含氮杂环化合物的设计合成
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摘要
探索杂环化合物的合成及生物活性是有机化学中最具生命力的研究课题之一。含氮类杂环化合物，如三唑、噻二唑、吡唑、噁二唑等，具有杀虫、杀菌、除草、抗病毒、消炎、抗肿瘤和杀微生物等生物活性。近几年来，很多研究在该领域开展，但环上取代基的位置及结构对改善药效，降低毒副作用的影响是不可忽略的。因而，深入研究该类(稠)杂环上取代基的变化，对于开发此类(稠)杂环衍生物潜在的生物活性仍具有重要的意义。
在现有众多杂环化合物中，三唑类化合物由于其广泛的生物活性而备受重视，已有许多品种作为杀菌剂、植物生长调节剂和药物得到开发和应用。本论文对三唑类化合物的结构、合成、应用、作用机制、构效关系及生物活性研究进展进行了综述，利用活性亚结构拼接和生物电子等排原理，将不同作用机制的活性基团引入三唑类化合物中，设计合成了四大系列共34个新型三唑类衍生物。
第一部分：利用具有抗菌、杀虫、除草、植物调解等广泛生物活性的1，2，4-三唑为基本原料，分别与水杨醛、水杨醛的衍生物反应，制得席夫碱10种，并用元素分析、红外光谱、核磁共振光谱确定了基本结构，并用X-衍射确定4-水杨醛亚氨基-3烷基-1，2，4-三唑-5硫酮席夫碱的晶体结构。
第二部分：3-烃基-4-氨基-5-巯基均三唑类化合物是众多三唑类化合物中较为重要的一类，具有多种药理活性，如止痛、消炎、杀(抗)菌、除草、杀虫、抗病毒、降血压及植物生长调节活性等。我们采用活性亚结构拼接的方法设计合成了10个含均三唑环的新型三唑类化合物。
第三部分：利用3-三氟甲基-4氨基-5巯基-1，2，4-三唑为原料，分别与具有多种生物活性的2-，3-，4-，吡啶甲酸及α-萘乙酸在POCl_3催化剂下反应，合成了4种3-三氟甲基-6-吡啶基均三唑并[3，4-b]-1，3，4-噻二唑类化合物，并用元素分析、红外光谱、核磁共振等确定了基本结构。在这章的反应过程中对比了常规加热和微波加热对反应的不同影响，发现与常规加热方法相比微波辐射加热条件下的反应时间大为缩短、产率也普遍有所提高。
第四部分：1，3，4-噁二唑及其取代衍生物是一类重要的生理活性物质，我们把1，3，4-噁二唑环和1，2，4-三氮唑环两个活性亚结构结合起来，设计合成了10个含上述两类基本活性结构单元的新型化合物。
Studying on the synthesis of heterocyclic compounds and their biologic activity isone of the most spirited fields in organic chemistry. Heterocyclic compounds liketriazoles, thiadiazoles, pyrazoles,oxadiazoles have showed broad spectrum of biologicalactivities, such as antifungal, anticancer, antiviral, herbicidal. Their relatedcompounds have found useful in medicine, agriculture and industry. But differentsubstituted group in the heterocyclic compound will have great influence on thebioactivity of compounds.
Triazole compounds have been found to show wide spread biological activities,many of them have been developed and used as fungicides, plant growth regulators andmedicine. In this thesis, We have reviewed the recent advances in the studies on thestructures, synthesis, action mechanism, structure-activity relationship and biologicalactivities of triazoles, different active groups of action mechanism were induced into thetriazole compounds according to the concept of bioisosterism. Thirty-four novel triazolecompounds in four big systems were designed and synthesized.
In the first part, ten novel fused heterocyclic compounds Schiff bases have beensynthesized by reaction of 3-alky-4amino-5-mercapto-1,2,4-triazoles with salicyl-aldehyde, 5-nitro salicylaldenhyde, 3-nitro salicylaldenhyde, 5-bromo salicyl- aldenhyde, heliotropine in the of hydrochloric acid at 80℃for 10hr, their structures have beenconfirmed by EA, IR, ~1H NMR, X-ray crystallography analysis.
In second part,3-alkyl-4-amino-5-mercapto-1,2,4-triazole compounds are one ofmany triazole compounds, and have good pharmacology, such as acesodyne、diminishinflammation、sterilization、weeding、pesticide、antivirus、lower blood pressure andplant growth regulating activities etc. Twenty six new triazole compounds containing1,2,4-triazole group have been synthesized through jointing activity substructures.
In third part, four compounds having the structure of 3-trifluoromethy-6-substituted triazolo[3,4-b]-1,3,4-thiadiazoles were synthesized from 3 trifluoromethyl-4-amino-5-mercapto-1,2,4-triazoles with 2-,3-,4-nicotinic acid andα-naphthyaceticacid using phosphorus oxychloride as a catalyst respectively. The structures of thesecompounds were characterized by using EA, IR, ~1H NMR. The reaction heated bytraditional and microwave method was compared in this chapter, Compared with thetraditional synthetic method, under the microwave radiation the same products wereobtained with shorter reaction time and higher yield.
In fourth part 1,3,4-oxadiazole and its derivatives have received increasinginterests in the agrochemical and pharmaceutical fields because of their unique anddiverse biological properties. To get further information about their fungicidal activity,18 new compounds have been synthesized including these two basic activity structuresthrough jointing substructure both 1,3,4-oxadiazole and 1,2,4-triazole.
在现有众多杂环化合物中，三唑类化合物由于其广泛的生物活性而备受重视，已有许多品种作为杀菌剂、植物生长调节剂和药物得到开发和应用。本论文对三唑类化合物的结构、合成、应用、作用机制、构效关系及生物活性研究进展进行了综述，利用活性亚结构拼接和生物电子等排原理，将不同作用机制的活性基团引入三唑类化合物中，设计合成了四大系列共34个新型三唑类衍生物。
第一部分：利用具有抗菌、杀虫、除草、植物调解等广泛生物活性的1，2，4-三唑为基本原料，分别与水杨醛、水杨醛的衍生物反应，制得席夫碱10种，并用元素分析、红外光谱、核磁共振光谱确定了基本结构，并用X-衍射确定4-水杨醛亚氨基-3烷基-1，2，4-三唑-5硫酮席夫碱的晶体结构。
第二部分：3-烃基-4-氨基-5-巯基均三唑类化合物是众多三唑类化合物中较为重要的一类，具有多种药理活性，如止痛、消炎、杀(抗)菌、除草、杀虫、抗病毒、降血压及植物生长调节活性等。我们采用活性亚结构拼接的方法设计合成了10个含均三唑环的新型三唑类化合物。
第三部分：利用3-三氟甲基-4氨基-5巯基-1，2，4-三唑为原料，分别与具有多种生物活性的2-，3-，4-，吡啶甲酸及α-萘乙酸在POCl_3催化剂下反应，合成了4种3-三氟甲基-6-吡啶基均三唑并[3，4-b]-1，3，4-噻二唑类化合物，并用元素分析、红外光谱、核磁共振等确定了基本结构。在这章的反应过程中对比了常规加热和微波加热对反应的不同影响，发现与常规加热方法相比微波辐射加热条件下的反应时间大为缩短、产率也普遍有所提高。
第四部分：1，3，4-噁二唑及其取代衍生物是一类重要的生理活性物质，我们把1，3，4-噁二唑环和1，2，4-三氮唑环两个活性亚结构结合起来，设计合成了10个含上述两类基本活性结构单元的新型化合物。
Studying on the synthesis of heterocyclic compounds and their biologic activity isone of the most spirited fields in organic chemistry. Heterocyclic compounds liketriazoles, thiadiazoles, pyrazoles,oxadiazoles have showed broad spectrum of biologicalactivities, such as antifungal, anticancer, antiviral, herbicidal. Their relatedcompounds have found useful in medicine, agriculture and industry. But differentsubstituted group in the heterocyclic compound will have great influence on thebioactivity of compounds.
Triazole compounds have been found to show wide spread biological activities,many of them have been developed and used as fungicides, plant growth regulators andmedicine. In this thesis, We have reviewed the recent advances in the studies on thestructures, synthesis, action mechanism, structure-activity relationship and biologicalactivities of triazoles, different active groups of action mechanism were induced into thetriazole compounds according to the concept of bioisosterism. Thirty-four novel triazolecompounds in four big systems were designed and synthesized.
In the first part, ten novel fused heterocyclic compounds Schiff bases have beensynthesized by reaction of 3-alky-4amino-5-mercapto-1,2,4-triazoles with salicyl-aldehyde, 5-nitro salicylaldenhyde, 3-nitro salicylaldenhyde, 5-bromo salicyl- aldenhyde, heliotropine in the of hydrochloric acid at 80℃for 10hr, their structures have beenconfirmed by EA, IR, ~1H NMR, X-ray crystallography analysis.
In second part,3-alkyl-4-amino-5-mercapto-1,2,4-triazole compounds are one ofmany triazole compounds, and have good pharmacology, such as acesodyne、diminishinflammation、sterilization、weeding、pesticide、antivirus、lower blood pressure andplant growth regulating activities etc. Twenty six new triazole compounds containing1,2,4-triazole group have been synthesized through jointing activity substructures.
In third part, four compounds having the structure of 3-trifluoromethy-6-substituted triazolo[3,4-b]-1,3,4-thiadiazoles were synthesized from 3 trifluoromethyl-4-amino-5-mercapto-1,2,4-triazoles with 2-,3-,4-nicotinic acid andα-naphthyaceticacid using phosphorus oxychloride as a catalyst respectively. The structures of thesecompounds were characterized by using EA, IR, ~1H NMR. The reaction heated bytraditional and microwave method was compared in this chapter, Compared with thetraditional synthetic method, under the microwave radiation the same products wereobtained with shorter reaction time and higher yield.
In fourth part 1,3,4-oxadiazole and its derivatives have received increasinginterests in the agrochemical and pharmaceutical fields because of their unique anddiverse biological properties. To get further information about their fungicidal activity,18 new compounds have been synthesized including these two basic activity structuresthrough jointing substructure both 1,3,4-oxadiazole and 1,2,4-triazole.
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