氟碳烷基取代噁二唑、三唑的合成及在准外消旋合成中的应用
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摘要
近年来,含氟有机化合物得到广泛的应用,这主要是因为氟原子或含氟链段导致化合物物理、化学和生物学性质产生很大的变化。而1,3,4-噁二唑-2-硫酮具有广谱的生物活性如抗HIV病毒,抗细菌及防止低血糖昏迷等;另一类杂环1,2,4-三唑-5-硫酮也具有抗血压,植物生长调节活性以及舒张血管活性等。关于它们唑环NH上的氢原子的反应已有较多的研究,比较典型的就是Mannich反应,但是对于该氢原子被多氟烷基取代的化合物,却未有文献报道。本文的第二章先用芳香羧酸与氨基酸形成酰胺,然后进行关环得到相应的1,3,4-噁二唑-2-硫酮(2-5)及1,2,4-三唑-5-硫酮(2-8),再利用N-烷基化反应引入多氟烷基,结合唑类杂环化合物良好的生物活性,为筛选出具有活性的多氟唑类化合物做准备,通过改变不同的取代基合成了24个新的目标化合物2-6a ~ 2-6l和2-9a ~ 2-9l。对于化合物2-5a在多氟烷基化反应时,唑环NH和CONH上的氢原子与KOH反应可能分别形成反应中间体2-5a-I、2-5a-II,用Materials Studio 3.0中的Dmol3计算模块理论计算表明了唑环上的NH较之CONH中的NH更易进行烷基化反应,部分化合物的生物活性测试正在进行之中。
光学活性化合物广泛地分布在有机,医药和天然产物中,现在合成旋光对映体有两种方法:外消旋合成随后手性拆分与不对称合成。而本文的第三章介绍第三种方法:准外消旋合成。外消旋合成可同步合成一对对映异构体混合物,但是对它们的分离相当困难。不对称合成用光学纯化合物为原料,但产物的光学纯度小于要求的纯度,产物仍需作进一步的光学拆分。然而,对于两个对映异构体都有应用价值的情况下,例如,要分别研究新手性化合物R-型与S-型的生物特性,必须分别进行两个系列的不对称合成来获得R-型与S-型手性化合物。准外消旋合成如同不对称合成一样,准外消旋合成法以光学纯原料直接合成手性化合物,但是其反应过程又类似外消旋合成,可以同步合成一对纯的对映异构体,特别适合于由氟碳基战略来合成,分离和鉴定一对新的对映异构体。
论文的第三章由对碘苯甲酸作为起始原料,经过酯化,酰肼化,关环,再进行N-多氟烷基化反应,制得两个N-多氟烷基-4-苯基-3-对碘苯基-1,2,4-三唑-5-硫酮,多氟标记分别为C6F13和C8F17;将D、L-构型的丙氨酸酯化,并与对碘苯甲酰氯反应得到酰胺,再运用苯环上的碘原子与三甲基硅烷基乙炔进行第一次Sonogashira偶联得到化合物3-9,然后脱去三甲基硅烷基再释放出炔基,得到两个对乙炔基苯甲酰胺基丙氨酸甲酯。将L-对乙炔基苯甲酰胺基丙氨酸甲酯再与多氟标记是C6F13的N-多氟烷基1,2,4-三唑-5-硫酮进行又一次的Sonogashira偶联,D-构型的则与多氟标记是C8F17的进行偶联,分别得到各自的偶联产物,再把两者等量的均匀混合,得到准外消旋体。将准外消旋体酰肼化,再进行关环,得到2-甲基-4-(4-N-多氟烷基-4-苯基-1,2,4-三唑-5-硫酮苯基)乙炔基苯甲酰胺基1,3,4-噁二唑-2-硫酮;随后再进行准外消旋拆分,得到两个对映异构体。
论文的第四章侧重于席夫碱的合成,也是前面两章研究工作的继续。在杂环化合物合成研究中,使具有不同生物活性的官能团在同一分子中聚集,实现活性叠加,有望开发新的具有高效、广谱活性的新杂环化合物。有鉴于此,我们先将一些含不同取代基的芳香醛引入1,2,4-三唑,合成了一系列1,2,4-三唑-5-硫酮类席夫碱,利用N-烷基化反应在1,2,4-三唑上引入多氟烷基和溴代四乙酰基葡萄糖,根据活性叠加原理,预测得到一系列具有更广谱生物活性的新目标化合物。
糖基化修饰可以显著降低某些天然药物的毒性并改善其吸收,因而目前合成糖基化合物来修饰天然药物已成为药物化学发展的一个重要领域。类维生素A在脊椎动物的生长、发育、以及繁殖等过程中发挥十分重要的作用。但类维生素A在高剂量使用时毒性太强。为提高其药物活性,寻找有更好治疗效果类维A酸衍生物,本文第五章合成两类异维A酸糖衍生物:一类是异维A酸与溴代全乙酰基糖在碱性条件下以4-二甲氨基吡啶做相转移催化剂,直接合成异维A酸糖酯;另外一类是选取香草醛等三个羟基苯甲醛作为双官能团媒介物,将这些分子中的酚羟基与糖基反应,之后再将醛基还原成醇羟基官能团,再与异维A酸相连,合成三个异维A酸糖苷,并将化合物5-2a和5-9a进行脱去乙酰基反应。最后,采用MTT法检测肺癌细胞(A549)对所有化合物耐药性。生物活性测试结果表明,通过双官能团媒介物桥连的异维A酸糖苷较之直接相连的异维A酸糖酯具有更好的活性,而脱乙酰基保护后的含游离羟基的异维A酸糖酯(5-3)或糖苷(5-11)同未脱保护的糖酯(5-2a)或糖苷(5-9a)相比,抗肿瘤活性又进一步增强。
Recently, fluorinated functional compounds have been gained to chemist’s attentions since it was found that the introduction of fluorine atoms or fluorous alkyl into organic molecules could lead to significant changes in biological activities. It has been reported that 1,3,4-oxadiazole and 1,2,4-triazole derivatives having substituted aryl group, such as the 5-substituted phenyl group or a 3,5-disubstituted aryl group, exhibit bactericidal, antiinflammatory, tuberculostatic, anticonvulsion, and fungicidal activities. There a few papers reported the reactivity of the hydrogen of NH group in heterocycle, for example, Mannich base reaction. However, the same hydrogen substituted by perfluoroalkyl is not reported in the literature. Compound 3 was synthesized by reaction of acid chloride with amino acid ester in the presence of Et3N and DMF. After several steps synthesizing, the 1,3,4-oxadiazole-2-thiones(2-5) and 1,2,4-triazole-5-thiones(2-8) were obtained. Combining the oxadiazole and triazole with good activities, two series of N-2-perfluoroalkylethyl-substituted 1,3,4-oxadiazole-2-thiones(2-6a ~ 2-6l) and 1,2,4-triazole-5-thiones(2-9a ~ 2-9l) were synthesized in the second chapter this paper and their structures were confirmed by 1H-NMR, 19F-NMR, IR, mass spectra and elemental analysis. The experimental results and the calculation showed that the hydrogen of NH group in heterocycle was more active than the hydrogen on CONH to finish alkyl-substitution reaction on nitrogen through the computing module Dmol3 of Materials Studio 3.0. Some compounds biological activities are testing.
Chiral compounds abound in organic, medicinal, and natural products chemistry. Today, there are two ways to make enantiopure (or enantioenriched) organic molecules: racemic synthesis followed by resolution, or asymmetric synthesis. The third chapter in this paper introduces herein a third method, quasiracemic synthesis.
Classical racemic synthesis makes both enantiomers of a target compound in a single synthesis, but separation (resolution) and identification of the final enantiomers pose large hurdles. Asymmetric synthesis employs enantiopure compounds, but two separate syntheses are needed if both enantiomers are desired. quasiracemic synthesis unites some of the key advantages of racemic and asymmetric synthesis. However, given two enantiomers with high application, especially, the R- and S- configuration products must studied their biological, chemical properties respectively. Therefore, two series assymetrically synthesis are carried out in order to obtain R- and S- configuration products. It is obviously that the method for original research is a very complicated and difficult when only relying on asymmetric synthesis. Like asymmetric synthesis, quasiracemic synthesis starts and finishes with enantiopure compounds, but like racemic synthesis it provides both enantiomers in a single synthesis.“Quasienantiomers”are used in place of enantiomers, and the separation and identification of the final quasienantiomers is ensured by a tagging strategy.
The third chapter in the present paper using 4-iodine benzoic acid as starting material, two N-perfluoroalkyl-4-phenyl-3-(4-iodinephenyl)-1,2,4-triazole-5-thione are synthesized, the fluorous tagging is C6F13 and C8F17, respectively. The amide are obtained reacts D, L-configuration of the alanine ester with 4-iodinebenzoyl chloride. Two 4-acetylene alaninemethylesters are synthesized after deprotection compounds 3-9 which using the iodine atom on the benzene ring coupled with trimethyl silicon alkyl acetylene. Again Sonogashira coupling are happened between L-configuration 4-acetylene benzamidoalanine methylesters with N-perfluoroalkyl 1,2,4-triazole- 5-thione which the fluorous tagging is C6F13. In similarly, the D-configuration is coupled with triazole which the fluorous tagging is C8F17. Both two products are equal to mix and gain Quasienantiomers. After hydrazide and cyclization, the 2-methly-4-(4-N-perfluoroalkyl-4-phenyl-1,2,4-triazole-5-thione-phenyl)acetylenebenzamido-1,3,4-oxadiazoline-thione are synthesized. Lastely, two enantiopure are obtained after demix.
The forth chapter in the present paper focuses on the synthesis of Schiff-base, in other words, the research is the continuation of the second and third research works. The different biological activity functional group to gather in the identical molecule can realize the active superimposition and develop newly highly-efficient heterocyclic compounds with broad-spectrum activity. Accordingly, the 1,2,4-triazole-5-thione Schiff bases are synthesized by some different substituted aromatic aldehydes react with 1,2,4-triazole. Then, the hydrogen of NH group in heterocycle is substituted by perfluoroalkyl and tetraethyl acyl-glucose, respectively. Based on the activity superposition principle, the compounds with more potential biological activities are hoped to obtain.
Sugar modification can decrease the toxicity and increase absorption of some nature drugs. Nowadays, synthesis of sugar compounds to modify nature drugs has become an important field of pharmaceutical chemistry. Retinoids play an essential role in vertebrate growth and development, supporting cell differentiation; embryonic development, vision, the immune response and reproduction. Retinoids has been found to be too toxic at high dosage levels to be of practical value for cancer prevention in higher mammals. In order to enhance pharmacal effects and gain the relative derivatives with better curing effect and selectivity, structures of retinoic acids were modified by inducing glycosyl groups in this paper. Nine glucuronide conjugates of 13-cis-retinoic acid acid were synthesized in two ways and not reported in literatures until now. A new retinoylation method using of DCC as reagent under catalysis DMAP was developed after evaluated various reaction conditions. The O-glycosylation method was investigated using of DMAP as phase-transfer catalyst. Furthermore, deacetylation of glycosyl retinoates was studied using catalytic amount of dibutyltin oxide as catalyst in methanol. Finally all compounds were determined in vitro by MTT assay using human cancer lines including A549 cells lines etc. Results showed that glucoside derivatives exhibited interesting cytotoxic activities and were stronger than glycosyl esters. Deactylation of 5-3 and 5-11 also improved their bioactivities than those 5-2a and 5-9a, respectively.
光学活性化合物广泛地分布在有机,医药和天然产物中,现在合成旋光对映体有两种方法:外消旋合成随后手性拆分与不对称合成。而本文的第三章介绍第三种方法:准外消旋合成。外消旋合成可同步合成一对对映异构体混合物,但是对它们的分离相当困难。不对称合成用光学纯化合物为原料,但产物的光学纯度小于要求的纯度,产物仍需作进一步的光学拆分。然而,对于两个对映异构体都有应用价值的情况下,例如,要分别研究新手性化合物R-型与S-型的生物特性,必须分别进行两个系列的不对称合成来获得R-型与S-型手性化合物。准外消旋合成如同不对称合成一样,准外消旋合成法以光学纯原料直接合成手性化合物,但是其反应过程又类似外消旋合成,可以同步合成一对纯的对映异构体,特别适合于由氟碳基战略来合成,分离和鉴定一对新的对映异构体。
论文的第三章由对碘苯甲酸作为起始原料,经过酯化,酰肼化,关环,再进行N-多氟烷基化反应,制得两个N-多氟烷基-4-苯基-3-对碘苯基-1,2,4-三唑-5-硫酮,多氟标记分别为C6F13和C8F17;将D、L-构型的丙氨酸酯化,并与对碘苯甲酰氯反应得到酰胺,再运用苯环上的碘原子与三甲基硅烷基乙炔进行第一次Sonogashira偶联得到化合物3-9,然后脱去三甲基硅烷基再释放出炔基,得到两个对乙炔基苯甲酰胺基丙氨酸甲酯。将L-对乙炔基苯甲酰胺基丙氨酸甲酯再与多氟标记是C6F13的N-多氟烷基1,2,4-三唑-5-硫酮进行又一次的Sonogashira偶联,D-构型的则与多氟标记是C8F17的进行偶联,分别得到各自的偶联产物,再把两者等量的均匀混合,得到准外消旋体。将准外消旋体酰肼化,再进行关环,得到2-甲基-4-(4-N-多氟烷基-4-苯基-1,2,4-三唑-5-硫酮苯基)乙炔基苯甲酰胺基1,3,4-噁二唑-2-硫酮;随后再进行准外消旋拆分,得到两个对映异构体。
论文的第四章侧重于席夫碱的合成,也是前面两章研究工作的继续。在杂环化合物合成研究中,使具有不同生物活性的官能团在同一分子中聚集,实现活性叠加,有望开发新的具有高效、广谱活性的新杂环化合物。有鉴于此,我们先将一些含不同取代基的芳香醛引入1,2,4-三唑,合成了一系列1,2,4-三唑-5-硫酮类席夫碱,利用N-烷基化反应在1,2,4-三唑上引入多氟烷基和溴代四乙酰基葡萄糖,根据活性叠加原理,预测得到一系列具有更广谱生物活性的新目标化合物。
糖基化修饰可以显著降低某些天然药物的毒性并改善其吸收,因而目前合成糖基化合物来修饰天然药物已成为药物化学发展的一个重要领域。类维生素A在脊椎动物的生长、发育、以及繁殖等过程中发挥十分重要的作用。但类维生素A在高剂量使用时毒性太强。为提高其药物活性,寻找有更好治疗效果类维A酸衍生物,本文第五章合成两类异维A酸糖衍生物:一类是异维A酸与溴代全乙酰基糖在碱性条件下以4-二甲氨基吡啶做相转移催化剂,直接合成异维A酸糖酯;另外一类是选取香草醛等三个羟基苯甲醛作为双官能团媒介物,将这些分子中的酚羟基与糖基反应,之后再将醛基还原成醇羟基官能团,再与异维A酸相连,合成三个异维A酸糖苷,并将化合物5-2a和5-9a进行脱去乙酰基反应。最后,采用MTT法检测肺癌细胞(A549)对所有化合物耐药性。生物活性测试结果表明,通过双官能团媒介物桥连的异维A酸糖苷较之直接相连的异维A酸糖酯具有更好的活性,而脱乙酰基保护后的含游离羟基的异维A酸糖酯(5-3)或糖苷(5-11)同未脱保护的糖酯(5-2a)或糖苷(5-9a)相比,抗肿瘤活性又进一步增强。
Recently, fluorinated functional compounds have been gained to chemist’s attentions since it was found that the introduction of fluorine atoms or fluorous alkyl into organic molecules could lead to significant changes in biological activities. It has been reported that 1,3,4-oxadiazole and 1,2,4-triazole derivatives having substituted aryl group, such as the 5-substituted phenyl group or a 3,5-disubstituted aryl group, exhibit bactericidal, antiinflammatory, tuberculostatic, anticonvulsion, and fungicidal activities. There a few papers reported the reactivity of the hydrogen of NH group in heterocycle, for example, Mannich base reaction. However, the same hydrogen substituted by perfluoroalkyl is not reported in the literature. Compound 3 was synthesized by reaction of acid chloride with amino acid ester in the presence of Et3N and DMF. After several steps synthesizing, the 1,3,4-oxadiazole-2-thiones(2-5) and 1,2,4-triazole-5-thiones(2-8) were obtained. Combining the oxadiazole and triazole with good activities, two series of N-2-perfluoroalkylethyl-substituted 1,3,4-oxadiazole-2-thiones(2-6a ~ 2-6l) and 1,2,4-triazole-5-thiones(2-9a ~ 2-9l) were synthesized in the second chapter this paper and their structures were confirmed by 1H-NMR, 19F-NMR, IR, mass spectra and elemental analysis. The experimental results and the calculation showed that the hydrogen of NH group in heterocycle was more active than the hydrogen on CONH to finish alkyl-substitution reaction on nitrogen through the computing module Dmol3 of Materials Studio 3.0. Some compounds biological activities are testing.
Chiral compounds abound in organic, medicinal, and natural products chemistry. Today, there are two ways to make enantiopure (or enantioenriched) organic molecules: racemic synthesis followed by resolution, or asymmetric synthesis. The third chapter in this paper introduces herein a third method, quasiracemic synthesis.
Classical racemic synthesis makes both enantiomers of a target compound in a single synthesis, but separation (resolution) and identification of the final enantiomers pose large hurdles. Asymmetric synthesis employs enantiopure compounds, but two separate syntheses are needed if both enantiomers are desired. quasiracemic synthesis unites some of the key advantages of racemic and asymmetric synthesis. However, given two enantiomers with high application, especially, the R- and S- configuration products must studied their biological, chemical properties respectively. Therefore, two series assymetrically synthesis are carried out in order to obtain R- and S- configuration products. It is obviously that the method for original research is a very complicated and difficult when only relying on asymmetric synthesis. Like asymmetric synthesis, quasiracemic synthesis starts and finishes with enantiopure compounds, but like racemic synthesis it provides both enantiomers in a single synthesis.“Quasienantiomers”are used in place of enantiomers, and the separation and identification of the final quasienantiomers is ensured by a tagging strategy.
The third chapter in the present paper using 4-iodine benzoic acid as starting material, two N-perfluoroalkyl-4-phenyl-3-(4-iodinephenyl)-1,2,4-triazole-5-thione are synthesized, the fluorous tagging is C6F13 and C8F17, respectively. The amide are obtained reacts D, L-configuration of the alanine ester with 4-iodinebenzoyl chloride. Two 4-acetylene alaninemethylesters are synthesized after deprotection compounds 3-9 which using the iodine atom on the benzene ring coupled with trimethyl silicon alkyl acetylene. Again Sonogashira coupling are happened between L-configuration 4-acetylene benzamidoalanine methylesters with N-perfluoroalkyl 1,2,4-triazole- 5-thione which the fluorous tagging is C6F13. In similarly, the D-configuration is coupled with triazole which the fluorous tagging is C8F17. Both two products are equal to mix and gain Quasienantiomers. After hydrazide and cyclization, the 2-methly-4-(4-N-perfluoroalkyl-4-phenyl-1,2,4-triazole-5-thione-phenyl)acetylenebenzamido-1,3,4-oxadiazoline-thione are synthesized. Lastely, two enantiopure are obtained after demix.
The forth chapter in the present paper focuses on the synthesis of Schiff-base, in other words, the research is the continuation of the second and third research works. The different biological activity functional group to gather in the identical molecule can realize the active superimposition and develop newly highly-efficient heterocyclic compounds with broad-spectrum activity. Accordingly, the 1,2,4-triazole-5-thione Schiff bases are synthesized by some different substituted aromatic aldehydes react with 1,2,4-triazole. Then, the hydrogen of NH group in heterocycle is substituted by perfluoroalkyl and tetraethyl acyl-glucose, respectively. Based on the activity superposition principle, the compounds with more potential biological activities are hoped to obtain.
Sugar modification can decrease the toxicity and increase absorption of some nature drugs. Nowadays, synthesis of sugar compounds to modify nature drugs has become an important field of pharmaceutical chemistry. Retinoids play an essential role in vertebrate growth and development, supporting cell differentiation; embryonic development, vision, the immune response and reproduction. Retinoids has been found to be too toxic at high dosage levels to be of practical value for cancer prevention in higher mammals. In order to enhance pharmacal effects and gain the relative derivatives with better curing effect and selectivity, structures of retinoic acids were modified by inducing glycosyl groups in this paper. Nine glucuronide conjugates of 13-cis-retinoic acid acid were synthesized in two ways and not reported in literatures until now. A new retinoylation method using of DCC as reagent under catalysis DMAP was developed after evaluated various reaction conditions. The O-glycosylation method was investigated using of DMAP as phase-transfer catalyst. Furthermore, deacetylation of glycosyl retinoates was studied using catalytic amount of dibutyltin oxide as catalyst in methanol. Finally all compounds were determined in vitro by MTT assay using human cancer lines including A549 cells lines etc. Results showed that glucoside derivatives exhibited interesting cytotoxic activities and were stronger than glycosyl esters. Deactylation of 5-3 and 5-11 also improved their bioactivities than those 5-2a and 5-9a, respectively.
引文
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