本文選題：吡咯生物堿　切入點：嘧啶酮　出處：《海南大學(xué)》2014年碩士論文　論文類型：學(xué)位論文

【摘要】：含吡咯環(huán)的生物堿廣泛存在于海洋天然產(chǎn)物中,有著廣泛的生物活性。應(yīng)用合成的方法合成含吡咯環(huán)的生物堿,對保護海洋資源和開發(fā)海洋藥物有著重要意義。本文論文采用Biginelli反應(yīng),應(yīng)用固相無溶劑多組分的合成方法,共設(shè)計合成了32個化合物,且都是首次報道的新化合物。使用薄層色譜(TLC)、核磁共振儀(1HMNR)、紅外儀(IR)、質(zhì)譜儀(LC-MS)等分析測試方法,對合成的所有化合物進行了結(jié)構(gòu)驗證和表征。對合成的吡咯二氫嘧啶酮類化合物的生物活性進行初步研究,通過抑菌實驗了解這類化合物的抑菌性質(zhì)。主要內(nèi)容如下： 第一部分：系統(tǒng)的介紹了海洋生物堿,并具體闡述了吡咯和嘧啶兩大類化合物的研究現(xiàn)狀、發(fā)展和活性等情況。同時介紹多組分合成、目標導(dǎo)向合成和綠色合成等合成方法。以此為基礎(chǔ),提出確定本論文課題以及研究的目標。 第二部分：通過對文獻合成條件進行優(yōu)化,應(yīng)用knorr合成法,以THF-HAc-H2O為溶劑,獲得了中間體化合物A1-A5。然后,以硝酸鈰銨為氧化劑對化合物A1-A5進一步氧化,獲得吡咯醛類衍生物B1-B5。最終,對合成的5個吡咯醛類化合物的性質(zhì)和合成條件進行研究討論。 第三部分：以尿素(硫脲)、乙酰乙酸乙酯(乙酰乙酸甲酯、乙酰丙酮或苯甲酰丙酮)、吡咯醛類化合物B1-B5為原料,磷酸為催化劑,通過Biginelli反應(yīng)多組分無溶劑縮合反應(yīng),獲得16個吡咯-氧代二氫嘧啶酮類化合物和16個吡咯-硫代二氫嘧啶酮類化合物,并對其性質(zhì)和合成條件進行研究討論。 第四部分：對所合成的目標產(chǎn)物進行抑菌活性研究,研究菌種選用溶藻弧菌、副溶血性弧菌、枯草芽孢桿菌、糞鏈球菌、綠膿假單胞菌、熒光假單胞菌、尖孢鐮刀菌、白地霉、酵母菌。實驗結(jié)果表明,合成的化合物對選取的細菌和真菌沒有抑制作用。
[Abstract]:Alkaloids containing pyrrole ring are widely present in marine natural products and have a wide range of biological activities. In this paper, 32 compounds were designed and synthesized by Biginelli reaction and solid phase solvent-free multicomponent synthesis. TLC, 1HMNRX, IR, LC-MS, and so on. The structures of all the synthesized compounds were confirmed and characterized. The biological activities of the synthesized pyrrolidine compounds were preliminarily studied, and the bacteriostatic properties of these compounds were studied by bacteriostasis experiments. The main contents were as follows:. Part one: the marine alkaloids are introduced systematically, and the research status, development and activity of pyrrole and pyrimidine are described in detail. On the basis of the synthesis methods such as goal-oriented synthesis and green synthesis, this paper proposes the subject of this paper and the research objectives. The second part: by optimizing the synthesis conditions of literature, using knorr synthesis method, using THF-HAc-H2O as solvent, the intermediate compound A _ 1-A _ 5 was obtained. Then cerium ammonium nitrate was used as oxidant to further oxidize compound A _ 1-A _ 5. Pyrrolidone derivatives B _ 1-B _ 5 were obtained. Finally, the properties and synthesis conditions of five pyrrolides were studied and discussed. The third part: using urea (thiourea), ethyl acetoacetate (methyl acetoacetate, acetylacetone or benzoyl acetone), pyrrolidone compounds B1-B5 as raw material and phosphoric acid as catalyst, multicomponent solvent-free condensation reaction was carried out through Biginelli reaction. Sixteen pyrrole-oxo-dihydropyrimidinone compounds and 16 pyrrole-thio-dihydropyrimidinone compounds were obtained, and their properties and synthesis conditions were discussed. Part 4th: the bacteriostatic activity of the synthesized target product was studied. The strains of Vibrio alginolyticus, Vibrio parahaemolyticus, Bacillus subtilis, Streptococcus faecalis, Pseudomonas aeruginosa, Pseudomonas fluorescein, Fusarium oxysporum were selected. The experimental results showed that the synthesized compounds had no inhibitory effect on selected bacteria and fungi.
【學(xué)位授予單位】：海南大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2014
【分類號】：R914;R96

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本文編號：1579029