N-葡萄糖基硫代氨基甲酸酯的合成、生物活性及潜在解毒作用研究
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摘要
硫代氨基甲酸酯是一类具有广泛生物活性的化合物,常被用作杀虫剂、杀菌剂和除草剂。自从1864年Jobst和Hesse从毒扁豆中发现天然存在的氨基甲酸酯(Carbamate)类化合物,人们合成了大量的氨基甲酸酯及硫代氨基甲酸酯类化合物,但大部分都是N-烷基和N-苯基取代衍生物,很少有N-糖基取代衍生物。为了筛选具有生物活性的化合物,我们设计合成了一系列的N-葡萄糖基硫代氨基甲酸酯,进行了杀虫、杀菌和除草活性的测定,并进一步研究了该类化合物在重金属解毒方面的潜在功效。
本文首先研究了N-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)硫代氨基甲酸酯的合成。以D-葡萄糖为初始原料,经过乙酰化、溴化得到乙酰化溴代葡萄糖,然后与硫氰酸铅反应生成相应的葡萄糖基异硫氰酸酯,最后分别与一元醇、二元醇及丙酮肟反应,得到20个N-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)硫代氨基甲酸酯,并用红外光谱、氢核磁共振、碳核磁共振及元素分析确证了化合物的结构。
分别采用浸叶法、菌丝生长速率法及平皿法对20个N-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)硫代氨基甲酸酯进行了杀虫、杀菌和除草活性初筛。结果表明,此类化合物无杀虫、除草活性,但表现出一定的杀菌活性,并发现在一元脂肪醇合成的硫代氨基甲酸酯中,醇部位含奇数个碳原子的杀菌活性比含偶数个碳原子的活性高,二元醇合成的硫代氨基甲酸酯的杀菌活性比一元醇的高。
本文还同时进行了N-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖)硫代氨基甲酸酯与汞离子的亲和能力研究。以N-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖)硫代氨基甲酸酯与Hg2+反应,合成了9种二[O-烷基N-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖)硫代氨基甲酸酯]汞,收率均在80%以上。实验表明,N-葡萄糖基氨基硫代甲酸酯与Hg2+有很强的亲和能力,具有解毒重金属汞的潜在功效。
Thiocarbamates are remarkable of their biological activities and widely used as fungicides, pesticides and herbicides. A lot of carbamates and thiocarbamates were synthesized since natural carbamate compounds were found from physostigmine by Jobst and Hesse in 1864. However, many of the reported thiocarbamates were N-alkyl and N-phenyl or benzyl compounds, few of which were N-glucosyl. In order to find more biologically active compounds, a series of N-(2,3,4,6-tetra-0-acetyl-β-D-glucopyranosyl) thiocarbamates were designed and synthesized. Biological activities of the title compounds, including insecticidal, antifungal and herbicidal activities, were evaluated preliminarily, some of which exhibited antifungal activities. Furthermore the heavy metal potential detoxification of the title compounds was studied.
Firstly, the synthesis of the N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamates was researched. Glucopyranosyl isothiocyanate were prepared by acetylated glucosyl bromine, which was synthesized by D-glucose as the initial raw material after acetylation and bromation, reaction with plumbum thiocyanate. Then twenty N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamates were synthesized by glucopyranosyl isothiocyanate reaction with monohydric, dihydric alcohols and acetone oxime, respectively. The structures of compounds were confirmed by IR,1H NMR,13C NMR and elemental analysis.
Biological activities, including insecticidal, antifungal and herbicidal activities, of the 20 N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamates were evaluated. The results showed that the title compounds have no insecticidal and herbicidal activities, but some of them exhibited certain antifungal activities. It is interesting that there might be certain relationship between antifungal activities and the number of carbon atoms in alcohol position of such compounds synthesized by straight-chain fatty alcohols, i.e., compounds with odd- numbered carbon atoms have stronger antifungal activities than compounds with even-numbered carbon atoms. Furthermore the antifungal activities of bisthiocarbamates are a bit stronger than that of monothiocarbamates.
At the same time, the affinity between thiocarbamates and mercury was studied. Nine bis[O-alkyl N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamato]mercury were synthesized by the reaction of N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamates and mercury with yields over 80%. This strong affinity between thiocarbamates and mercury showed their potential properties in medical or marine environmental detoxification.
本文首先研究了N-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)硫代氨基甲酸酯的合成。以D-葡萄糖为初始原料,经过乙酰化、溴化得到乙酰化溴代葡萄糖,然后与硫氰酸铅反应生成相应的葡萄糖基异硫氰酸酯,最后分别与一元醇、二元醇及丙酮肟反应,得到20个N-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)硫代氨基甲酸酯,并用红外光谱、氢核磁共振、碳核磁共振及元素分析确证了化合物的结构。
分别采用浸叶法、菌丝生长速率法及平皿法对20个N-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)硫代氨基甲酸酯进行了杀虫、杀菌和除草活性初筛。结果表明,此类化合物无杀虫、除草活性,但表现出一定的杀菌活性,并发现在一元脂肪醇合成的硫代氨基甲酸酯中,醇部位含奇数个碳原子的杀菌活性比含偶数个碳原子的活性高,二元醇合成的硫代氨基甲酸酯的杀菌活性比一元醇的高。
本文还同时进行了N-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖)硫代氨基甲酸酯与汞离子的亲和能力研究。以N-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖)硫代氨基甲酸酯与Hg2+反应,合成了9种二[O-烷基N-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖)硫代氨基甲酸酯]汞,收率均在80%以上。实验表明,N-葡萄糖基氨基硫代甲酸酯与Hg2+有很强的亲和能力,具有解毒重金属汞的潜在功效。
Thiocarbamates are remarkable of their biological activities and widely used as fungicides, pesticides and herbicides. A lot of carbamates and thiocarbamates were synthesized since natural carbamate compounds were found from physostigmine by Jobst and Hesse in 1864. However, many of the reported thiocarbamates were N-alkyl and N-phenyl or benzyl compounds, few of which were N-glucosyl. In order to find more biologically active compounds, a series of N-(2,3,4,6-tetra-0-acetyl-β-D-glucopyranosyl) thiocarbamates were designed and synthesized. Biological activities of the title compounds, including insecticidal, antifungal and herbicidal activities, were evaluated preliminarily, some of which exhibited antifungal activities. Furthermore the heavy metal potential detoxification of the title compounds was studied.
Firstly, the synthesis of the N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamates was researched. Glucopyranosyl isothiocyanate were prepared by acetylated glucosyl bromine, which was synthesized by D-glucose as the initial raw material after acetylation and bromation, reaction with plumbum thiocyanate. Then twenty N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamates were synthesized by glucopyranosyl isothiocyanate reaction with monohydric, dihydric alcohols and acetone oxime, respectively. The structures of compounds were confirmed by IR,1H NMR,13C NMR and elemental analysis.
Biological activities, including insecticidal, antifungal and herbicidal activities, of the 20 N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamates were evaluated. The results showed that the title compounds have no insecticidal and herbicidal activities, but some of them exhibited certain antifungal activities. It is interesting that there might be certain relationship between antifungal activities and the number of carbon atoms in alcohol position of such compounds synthesized by straight-chain fatty alcohols, i.e., compounds with odd- numbered carbon atoms have stronger antifungal activities than compounds with even-numbered carbon atoms. Furthermore the antifungal activities of bisthiocarbamates are a bit stronger than that of monothiocarbamates.
At the same time, the affinity between thiocarbamates and mercury was studied. Nine bis[O-alkyl N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamato]mercury were synthesized by the reaction of N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamates and mercury with yields over 80%. This strong affinity between thiocarbamates and mercury showed their potential properties in medical or marine environmental detoxification.
引文
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