2，5-二取代-1，3，4-噻二唑、苯并噁唑啉酮衍生物、螺烯三类化合物的合成、表征及生物活性研究
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摘要
1:采用微波辐射与相转移催化联用技术,以自行合成的芳甲酰肼和对硝基苯甲酰氯为原料,采用一锅法合成出了10个酰氨基硫脲中间体化合物(5a～5j),其中有6个化合物(5d,5f～5j)为新化合物。将所得酰氨基硫脲(5)在无酸催化剂存在下以DMF为溶剂加热回流,脱水关环合成出了9个2,5-二取代-1,3,4-噻二唑类化合物(TM-I-6a～6i),其中有7个(TM-I-6b～6d,TM-I-6f～6i)为新化合物。为合成新目标化合物还合成了31个相关中间体化合物。这种合成1,3,4-噻二唑环的方法目前尚未见文献报道。此合成方法具有操作简单、反应条件温和、后处理简单、经济、环境友好等特点,体现了绿色化学的思想。利用IR、~1H NMR及元素分析确定了中间体及目标产物的结构。首次利用~1H NMR谱和熔点证明了酰氨基硫脲存在着链状和环状两种异构体,首次采用重结晶方法分离得到两种异构体,并得到了它们的IR和~1H NMR谱。对所合成的目标产物2,5-二取代-1,3,4-噻二唑类化合物TM-I-6a～6i进行了大肠杆菌甲硫氨酸肽酶-1(EcMetAP-1)和酵母甲硫氨酸肽酶-1(ScMetAP-1)抑制剂测试实验,实验结果表明:目标产物TM-I-6c,TM-I-6i对EcMetAP-1的抑制率为100%,抑制活性优于阳性对照物L288,TM-I-6g的抑制率为80%,三个样品抑制作用明显,抗菌活性较强。目标化合物TM-I-6c,TM-I-6d,TM-I-6e对ScMetAP-1的抑制作用明显,为100%完全抑制,抗菌活性非常强,抑制活性优于阳性对照物L288。这些研究结果对进一步研究噻二唑化合物的合成、结构解析、生物活性的研究、药物的开发具有十分重要的意义。
2:以邻氨基苯酚和尿素为起始原料经一系列反应合成出了1O个新的具有噻二唑基团的苯并噁唑啉酮衍生物,即2-(芳甲酰氨基)-5-(2-苯并噁唑啉酮-3-甲基)-1,3,4-噻二唑。为合成新化合物还合成了23个相关的中间体化合物。在合成1,3,4-噻二唑环的步骤中采用酸催化脱水关环方法,提高了目标产物的产率。此方法反应时间短,产率高,后处理简单,合环步骤在室温下即可进行。目标化合物及中间体化合物的结构利用IR、~1H NMR、进行了结构表征。对所合成的目标分子,即苯并噁唑啉酮衍生物进行了人源甲硫氨酸肽酶-1(HsMetAP-1)和半胱氨酸天冬氨酸位点特异性蛋白水解酶-1(Caspase-1)抑制实验,结果表明:所合成苯并噁唑啉酮衍生物,对HsMetAP-1和Caspase-1无明显抑制活性。这些研究结果对进一步研究苯并噁唑啉酮衍生物的合成、结构修饰、生物活性的研究、新型非类固醇抗炎药物(NSAIDs)的开发具有十分重要的意义。
3:以5-叔丁基-1,3-二甲苯和液溴为起始原料,经过溴代、氧化、酯化、Ullamnn偶联、环化反应最终合成出了具有光电活性的目标产物TM-Ⅲ-5,即7-叔丁基-13b-氮杂-萘并[3,2,1-de]蒽-5,9-二酮。目标化合物及中间体化合物的结构利用IR、~1H NMR进行了结构表征。在利用Ullamnn反应合成中间体三芳胺二酸时改进了文献的合成方法,采用了CuCl为催化剂、1,10-菲啰啉为配体,使反应时间大大缩短,产物的产率较高,简化了合成与后处理步骤。在合成目标产物7-叔丁基-13b-氮杂-萘并[3,2,1-de]蒽-5,9-二酮时,改进了文献对其的纯化方法,使后处理纯化操作简便,产率较高。此项工作的完成为我们合成出更多新型螺烯化合物、研究其性质提供了有利的实验数据,奠定了实验基础。
1.Ten aroyl thiosemicarbazides(5a～5j) were obtained by the reaction arylbenzoyl hydrazides with 4-nitrobenzoyl chloride under microwave irradiation and phase transfer catalysis(PEG-400).And then,nine 2-aryl-5-(4-nitro benzamido)-1,3, 4-thiadiazoles(6a～6i) were synthesized by the compounds 5 under reflux in DMF.The compounds 5d,5f～5j,6b～6d and 6f～6i are new compounds. Synthesis method of the target compounds is simple,temperate and easily available.Target compounds 6 can be obtained directly without acid catalysis. we also synthesized 31 related intermediate compounds for synthesizing new target compounds.The two isomers of compounds 5 were demonstrated by IR and ~1H NMR.The structures of the target compounds 6 were characterized by IR, ~1H NMR and elemental analysis.The experiments of the biological activity for target molecules(TM-Ⅰ-6a～6i) were accomplished.EcMetAP-1 inhibiting experimental results show that:the arget compound TM-Ⅰ-6c,TM-Ⅰ-6i inhibiting rate is 100%to EcMetAP-1,and TM-Ⅰ-6g inhibiting rate is 80%, three sample inhibitory actions is obvious,and the antibacterial activity is strong. ScMetAP-1 inhibiting experimental results show that:the arget compound TM-Ⅰ-6c,TM-Ⅰ-6d,TM-Ⅰ-6e's inhibiting rate is 100%,the antibacterial activity is very strong.These findings for further research thiadiazole synthesis, biological activity,drug development are very important.
2:2,5-Di-substituted 1,3,4--thiadiazoles containing 2-benzoxazolinones 7a～7j have been obtained by a series of reactions.High yield,short reaction time,mild condition,and easy work-up are advantages of this methodology.The target compounds are all new compounds.Also synthesized 23 related intermediate compounds for synthesizing new target compounds.The structures of the target compounds were characterized by IR,~1H NMR.The experiments of the biological activity for target molecules(TM-Ⅱ-7a～7j) were accomplished. HsMetAP-1 inhibiting experimental results show that:inhibitory activity of the target compounds is not obvious and the antibacterial activity is weak.Caspase-1 inhibiting experimental results show that:the arget compounds have no antibacterial activity.These findings to further study of the synthesis of Benzoxazolinone derivative,the biological activity and the new development of non-steroidal anti-inflnmmatorv drugs(NSAIDs) are very significant.
3:A kind of bridged triarylamines,which is one of the new class heterohelicenes, have been synthesized through oxidation,esterification,Ullmann coupling, cyclization from the starting compounds 5-tert-butyl-1,3-dimethylbenzene and bromine.Finally,we obtained the ultimate objective of synthetic product TM-Ⅲ-5 through a series of improved Synthetic Methods.The structures of the target compound 7-tert-Butyl-13b-aza-naphtho[3,2,1-de]anthracene-5,9-dione was characterized by IR,~1H NMR.The reaction of Ullmann coupling and cyclization was carried out using a improved two-step procedure.Short reaction time and easy work-up are the advantages of this methodology.These findings and datas to further study of the synthesis of heterohelicenes derivative,the optical activity and the new materials development are very significant.
2:以邻氨基苯酚和尿素为起始原料经一系列反应合成出了1O个新的具有噻二唑基团的苯并噁唑啉酮衍生物,即2-(芳甲酰氨基)-5-(2-苯并噁唑啉酮-3-甲基)-1,3,4-噻二唑。为合成新化合物还合成了23个相关的中间体化合物。在合成1,3,4-噻二唑环的步骤中采用酸催化脱水关环方法,提高了目标产物的产率。此方法反应时间短,产率高,后处理简单,合环步骤在室温下即可进行。目标化合物及中间体化合物的结构利用IR、~1H NMR、进行了结构表征。对所合成的目标分子,即苯并噁唑啉酮衍生物进行了人源甲硫氨酸肽酶-1(HsMetAP-1)和半胱氨酸天冬氨酸位点特异性蛋白水解酶-1(Caspase-1)抑制实验,结果表明:所合成苯并噁唑啉酮衍生物,对HsMetAP-1和Caspase-1无明显抑制活性。这些研究结果对进一步研究苯并噁唑啉酮衍生物的合成、结构修饰、生物活性的研究、新型非类固醇抗炎药物(NSAIDs)的开发具有十分重要的意义。
3:以5-叔丁基-1,3-二甲苯和液溴为起始原料,经过溴代、氧化、酯化、Ullamnn偶联、环化反应最终合成出了具有光电活性的目标产物TM-Ⅲ-5,即7-叔丁基-13b-氮杂-萘并[3,2,1-de]蒽-5,9-二酮。目标化合物及中间体化合物的结构利用IR、~1H NMR进行了结构表征。在利用Ullamnn反应合成中间体三芳胺二酸时改进了文献的合成方法,采用了CuCl为催化剂、1,10-菲啰啉为配体,使反应时间大大缩短,产物的产率较高,简化了合成与后处理步骤。在合成目标产物7-叔丁基-13b-氮杂-萘并[3,2,1-de]蒽-5,9-二酮时,改进了文献对其的纯化方法,使后处理纯化操作简便,产率较高。此项工作的完成为我们合成出更多新型螺烯化合物、研究其性质提供了有利的实验数据,奠定了实验基础。
1.Ten aroyl thiosemicarbazides(5a～5j) were obtained by the reaction arylbenzoyl hydrazides with 4-nitrobenzoyl chloride under microwave irradiation and phase transfer catalysis(PEG-400).And then,nine 2-aryl-5-(4-nitro benzamido)-1,3, 4-thiadiazoles(6a～6i) were synthesized by the compounds 5 under reflux in DMF.The compounds 5d,5f～5j,6b～6d and 6f～6i are new compounds. Synthesis method of the target compounds is simple,temperate and easily available.Target compounds 6 can be obtained directly without acid catalysis. we also synthesized 31 related intermediate compounds for synthesizing new target compounds.The two isomers of compounds 5 were demonstrated by IR and ~1H NMR.The structures of the target compounds 6 were characterized by IR, ~1H NMR and elemental analysis.The experiments of the biological activity for target molecules(TM-Ⅰ-6a～6i) were accomplished.EcMetAP-1 inhibiting experimental results show that:the arget compound TM-Ⅰ-6c,TM-Ⅰ-6i inhibiting rate is 100%to EcMetAP-1,and TM-Ⅰ-6g inhibiting rate is 80%, three sample inhibitory actions is obvious,and the antibacterial activity is strong. ScMetAP-1 inhibiting experimental results show that:the arget compound TM-Ⅰ-6c,TM-Ⅰ-6d,TM-Ⅰ-6e's inhibiting rate is 100%,the antibacterial activity is very strong.These findings for further research thiadiazole synthesis, biological activity,drug development are very important.
2:2,5-Di-substituted 1,3,4--thiadiazoles containing 2-benzoxazolinones 7a～7j have been obtained by a series of reactions.High yield,short reaction time,mild condition,and easy work-up are advantages of this methodology.The target compounds are all new compounds.Also synthesized 23 related intermediate compounds for synthesizing new target compounds.The structures of the target compounds were characterized by IR,~1H NMR.The experiments of the biological activity for target molecules(TM-Ⅱ-7a～7j) were accomplished. HsMetAP-1 inhibiting experimental results show that:inhibitory activity of the target compounds is not obvious and the antibacterial activity is weak.Caspase-1 inhibiting experimental results show that:the arget compounds have no antibacterial activity.These findings to further study of the synthesis of Benzoxazolinone derivative,the biological activity and the new development of non-steroidal anti-inflnmmatorv drugs(NSAIDs) are very significant.
3:A kind of bridged triarylamines,which is one of the new class heterohelicenes, have been synthesized through oxidation,esterification,Ullmann coupling, cyclization from the starting compounds 5-tert-butyl-1,3-dimethylbenzene and bromine.Finally,we obtained the ultimate objective of synthetic product TM-Ⅲ-5 through a series of improved Synthetic Methods.The structures of the target compound 7-tert-Butyl-13b-aza-naphtho[3,2,1-de]anthracene-5,9-dione was characterized by IR,~1H NMR.The reaction of Ullmann coupling and cyclization was carried out using a improved two-step procedure.Short reaction time and easy work-up are the advantages of this methodology.These findings and datas to further study of the synthesis of heterohelicenes derivative,the optical activity and the new materials development are very significant.
引文
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