【作者】 王子云；

【导师】 汪焱钢；

【作者基本信息】 华中师范大学 ， 有机化学， 2005， 硕士

【摘要】 植物生长调节剂是人工合成的具有植物激素活性的物质,为了寻找并筛选具有较高植物生长调节活性的物质,本文利用生物等排原理和亚结构连接法,对噻二唑的母体进行修饰,设计并合成了61个新的化合物。 通过文献检索,对植物生长调节剂的发展进行了系统的论述,对1,3,4-噻二唑类化合物、酰基硫脲类化合物的生物活性及合成方法,进行了比较全面的综述。利用酰基异硫氰酸酯与氨基杂环在无水非质子溶剂中发生亲核加成反应,合成三个系列的目标化合物(Ⅰ、Ⅱ、Ⅲ)。利用2.氨基-5-对三氟甲基苯基-1,3,4-噻二唑和2-氨基-5-(1-邻氯苯氧乙基)-1,3,4-噻二唑分别与芳酰基异硫氰酸酯或芳氧乙酰基异硫氰酸酯在无水乙腈中反应,制得系列(Ⅰ)共24个和系列(Ⅱ)共22个新芳酰基硫脲/芳氧乙酰基硫脲化合物;同时利用5-氨基-1,3,4-噻二唑-2-羧酸与芳酰基异硫氰酸酯或芳氧乙酰基异硫氰酸酯在无水乙腈中反应,制得系列(Ⅲ)共15个芳酰基硫脲/芳氧乙酰基硫脲新化合物。目标化合物的组成和结构经IR、MS、~1H NMR和元素分析加以确证。对目标化合物的理化性质、波谱数据和合成条件进行了系统的讨论。61个目标化合物的结构如下:Ⅰ.N-(5-对三氟甲基苯基-1,3,4-噻二唑-2-基)-N’-芳酰基硫脲/芳氧乙酰基硫脲Ⅱ.N-[5-(1-邻氯苯氧乙基)-1,3,4-噻二唑-2-基]-N’-芳酰基硫脲/芳氧乙酰基硫脲Ⅲ.N-(2-羧基-1,3,4-噻二唑-5-基)-N’-芳酰基硫脲/芳氧乙酰基硫脲 采用小麦芽鞘法和黄瓜子叶扩张法对目标化合物的植物生长调节活性进行了初步测试,生测结果表明,三个系列化合物均表现了一定的生长素活性和细胞分(?)活性。其细胞分裂素活性比激动素差,而生长素活性Ie、Ig、Im、Ip、Iq、I(?)、Ⅱc、Ⅱd、Ⅱe、Ⅲc、Ⅲd、Ⅲn接近或略超过β-吲哚乙酸。更多还原

【Abstract】 Plant growth regulator is a kind of organic compound with plant hormone function synthesized by artificial methods.In order to seek good plant growth regulators, we have modified the main structure of 1,3,4-thiadiazole and synthesisized 61 new compouds by Bioisosterism Principles and Substructure Link Wory.By consulting concerning literatures, we reviewed the biological activities and the synthesis methods of 1,3,4-thiadiazoles, acyl thioureas. Target compounds (Ⅰ、Ⅱ、Ⅲ) are synthesized by nucleophilic addition of amino heterocycle with acyl isothiocyanates in anhydrous and aprotonic solvent.Reaction of 2-amino-5-(p-trifluoromethyl phenyl)-1,3,4- thiadiazole and 2-amino-5-(1-o-chlorophenoxyethyl)-l,3,4-thiodiazole with aroyl or aryloxyacetyl isothiocyanates in anhydrous acetonitrile gave 24(Ⅰ) and 22(Ⅱ)new aroylthioureas orAryloxyacetyl thioureas. At the same time , Reaction of 5-amino-l,3,4-thiodiazole-2- carboxylic acid with aroyl isothiocyanates or aryloxyacetyl isothiocyanates in anhydrous acetonitrile gave 15(Ⅲ) new aroylthioureas or Aryloxyacetyl thioureas. IR、 MS、 ~1H NMR and elementary analysis comfirm their structure, their physical-chemical properties and spectrum data and synthesis condition of the target compounds were reported firstly. The main structures of the target compounds were as follows:Ⅰ. N-[5-(p-trifluoromethyl phenyl)-l,3,4-thiadiazol-2-yl]-N’-aroyl throurea/ aryloxyacetyl thioureaⅡ. N-[5-(1-o-chlorophenoxyethyl)-1,3,4-thiadiazol-2-yl ]-N’- aroyl throurea/ aryloxyacetyl throureaⅢ. N-( 2-carboxyl-1,3,4-thiodiazol-5-yl) -N’- aroyl thiourea / aryloxyacetyl thioureaThe plant growth regulating activity was tested by taking root and wheat sheath on the target compounds and the cucumber cotyledon expansion, preliminary results indicated that many of acyl thioureas exhibited higher auxin and cytokinin activity. The cytokinin activity of all compounds was lower than that of 6-furylmethyl purine. However, The auxin activity of Ie* Ig, Im* Ip* Iq, h\ He, lid, IIe> Me, Hid* III n was weekly higher than that of 6-indolyl acetic acid.更多还原