苯并咪唑與香豆素共軛連結化合物之合成與其構型之探討

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姓名

陳彥儒(Yen-Ju Chen) 查詢紙本館藏

畢業系所

化學學系

論文名稱

苯并咪唑與香豆素共軛連結化合物之合成與其構型之探討
(Conjugation of Benzimidazoles with Coumarins: Their Synthesis and Conformation)

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摘要(中)

我們成功的合成出13個直接將benzimidazole與coumarin連結在一起的化合物，且這些化合物皆可由簡單的化學合成方法獲得。藉由核磁共振圖譜、紅外線光譜以及分子模擬的探討，我們發現benzimidazole上NH的氫原子與coumarin上羰基C=O的氧原子之間，其構型在最穩定能量態下沒有觀察到分子內氫鍵的形成，且可觀察到benzimidazole及coumarin此兩平面分子會藉由單鍵的旋轉以63.967°–85.705°的角度扭轉成非共平面結構。此結果在未來討論結構與抑制C型肝炎的活性關係時，可讓我們忽略氫鍵的影響，並有利於讓我們了解所合成出的化合物對於抑制C型肝炎病毒的作用機制。

摘要(英)

We successfully obtained thirteen hinged benzimidazole–coumarin hybrids; these compounds were obtained by simple chemical synthesis. By studies of the spectra of nuclear magnetic resonance and infrared spectroscopy as well as the outcomes of molecular modeling, we conclude that the conformation with the thermodynamically most stable form did not contain intramolecular hydrogen bondings between the NH proton in benzimidazole and the carbonyl group in coumarin. The angle between benzimidazole and coumarin planes were 63.967°–85.705°. In the future, we will discuss the structure–activity relationship of anti-HCV, the results shall help us to understand the mechanism that the compounds for the inhibition of hepatitis C virus.

關鍵字(中)

★ 構型
★ C型肝炎

關鍵字(英)

★ Coumarin
★ benzimidazole

論文目次

中文摘要 .................................................i
英文摘要 ................................................ii
謝誌 ...................................................iii
目錄 ....................................................iv
圖目錄 ..................................................vi
表目錄 .................................................vii
一、緒論 ................................................1
二、結果 ................................................5
2-1　合成具有不同官能基之3-ethoxycarbonylcoumarins (3a– 3h) .................................................5
2-2　合成一系列hinged Benzimidazole–Coumarin化合物 (5a– 5n) .................................................6
2-3　鑑定hinged Benzimidazole–Coumarin化合物 (5a–5n) ...9
三、討論 ...............................................11
3-1　利用NMR研究產物5a–5n之構型 ........................11
3-2　利用FT-IR研究產物5a–5n之構型 ......................13
3-3　利用分子模擬預測產物5a–5n之構型 ...................19
四、結論 ...............................................24
五、實驗部分 .........................................25
6-Fluoro-3-[2'-(5',6'-dimethyl)benzimidazolyl]coumarin (5a) ....................................................27
6-Chloror-3-[2'-(5',6'-dimethyl)benzimidazolyl]coumarin (5b) ....................................................27
3-[2'-(5',6'-Dimethyl)benzimidazolyl]-6-methylcoumarin (5c) ....................................................28
6-Methoxy-3-[2'-(5',6'-dimethyl)benzimidazolyl]coumarin (5d) ....................................................28
6-Hydroxy-3-[2'-(5',6'-dimethyl)benzimidazolyl]coumarin (5e) ....................................................29
7-Diethylamino-3-[2'-(5',6'-dimethyl)benzimidazolyl]coumarin (5g) ...........................................30
3-[2'-(5'-Bromo)benzimidazolyl]coumarin (5h) ....................................................30
3-[2'-(5'-Chloro)benzimidazolyl]coumarin (5i) ....................................................31
3-[2'-(5',6'-Dichloro)benzimidazolyl]coumarin (5j) ....................................................31
3-[2'-(5'-Chloro)benzimidazolyl]-6-fluorocoumarin (5k) ....................................................32
6-Chloror-3-[2'-(5'-chloro)benzimidazolyl]coumarin (5l) ....................................................32
3-[2'-(5'-Chloro)benzimidazolyl]-6-methylcoumarin (5m) ....................................................33
3-[2'-(5'-Chloro)benzimidazolyl]-6-methoxycoumarin (5n) ....................................................33
六、參考文獻 .........................................35
七、光譜 ...............................................40

參考文獻

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指導教授

胡紀如(Jih Ru Hwu)

審核日期

2010-7-16

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