorophenyl)thiourea (6j) are better than that of other compounds. So esters and acylthioureas derivatives of pinonic acid have potential for further research to explore new repellants and insecticides.
引文
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