具有潜在生物活性新型骨架分子的合成方法学研究及其应用
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摘要
本论文主要围绕具有潜在抗肿瘤活性的羟肟酸类组蛋白去乙酰化酶抑制剂的设计与合成来展开,包括：Beckmann重排反应及其应用的方法学研究,基于茚酮骨架的羟肟酸类衍生物的设计与合成以及苯并噻唑衍生物的合成方法学研究三个方面的研究内容。
一、在Beckmann重排反应的方法学研究方面：
我们发展了三个有效催化Beckmann重排的反应体系,包括：10mol%BF3·Et2O、2 mol% TsCl/2 mol% ZnCl2、5 mol% NBS/5 mol% PPh3。以上三个催化体系均可以高效催化酮肟的Beckmann重排反应。
同时,我们对有机小分子催化Beckmann重排的反应机理进行了深入细致的研究。研究发现Yamamoto等人提出的新型催化机理与我们的实验结果存在矛盾。为此,我们认为有机小分子催化Beckmann重排反应依然遵循经典的酸催化重排机理,而有机小分子则是通过与酮肟反应,现场释放等当量的酸而发挥催化作用。因此,有机小分子只是作为反应的引发剂而非真正的催化剂。我们进一步研究发现酸催化剂的酸性强弱对Beckmann重排有显著的影响,酸性越强,重排反应越易于发生。
另外,我们发展了磺酰氯参与的基于酮肟Beckmann重排的“一锅法”制备N-酰亚胺苯并三氮唑类化合物的高效合成方法。该合成方法具有反应条件温和,操作简便,原料廉价易得,反应收率高,底物适用范围较广等特点。
二、在基于茚酮骨架的羟肟酸类化合物的设计与合成方面：
我们以6-溴-1-茚酮为原料,经6-7步反应,分别以18%,9%和9%的总收率合成得到羟肟酸类目标化合物Rac-Ⅰ-60a, Rac-Ⅰ-60b和Rac-Ⅰ-60c。以6-溴-1-茚酮为原料,应用aldol缩合反应在茚酮2位衍生化,经NaBH4还原后,以Heck反应构建肉桂基并发生双键异构化,合成得到茚酮衍生物Ⅲ-34a等重要中间体,并分别以0.6%,0.4%和1.0%的总收率,经9-10步反应,合成得到了一系列基于茚酮骨架目标化合物Ⅲ-40 a,Ⅲ-40b和Ⅲ-40c。
目前,该两类化合物的药理学活性测试正在进行之中。
三、在苯并噻唑衍生物的合成方法学研究方面：
我们发现用mCPBA来氧化2-(N-乙基-2-苯并噻唑)-乙酸甲酯所得产物的结构与文献报道结果不一致。在此基础上,我们发展了温和、高效、可控的选择性氧化方法。通过选用mCPBA和DDQ两种不同的氧化剂,我们实现了同一底物的选择性氧化生成结构完全不同的两类化合物。最后,我们以2-氨基-6-硝基苯并噻唑为起始原料,经4步反应,以6.5%的总收率合成得到关键中间体2-(N-甲基-6-胺基-2-苯并噻唑)-乙酸乙酯,为后续合成目标化合物奠定基础。
This dissertation mainly focused on the design and synthesis of potential anti-tumor active small-molecule hydroxamic acid histone deacetylase inhibitors (HDACi). The primary coverage includes three aspects of studies:Beckmann rearrangement and its application; Design and synthesis of indanone-based hydroxamic acid derivatives; Synthetic methodologies for benzothiazole derivatives.
1. Beckmann rearrangement and its application:
Three highly efficient catalytic systems for Beckmann rearrangement of ketoximes were developed, which includes 10 mol%BF3·Et2O,2 mol%TsCl/2 mol%ZnCl2 and 5 mol% NBS/5 mol%PPh3.
Meanwhile, we examined the mechanism of Beckmann rearrangement catalyzed by small organic molecule intensively, and found that newly proposed mechanism by Yamamoto is contradictive to our experiments. As a consequent, we proposed that the Beckmann rearrangement catalyzed by small organic molecules still obeyed the classical well-recognized acid-catalyzed mechanism. Notably, small organic molecule was proposed to react with ketoxime and followed by releasing in-situ equal equivalent of acid, which acts the real catalyst to play the catalytic role. Therefore, small organic molecule actually is the initiator instead of the catalyst. Further study indicated that the degree of acidity of acid-catalysts affected the Beckmann rearrangement significantly. The more acidic, the easier the rearrangement proceeds.
In addition, we have developed a facile one-pot strategy for synthesis of N-imidoylbenzotriazoles via sulfonyl chloride mediated Beckmann rearrangement of ketoximes. There are some merits of this newly developed synthetic method, such as easy manipulation, easily available starting materials, high yield and generality of the substrate and so on.
2. Design and synthesis of indanone-based hydroxamic acid derivatives:
Three hydroxamic acid target compounds Rac-Ⅰ-60a, Rac-Ⅰ-60b and Rac-Ⅰ-60c were prepared via 6 or 7 steps with 6-bromo-l-indanone as starting material with overall yield 18%, 9%and 9%, respectively. In addition, Aldol condensation at position 2 of 6-bromo-l-indanone, then reduction with NaBH4, followed by constructing cinnamyl moiety via Heck reaction and subsequent Pd-mediated isomerization of double bond, afforded the key indanone-based intermediatesⅢ-34a. Finally, another series of target compoundsⅢ-40a,Ⅲ-40b andⅢ-40c were accomplished via 9-10 steps with the overall yield 0.6%,0.4%and 1.0%, respectively.
The bioassays of biological activities of these two types of target compounds are ongoing.
3. Synthetic methodologies for benzothiazole derivatives:
We found that the mCPBA oxidation of methyl 2-(N-ethyl-2,3-dihydrobenzothiazol-2-yl) acetate gave corresponding product with different structure when compared to that of reported one. On this basis, a facile, mild and highly controllable oxidation method was developed. Two different compounds were obtained when the same substrate were oxidized with different reagents, mCPBA or DDQ. Lastly, the key intermediate ethyl 2-(6-amino-N-methyl-2, 3-dihydrobenzo-thiazol-2-yl)-acetate was synthesized via 4 steps with the overall yield 6.5% using 2-amine-6-nitrobenzothiazole as a starting material.
一、在Beckmann重排反应的方法学研究方面：
我们发展了三个有效催化Beckmann重排的反应体系,包括：10mol%BF3·Et2O、2 mol% TsCl/2 mol% ZnCl2、5 mol% NBS/5 mol% PPh3。以上三个催化体系均可以高效催化酮肟的Beckmann重排反应。
同时,我们对有机小分子催化Beckmann重排的反应机理进行了深入细致的研究。研究发现Yamamoto等人提出的新型催化机理与我们的实验结果存在矛盾。为此,我们认为有机小分子催化Beckmann重排反应依然遵循经典的酸催化重排机理,而有机小分子则是通过与酮肟反应,现场释放等当量的酸而发挥催化作用。因此,有机小分子只是作为反应的引发剂而非真正的催化剂。我们进一步研究发现酸催化剂的酸性强弱对Beckmann重排有显著的影响,酸性越强,重排反应越易于发生。
另外,我们发展了磺酰氯参与的基于酮肟Beckmann重排的“一锅法”制备N-酰亚胺苯并三氮唑类化合物的高效合成方法。该合成方法具有反应条件温和,操作简便,原料廉价易得,反应收率高,底物适用范围较广等特点。
二、在基于茚酮骨架的羟肟酸类化合物的设计与合成方面：
我们以6-溴-1-茚酮为原料,经6-7步反应,分别以18%,9%和9%的总收率合成得到羟肟酸类目标化合物Rac-Ⅰ-60a, Rac-Ⅰ-60b和Rac-Ⅰ-60c。以6-溴-1-茚酮为原料,应用aldol缩合反应在茚酮2位衍生化,经NaBH4还原后,以Heck反应构建肉桂基并发生双键异构化,合成得到茚酮衍生物Ⅲ-34a等重要中间体,并分别以0.6%,0.4%和1.0%的总收率,经9-10步反应,合成得到了一系列基于茚酮骨架目标化合物Ⅲ-40 a,Ⅲ-40b和Ⅲ-40c。
目前,该两类化合物的药理学活性测试正在进行之中。
三、在苯并噻唑衍生物的合成方法学研究方面：
我们发现用mCPBA来氧化2-(N-乙基-2-苯并噻唑)-乙酸甲酯所得产物的结构与文献报道结果不一致。在此基础上,我们发展了温和、高效、可控的选择性氧化方法。通过选用mCPBA和DDQ两种不同的氧化剂,我们实现了同一底物的选择性氧化生成结构完全不同的两类化合物。最后,我们以2-氨基-6-硝基苯并噻唑为起始原料,经4步反应,以6.5%的总收率合成得到关键中间体2-(N-甲基-6-胺基-2-苯并噻唑)-乙酸乙酯,为后续合成目标化合物奠定基础。
This dissertation mainly focused on the design and synthesis of potential anti-tumor active small-molecule hydroxamic acid histone deacetylase inhibitors (HDACi). The primary coverage includes three aspects of studies:Beckmann rearrangement and its application; Design and synthesis of indanone-based hydroxamic acid derivatives; Synthetic methodologies for benzothiazole derivatives.
1. Beckmann rearrangement and its application:
Three highly efficient catalytic systems for Beckmann rearrangement of ketoximes were developed, which includes 10 mol%BF3·Et2O,2 mol%TsCl/2 mol%ZnCl2 and 5 mol% NBS/5 mol%PPh3.
Meanwhile, we examined the mechanism of Beckmann rearrangement catalyzed by small organic molecule intensively, and found that newly proposed mechanism by Yamamoto is contradictive to our experiments. As a consequent, we proposed that the Beckmann rearrangement catalyzed by small organic molecules still obeyed the classical well-recognized acid-catalyzed mechanism. Notably, small organic molecule was proposed to react with ketoxime and followed by releasing in-situ equal equivalent of acid, which acts the real catalyst to play the catalytic role. Therefore, small organic molecule actually is the initiator instead of the catalyst. Further study indicated that the degree of acidity of acid-catalysts affected the Beckmann rearrangement significantly. The more acidic, the easier the rearrangement proceeds.
In addition, we have developed a facile one-pot strategy for synthesis of N-imidoylbenzotriazoles via sulfonyl chloride mediated Beckmann rearrangement of ketoximes. There are some merits of this newly developed synthetic method, such as easy manipulation, easily available starting materials, high yield and generality of the substrate and so on.
2. Design and synthesis of indanone-based hydroxamic acid derivatives:
Three hydroxamic acid target compounds Rac-Ⅰ-60a, Rac-Ⅰ-60b and Rac-Ⅰ-60c were prepared via 6 or 7 steps with 6-bromo-l-indanone as starting material with overall yield 18%, 9%and 9%, respectively. In addition, Aldol condensation at position 2 of 6-bromo-l-indanone, then reduction with NaBH4, followed by constructing cinnamyl moiety via Heck reaction and subsequent Pd-mediated isomerization of double bond, afforded the key indanone-based intermediatesⅢ-34a. Finally, another series of target compoundsⅢ-40a,Ⅲ-40b andⅢ-40c were accomplished via 9-10 steps with the overall yield 0.6%,0.4%and 1.0%, respectively.
The bioassays of biological activities of these two types of target compounds are ongoing.
3. Synthetic methodologies for benzothiazole derivatives:
We found that the mCPBA oxidation of methyl 2-(N-ethyl-2,3-dihydrobenzothiazol-2-yl) acetate gave corresponding product with different structure when compared to that of reported one. On this basis, a facile, mild and highly controllable oxidation method was developed. Two different compounds were obtained when the same substrate were oxidized with different reagents, mCPBA or DDQ. Lastly, the key intermediate ethyl 2-(6-amino-N-methyl-2, 3-dihydrobenzo-thiazol-2-yl)-acetate was synthesized via 4 steps with the overall yield 6.5% using 2-amine-6-nitrobenzothiazole as a starting material.
引文
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