新型三唑并嘧啶衍生物的合成及生物活性研究
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摘要
三唑并嘧啶类杂环衍生物往往表现出广泛的生物活性，在医药、农药以及材料等研究领域受到了人们的普遍关注。本文在课题组前期研究工作的基础上，对前期已经发现的具有杀菌和除草活性的几类先导结构开展优化研究，设计合成了五类共216个新型的1，2，4-三唑并[1，5-a]嘧啶类化合物，采用NMR、MS以及元素分析等手段对所合成的化合物进行了系统的结构表征，同时还采用X—射线衍射技术测定了6个代表性化合物的晶体结构。通过对所合成化合物的生物活性测定，结果发现这些化合物并没有表现出所期望的杀菌活性，但部分化合物表现出了良好的除草活性。进一步的酶抑制活性测定结果表明，2-取代苯氧基-1，2，4-三唑并[1，5-a]嘧啶类化合物对乙酰乳酸合成酶表现出较好的抑制活性，对部分表现出较高除草活性的代表性化合物的作物安全性试验结果表明，该类化合物具有良好的作物安全性，显示出良好的进一步研究价值。此外，在合成目标化合物的过程中，我们首次发现了1，2，4-三唑并[1，5-a]嘧啶类化合物的碱催化肼解开环反应，并发展了一种三组分一锅煮构筑三唑并嘧啶类杂环体系的新方法。具体研究内容主要包括以下四个方面：
1、设计合成了五类共216个新型的1，2，4-三唑并[1，5-a]嘧啶类化合物，采用NMR、MS、元素分析对所合成的化合物进行了系统的结构表征，同时还测定了6个代表性化合物的晶体结构。
2、首次发现了1，2，4-三唑并[1，5-a]嘧啶类化合物的碱催化肼解开环反应，系统研究了开环反应的取代基效应以及微波辐射、pH值、水合肼用量对开环反应的影响。并提出了反应可能的机理。
3、利用电子等排取代原理，将3—氨基—5—取代—1，2，4-三唑取代传统Biginelli反应的(硫)脲组分，发展了一种三组分一锅煮构筑三唑并嘧啶杂环的新方法。通过对反应溶剂、催化剂、微波辐射等条件的优化，最终发现在乙醇溶剂中、无需催化剂、150℃微波辐射30分钟就可以得到比较理想的结果，反应表现出较好的区域选择性，并以中等的分离收率得到产物。此外，我们通过~1HNMR、~(13)CNMR、MS以及X—射线晶体衍射技术确证了产物的结构，提出了可能的反应机理。
4、对所合成的化合物进行了系统的生物活性筛选，结果表明：所合成的化合物没有表现出理想的杀菌活性，但部分化合物表现出了良好的除草活性。进一步的酶活性测试和作物安全性试验结果表明，部分化合物对乙酰乳酸合成酶表现出较高的抑制活性和作物安全性，显示出良好的进一步研究价值。
Triazolopyrimidine derivatives have been found to show widespread biological activities, many of which have been developed as fungicide, herbicide, medicine and functional material. In order to optimize the fungicidal and herbicidal lead compounds discovered previously by our research group, 216 novel 1, 2, 4-triazolo[1,5-a]pyrimidine derivatives were designed and synthesized, whose structures were characterized by NMR, MS spectrum and elemental analysis. The crystal structures of six representative compounds were determined by X-ray refraction analysis. In addition, a novel base-catalytic hydrazinolysis ring-opening reaction of triazolopyrimidines was discovered, and the effects of substituent, pH value and amount of hydrazine hydrate on the ring-opening reaction were studied systematically. And we propose a mechanism for ring opening reaction of triazolopyrimidines. Further, a one-pot three component Biginelli reaction for the synthesis of triazolopyrimidine was designed based on the principle of isoelectronic substitution. Bioassay indicated that most of compounds did not exhibit good fungicidal activities, however, some target compounds displayed promising herbicidal activities and ALS-inhibiting activities. The further crop safety experiment indicated the representative compounds displayed excellent selectivity between crop and weeds, which showed the potential value of these compounds for further study. What the paper studied may be summarized as follows:
1 216 novel 1,2,4-triazolo[1,5-a]pyrimidine derivatives were designed and synthesized, whose structures were characterized by NMR, MS spectrum and elemental analysis. The crystal structures of six representative compounds were determined by X-ray refraction analysis.
2, A novel base-catalytic hydrazinolysis ring-opening reaction of triazolopyrimidines was discovered, and the effects of substituent, pH value and amount of hydrazine hydrate on the ring-opening reaction were studied systematically. And we propose a mechanism for ring opening
reaction of triazolopyrimidines.
3、A one-pot three component Biginelli reaction for the synthesis of triazolopyrimidine was designed based on the principle of isoelectronic substitution. We optimized solvent and catalyst of the ring opening reaction, found ethanol was the best solvent. Finally, we obtained moderate yield and better regionselectivity under microwave irradiation (with temperature 150℃and reaction time 30 min), The structures of product were characterized by NMR, MS spectrum, elemental analysis and X-ray diffraction. We deduce the possible reaction mechanism.
4、Bioassay indicated that most of compounds did not exhibit good fungicidal activities, however, some target compounds displayed promising herbicidal activities and ALS-inhibiting activities. The further crop safety experiment indicated the representative compounds displayed excellent selectivity between crop and weeds, which showed the potential value of these compounds for further study. Key words: lead compound, 1, 2, 4-triazolo[1,5-a]pyrimidine, microwave assisted organic synthesis, hydrazinolysis ring-opening reaction, Biginelli reaction, fungicidal activity, herbicidal activity.
1、设计合成了五类共216个新型的1，2，4-三唑并[1，5-a]嘧啶类化合物，采用NMR、MS、元素分析对所合成的化合物进行了系统的结构表征，同时还测定了6个代表性化合物的晶体结构。
2、首次发现了1，2，4-三唑并[1，5-a]嘧啶类化合物的碱催化肼解开环反应，系统研究了开环反应的取代基效应以及微波辐射、pH值、水合肼用量对开环反应的影响。并提出了反应可能的机理。
3、利用电子等排取代原理，将3—氨基—5—取代—1，2，4-三唑取代传统Biginelli反应的(硫)脲组分，发展了一种三组分一锅煮构筑三唑并嘧啶杂环的新方法。通过对反应溶剂、催化剂、微波辐射等条件的优化，最终发现在乙醇溶剂中、无需催化剂、150℃微波辐射30分钟就可以得到比较理想的结果，反应表现出较好的区域选择性，并以中等的分离收率得到产物。此外，我们通过~1HNMR、~(13)CNMR、MS以及X—射线晶体衍射技术确证了产物的结构，提出了可能的反应机理。
4、对所合成的化合物进行了系统的生物活性筛选，结果表明：所合成的化合物没有表现出理想的杀菌活性，但部分化合物表现出了良好的除草活性。进一步的酶活性测试和作物安全性试验结果表明，部分化合物对乙酰乳酸合成酶表现出较高的抑制活性和作物安全性，显示出良好的进一步研究价值。
Triazolopyrimidine derivatives have been found to show widespread biological activities, many of which have been developed as fungicide, herbicide, medicine and functional material. In order to optimize the fungicidal and herbicidal lead compounds discovered previously by our research group, 216 novel 1, 2, 4-triazolo[1,5-a]pyrimidine derivatives were designed and synthesized, whose structures were characterized by NMR, MS spectrum and elemental analysis. The crystal structures of six representative compounds were determined by X-ray refraction analysis. In addition, a novel base-catalytic hydrazinolysis ring-opening reaction of triazolopyrimidines was discovered, and the effects of substituent, pH value and amount of hydrazine hydrate on the ring-opening reaction were studied systematically. And we propose a mechanism for ring opening reaction of triazolopyrimidines. Further, a one-pot three component Biginelli reaction for the synthesis of triazolopyrimidine was designed based on the principle of isoelectronic substitution. Bioassay indicated that most of compounds did not exhibit good fungicidal activities, however, some target compounds displayed promising herbicidal activities and ALS-inhibiting activities. The further crop safety experiment indicated the representative compounds displayed excellent selectivity between crop and weeds, which showed the potential value of these compounds for further study. What the paper studied may be summarized as follows:
1 216 novel 1,2,4-triazolo[1,5-a]pyrimidine derivatives were designed and synthesized, whose structures were characterized by NMR, MS spectrum and elemental analysis. The crystal structures of six representative compounds were determined by X-ray refraction analysis.
2, A novel base-catalytic hydrazinolysis ring-opening reaction of triazolopyrimidines was discovered, and the effects of substituent, pH value and amount of hydrazine hydrate on the ring-opening reaction were studied systematically. And we propose a mechanism for ring opening
reaction of triazolopyrimidines.
3、A one-pot three component Biginelli reaction for the synthesis of triazolopyrimidine was designed based on the principle of isoelectronic substitution. We optimized solvent and catalyst of the ring opening reaction, found ethanol was the best solvent. Finally, we obtained moderate yield and better regionselectivity under microwave irradiation (with temperature 150℃and reaction time 30 min), The structures of product were characterized by NMR, MS spectrum, elemental analysis and X-ray diffraction. We deduce the possible reaction mechanism.
4、Bioassay indicated that most of compounds did not exhibit good fungicidal activities, however, some target compounds displayed promising herbicidal activities and ALS-inhibiting activities. The further crop safety experiment indicated the representative compounds displayed excellent selectivity between crop and weeds, which showed the potential value of these compounds for further study. Key words: lead compound, 1, 2, 4-triazolo[1,5-a]pyrimidine, microwave assisted organic synthesis, hydrazinolysis ring-opening reaction, Biginelli reaction, fungicidal activity, herbicidal activity.
引文
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