微波辐射下含取代苯并咪唑基噻二嗪、酰氨基硫脲、噻二唑衍生物的合成
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摘要
自1969年,美国科学家Vanderhoff首次将微波辐射技术应用于有机反应后,微波在有机合成中的应用发展极为迅速。其特点是能在极短的时间内迅速加热反应底物,这种加热方式可以完全有可能使一些在常规回流条件下不能被活化而无法进行或难以进行的反应得以发生。因此微波技术在化学各分支及医药、环保等领域都有着广阔的应用前景。
苯并咪唑类化合物具有杀菌、杀虫、抗病毒、抗肿瘤及治疗溃疡、降压等生物活性,而备受关注。在自然界中,苯并咪唑作为许多酶的活性中心功能基,参与了许多重要的生物化学反应,对生命活动起着十分重要的作用。1,2,4-三唑[3,4-b]-1',3',4'-噻二嗪、酰氨基硫脲、1,3,4-噻二唑杂环化合物也表现出消炎、止痛、抗菌、抑制微生物、抗病毒、调节植物生长等广谱的生物活性,因而受到人们的广泛关注。
根据活性叠加原理,我们将苯并咪唑基团引入到噻二嗪、酰氨基硫脲、噻二唑衍生物中,合成出未见文献报道的一系列结构新颖的含苯并咪唑基的噻二嗪、酰氨基硫脲、1,3,4-噻二唑衍生物,以期实现多种生物活性的叠加,为后期活性化合物的筛选工作提供了丰富的物质来源。
本论文的主要分以下两部分:
第一.文献综述部分。对微波辐射的原理及其在有机反应中的应用,苯并咪唑、噻二嗪、酰氨基硫脲、噻二唑衍生物的研究进展及生物活性进行了较为系统的阐述。
第二.实验部分。主要工作分为三部分:
1.分别采用微波辐射法和常规方法,将3-(2-取代苯并咪唑-1-亚甲基)-4-氨基-5-巯基-1,2,4-三唑与α-溴代芳基乙酮反应,合成了一系列未见文献报道的1,2,4-三唑[3,4-b]-1',3',4'-噻二嗪类化合物,并对实验结果进行了讨论;
2.分别在微波辐射法和常规方法下,芳酰基异硫氰酸酯与1-(2-三氟甲基苯并咪唑-1-基)乙酰肼反应生成了一系列未见文献报道的1-(2-三氟甲基苯并咪唑-1-乙酰基)-4-芳酰基氨基硫脲,并对合成的化合物进行了初步的生物活性测试;
3.以在微波辐射下合成的1-(2-三氟甲基苯并咪唑-1-乙酰基)-4-芳酰基氨基硫脲再在微波辐射下合环得到了一系列的2-芳甲酰氨基-5-(2-三氟甲基-苯并咪唑-1-亚甲基)-1,3,4-噻二唑,并对实验结果进行了讨论。
本论文的创新之处:
1.采用微波辐射法合成的3-(2-甲基苯并咪唑-1-亚甲基)-6-芳基-7H-1',2',4'-三唑[3,4-b]-1",3",4"-噻二嗪和3-(2-三氟甲基苯并咪唑-1-亚甲基)-6-芳基-7H-1',2',4'-三唑[3,4-b]-1",3",4"-噻二嗪未见文献报道,并对微波实验的条件进行了讨论;
2.微波辐射下合成了一系列未见文献报道的1-(2-三氟甲基苯并咪唑-1-乙酰基)-4-芳酰基氨基硫脲,化合物的初步生物活性测试表明2a具有一定的抗HIV-1逆转录酶活性;
3.以在微波辐射下合成的前体化合物再在微波辐射下反应得到10个2-芳甲酰氨基-5-(2-三氟甲基-苯并咪唑-1-亚甲基)-1,3,4-噻二唑,经过两步的微波反应,产物纯度较高。
The application of microwave irradiation in organic synthesis develope very fast, since 1969, the first time the microwave irradiation technology used in organic reactions by American scientist Vanderhoff. The characteristic of microwave irradiation is that it can heating reaction substrates in a very short time, this heating method can make these reactions which can not proceed on conventional heating processes taking place. Microwave technology has a wide application prospect in all branches of chemistry, biotechnology and environmental protection.
Benzimidazole moiety displays a broad spectrum of biological activities including antiviral, antifungicide, anti-inflammatory effects, some benzimidazole compounds have found applications in diverse therapeutic areas for hypertension and ulcer. As an active center functional group of some enzymes, benzimidazole scaffold takes part in many signficant biochemical processes and paly an important role in biological activities. 1,2,4-triazolo[3,4-b]-1',3',4'-thiadiazine, thiosemicarbazide, 1,3,4-thiadiazole heterocyclic compounds also exhibits high biological activities, such as anti-inflammatory, analgesic, antibacterial, inhibit microorganism, antiviral and regulation of plant growth.
In order to realize combination of multiform active ingredients, we designed and have synthesized a series of novel thiadiazine, thiosemicarbazide and 1,3,4-thiadiazole derivatives which containing benzimidazole compounds in order to enhance their biological activities. It extended the research field of such compounds and provided abundant leading compounds for later selecting work of effective drugs.
This thesis consists of two major parts:
The first part is about literature review. The progress in application and synthesis of benzoimidazole, thiadiazine, thiosemicarbazide, thiadiazole derivatives and the principle of microwave irradiation and it’s application in organic reactions were systematic exposition.
The second part is about experimental content. Major work as follows:
1. A series of novel 1,2,4-triazolo[3,4-b]- 1',3',4'-thiadiazine derivatives were synthesized by the reaction of 3-(2-substituted benzoimidazole-1-methylene)-4-amino-5-mercapto-1,2, 4-triazole withα-bromoacetophenones under microwave irradiation and heating. Comparison of the conventional refluxing method and microwave irradiation accelerate means, discussed for the results;
2. A series of novel 1-(2-trifluoromethylbenzimidazol-1-acetyl)-4-aroylthiosemicarbazide were synthesized by the reaction of 1-(2-trifluoromethylbenzimidazole-1-yl)acetyl hydrazine with aroylisothiocyanate under microwave irradiation and heating.The preliminary biological activity of the target compounds have been tested;
3. 1-(2-trifluoromethylbenzimidazol-1-acetyl)-4-aroylthiosemicarbazide were synthesized under microwave irradiation. Then compounds were cyclized in acetic acid to afford a series of novel 2-aroylamino-5-(2-trifluoromethylbenzimidazol-1-ylmethyl)-1,3,4-thiadi- azole in excellent yields under microwave irradiation. Comparison of the conventional refluxing method and microwave irradiation accelerate means, discussed for the results.
The innovations of the paper are based on the follow:
1. 3-(2-methyl benzoimidazole-1-methylene)-6-aryl-7H-1',2',4'-triazolo[3,4-b]-1",3",4"- thiadiazine and 3-(2-trifluoromethyl benzoimidazole-1-methylene)-6-aryl-7H-1',2',4' -triazolo[3,4-b]-1",3",4"-thiadiazine were synthesized unreported in the literatures under microwave irradiation. The conditions of microwave irradiation were discussed;
2. A series of novel 1-(2-trifluoromethylbenzimidazol-1-acetyl)-4-aroylthio-semicarbazide were synthesized under microwave irradiation. The preliminary biological activity of the target compounds have been tested, the result show that compound 2a have some anti-HIV-1 reverse transcriptase activity;
3. Ten 2-aroylamino-5-(2-trifluoromethyl-benzimidazol-1-ylmethyl)-1,3,4-thiadiazole were synthesized under microwave irradiation, ten precursor compounds were synthesized under microwave irradiation too. After two steps of the microwave irradiation, high purity products were obtained.
苯并咪唑类化合物具有杀菌、杀虫、抗病毒、抗肿瘤及治疗溃疡、降压等生物活性,而备受关注。在自然界中,苯并咪唑作为许多酶的活性中心功能基,参与了许多重要的生物化学反应,对生命活动起着十分重要的作用。1,2,4-三唑[3,4-b]-1',3',4'-噻二嗪、酰氨基硫脲、1,3,4-噻二唑杂环化合物也表现出消炎、止痛、抗菌、抑制微生物、抗病毒、调节植物生长等广谱的生物活性,因而受到人们的广泛关注。
根据活性叠加原理,我们将苯并咪唑基团引入到噻二嗪、酰氨基硫脲、噻二唑衍生物中,合成出未见文献报道的一系列结构新颖的含苯并咪唑基的噻二嗪、酰氨基硫脲、1,3,4-噻二唑衍生物,以期实现多种生物活性的叠加,为后期活性化合物的筛选工作提供了丰富的物质来源。
本论文的主要分以下两部分:
第一.文献综述部分。对微波辐射的原理及其在有机反应中的应用,苯并咪唑、噻二嗪、酰氨基硫脲、噻二唑衍生物的研究进展及生物活性进行了较为系统的阐述。
第二.实验部分。主要工作分为三部分:
1.分别采用微波辐射法和常规方法,将3-(2-取代苯并咪唑-1-亚甲基)-4-氨基-5-巯基-1,2,4-三唑与α-溴代芳基乙酮反应,合成了一系列未见文献报道的1,2,4-三唑[3,4-b]-1',3',4'-噻二嗪类化合物,并对实验结果进行了讨论;
2.分别在微波辐射法和常规方法下,芳酰基异硫氰酸酯与1-(2-三氟甲基苯并咪唑-1-基)乙酰肼反应生成了一系列未见文献报道的1-(2-三氟甲基苯并咪唑-1-乙酰基)-4-芳酰基氨基硫脲,并对合成的化合物进行了初步的生物活性测试;
3.以在微波辐射下合成的1-(2-三氟甲基苯并咪唑-1-乙酰基)-4-芳酰基氨基硫脲再在微波辐射下合环得到了一系列的2-芳甲酰氨基-5-(2-三氟甲基-苯并咪唑-1-亚甲基)-1,3,4-噻二唑,并对实验结果进行了讨论。
本论文的创新之处:
1.采用微波辐射法合成的3-(2-甲基苯并咪唑-1-亚甲基)-6-芳基-7H-1',2',4'-三唑[3,4-b]-1",3",4"-噻二嗪和3-(2-三氟甲基苯并咪唑-1-亚甲基)-6-芳基-7H-1',2',4'-三唑[3,4-b]-1",3",4"-噻二嗪未见文献报道,并对微波实验的条件进行了讨论;
2.微波辐射下合成了一系列未见文献报道的1-(2-三氟甲基苯并咪唑-1-乙酰基)-4-芳酰基氨基硫脲,化合物的初步生物活性测试表明2a具有一定的抗HIV-1逆转录酶活性;
3.以在微波辐射下合成的前体化合物再在微波辐射下反应得到10个2-芳甲酰氨基-5-(2-三氟甲基-苯并咪唑-1-亚甲基)-1,3,4-噻二唑,经过两步的微波反应,产物纯度较高。
The application of microwave irradiation in organic synthesis develope very fast, since 1969, the first time the microwave irradiation technology used in organic reactions by American scientist Vanderhoff. The characteristic of microwave irradiation is that it can heating reaction substrates in a very short time, this heating method can make these reactions which can not proceed on conventional heating processes taking place. Microwave technology has a wide application prospect in all branches of chemistry, biotechnology and environmental protection.
Benzimidazole moiety displays a broad spectrum of biological activities including antiviral, antifungicide, anti-inflammatory effects, some benzimidazole compounds have found applications in diverse therapeutic areas for hypertension and ulcer. As an active center functional group of some enzymes, benzimidazole scaffold takes part in many signficant biochemical processes and paly an important role in biological activities. 1,2,4-triazolo[3,4-b]-1',3',4'-thiadiazine, thiosemicarbazide, 1,3,4-thiadiazole heterocyclic compounds also exhibits high biological activities, such as anti-inflammatory, analgesic, antibacterial, inhibit microorganism, antiviral and regulation of plant growth.
In order to realize combination of multiform active ingredients, we designed and have synthesized a series of novel thiadiazine, thiosemicarbazide and 1,3,4-thiadiazole derivatives which containing benzimidazole compounds in order to enhance their biological activities. It extended the research field of such compounds and provided abundant leading compounds for later selecting work of effective drugs.
This thesis consists of two major parts:
The first part is about literature review. The progress in application and synthesis of benzoimidazole, thiadiazine, thiosemicarbazide, thiadiazole derivatives and the principle of microwave irradiation and it’s application in organic reactions were systematic exposition.
The second part is about experimental content. Major work as follows:
1. A series of novel 1,2,4-triazolo[3,4-b]- 1',3',4'-thiadiazine derivatives were synthesized by the reaction of 3-(2-substituted benzoimidazole-1-methylene)-4-amino-5-mercapto-1,2, 4-triazole withα-bromoacetophenones under microwave irradiation and heating. Comparison of the conventional refluxing method and microwave irradiation accelerate means, discussed for the results;
2. A series of novel 1-(2-trifluoromethylbenzimidazol-1-acetyl)-4-aroylthiosemicarbazide were synthesized by the reaction of 1-(2-trifluoromethylbenzimidazole-1-yl)acetyl hydrazine with aroylisothiocyanate under microwave irradiation and heating.The preliminary biological activity of the target compounds have been tested;
3. 1-(2-trifluoromethylbenzimidazol-1-acetyl)-4-aroylthiosemicarbazide were synthesized under microwave irradiation. Then compounds were cyclized in acetic acid to afford a series of novel 2-aroylamino-5-(2-trifluoromethylbenzimidazol-1-ylmethyl)-1,3,4-thiadi- azole in excellent yields under microwave irradiation. Comparison of the conventional refluxing method and microwave irradiation accelerate means, discussed for the results.
The innovations of the paper are based on the follow:
1. 3-(2-methyl benzoimidazole-1-methylene)-6-aryl-7H-1',2',4'-triazolo[3,4-b]-1",3",4"- thiadiazine and 3-(2-trifluoromethyl benzoimidazole-1-methylene)-6-aryl-7H-1',2',4' -triazolo[3,4-b]-1",3",4"-thiadiazine were synthesized unreported in the literatures under microwave irradiation. The conditions of microwave irradiation were discussed;
2. A series of novel 1-(2-trifluoromethylbenzimidazol-1-acetyl)-4-aroylthio-semicarbazide were synthesized under microwave irradiation. The preliminary biological activity of the target compounds have been tested, the result show that compound 2a have some anti-HIV-1 reverse transcriptase activity;
3. Ten 2-aroylamino-5-(2-trifluoromethyl-benzimidazol-1-ylmethyl)-1,3,4-thiadiazole were synthesized under microwave irradiation, ten precursor compounds were synthesized under microwave irradiation too. After two steps of the microwave irradiation, high purity products were obtained.
引文
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