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研究生:施美秀
研究生(外文):Mei-Hsiu Shih
論文名稱:4-雜環取代雪梨酮衍生物的合成與性質研究
論文名稱(外文):Studies on the Syntheses and Properties of 4-Heterocyclic Substituted Sydnone Derivatives
指導教授:葉茂榮葉茂榮引用關係
指導教授(外文):Mou-Yung Yeh
學位類別:博士
校院名稱:國立成功大學
系所名稱:化學系碩博士班
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2002
畢業學年度:90
語文別:中文
論文頁數:146
中文關鍵詞:雪梨酮雜環化合物
外文關鍵詞:heterocyclic compoundssydnones
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許多雪梨酮化合物具有生理活性與藥理作用,雜環化合物如三�t、四�t雜環等衍生物亦具有藥理活性;因而3-芳香基-4-雜環基雪梨酮化合物的合成是相當引人興趣的研究。有關此系列的研究,大多數在雪梨酮的第4位置接上一些官能基,做為雜環基的前導體,再加以環化,即可合成可能具有生理或藥理活性的雪梨酮雜環化合物。本文首先採用3-芳香基雪梨酮-4-甲�T醯氯為起始原料與水合�B進行親核反應後,再與醛類進行環化反應以合成4-三�t雜環基雪梨酮。另外又以疊氮化鈉與3-芳香基雪梨酮-4-甲�T醯氯反應,生成相對應的3-芳香基雪梨酮-4-甲醯疊氮�T,再與醯氯化物作用,則環化生成安定的4-四�t雜環基雪梨酮化合物。由於3-芳香基雪梨酮-4-甲�T醯氯在製備上較為費時、耗力,故本論文力求開拓新的雜環基前導體,基於醛類化合物與活性亞甲基化合物進行 Knoevenagel縮合反應,可獲得含多官能基之衍生物,故本文乃應用此反應於3-芳香基-4-甲醯雪梨酮,並將縮合產物進一步環化以生成4-雜環基雪梨酮。由於雜環取代的查耳酮(chalcones)衍生物具有特殊生理活性,早已被科學家所製備研究,此類α,β-不飽和酮為應用廣泛的合成先導物,可用於合成相對應的�@�t�F、異�Q�t�F等衍生物,而其中1H-�@�t、4,5-二氫-1H-�@�t化合物因具有特殊的抗菌、抗氧化能力,故廣泛地被應用於醫藥及農業,於是許多合成此類雜環化合物的方法因應而生,且為科學家們所熱衷。而雪梨酮衍生物亦具有抗發炎、止痛等生理活性,為了進一步了解兩種雜環的結合效應,故本文著重於雪梨酮環取代的�@�t化合物合成,一方面應用Knoevenagel縮合產物為起始原料,一方面則利用3-芳香基-4-甲醯雪梨酮及4-乙醯-3-芳香基雪梨酮合成其他不同類型的α,β-不飽和酮先導物,再將所合成的各種先導物與水合�B作用,以生成1H-�@�t或1H-�@�t�F衍生物,並探討其反應性。最後篩選部份所合成的3-(3-芳香基雪梨酮-4-基)-5-芳香基-4,5-二氫-1H-�@�t化合物,進行抗細菌、抗真菌探討,並企盼能尋找具有抗生活性的�@�t衍生物。
Many sydnone compounds have been found to have pharmacological and biological activities. On the other hand, various heterocyclic compounds, such as triazoles, tetrazoles etc., are also well known to show special pharmacological activities. Therefore, it should be significant to synthesize 4-heterocyclic sydnones. The most common routes for the synthesis of such compounds are introducing suitable functional groups at the 4-position of sydnones to give the corresponding precursors which then cyclize with other reagents to produce the desired compounds.
In this work, 3-arylsydnone-4-carbohydroximic acid chlorides were used as starting material which reacted with hydrazine hydrate and then cyclized with aldehydes to give 3-aryl-4-triazolyl sydnone derivatives. In addition, 3-arylsydnone -4-carbohydroximic acid chlorides could react with sodium azide to produce the corresponding 3-arylsydnone-4-carbazidoximes. The carbazidoximes then cyclize directly with carboxylic acid chlorides to give tetrazole derivatives.
Because the preparations of 3-arylsydnone-4-carbohydroximic acid chlorides are more time and labor-consuming, it is necessary to develop more convenient precursors for the synthesis of 4-heterocyclic sydnones. Therefore, 3-aryl-4-formyl- sydnones were employed to react with various activated methylene compounds to afford a variety of multifunctional α,β-unsaturated ketones. The reactions of such precursors with different cyclizing reagents were studied and discussed.
Heterocyclic analogues of chalcones have been prepared for biological studies. Theα,β-unsaturated ketones can play as versatile precursors in the syntheses of the corresponding pyrazoline and isoxazoline derivatives. Furthermore, 1H-pyrazoles and 4,5-dihydro-1H-pyrazoles have been found to have diverse applications in medicine and agriculture. In particular, they are known as potent antibiotic and antioxidant agents. Hence, methods capable of generating this type of heterocycles are very attractive. Many sydnone derivatives are also associated with wide variety of physiological activities such as antiinflammatory and analgesic properties. In order to know the combined effect of both pyrazoline and sydnone moieties, this study take up the syntheses of sydnonyl substituted pyrazoles. In order to obtain the desired 3,5-disubstituted-4,5-dihydro-1H-pyrazoles, three type of sydnonyl substituted α,β-unsaturated ketones were synthesized by the following methods: (1) The Claisen-Schmidt condensation of 3-aryl-4-formylsydnones with acetophenone or acetone; (2) The Claisen-Schmidt condensation of 4-acetyl-3-arylsydnones with various aryl aldehydes; (3) The Knoevenagel condensation of 3-aryl-4-formyl- sydnones with various activated methylene compounds. Finally, the 1H-pyrazoline derivatives were synthesized successfully through the reactions of appropriateα,β-unsaturated ketone precursors and hydrazine hydrate. Some selected 1H-pyrazoline products were screened for their antibacterial and antifungal activities.
誌謝
論文摘要
第一章 雪梨酮化合物的簡介…………………………… 1
第二章 三�t及四�t基雪梨酮衍生物的合成
一、前言……………………………………………12
二、結果與討論…………………………………..16
三、實驗部分………………………………………32
四、參考文獻………………………………………52
第三章 3-芳香基-4-甲醯雪梨酮的Knoevenagel
反應及縮合產物之環化
一、前言…………………………………………….56
二、結果與討論…………………………………….57
三、實驗部分……………………………………….72
四、參考文獻……………………………………….98
第四章 利用α,β-不飽和酮製備3,5-雙取代-4,5- 二氫-1H-�@�t衍生物
一、前言…………………………………………..101
二、結果與討論…………………………………..102
三、實驗部分……………………………………..110
四、參考文獻……………………………………..126
第五章 1H-�@�t�F衍生物之抗生活性評估
一、前言…………………………………………..129
二、結果與討論…………………………………..131
三、實驗部分……………………………………..136
四、參考文獻……………………………………..142
結論 ……………………………………………….143
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15. Tien, H. J.; Yeh, M. Y.; Huang, C. Y.; J. Chin. Chem. Soc. 1985, 32, 461.
16. Yeh, M. Y.; Tien, H. J.; Fuchigami, T.; Nonaka, T. J. Chin. Chem. Soc. 1986, 33, 83.
17. Yeh, M. Y.; Chan, F. F.; Tien, H. J.; Fuchigami, T.; Nonaka, T. J. Chin. Chem. Soc. 1989, 36, 143.
18. Yeh, M. Y.; Pan, I. H.; Chuang, C. P.; Tien, H. J. J. Chin. Chem. Soc. 1988, 35, 443.
19. Yeh, M. Y.; Chu, W. C. J. Chin. Chem. Soc. 1988, 35, 451.
20. Shih, M. H.; Yeh, M. Y. J. Chin. Chem. Soc. 1990, 37, 71.
21. Shih, M. H.; Yeh, M. Y. J. Chin. Chem. Soc. 1992, 39, 163.
22. Shih, M. H.; Lu, L. H.; Yeh, M. Y. J. Chin. Chem. Soc. 2001, 48, 883.
23. Shih, M. H.; Her, K. H.; Yeh, M. Y. J. Chin. Chem. Soc. 2001, 48, 1143.
24. Stewart, F. H. C. Chem. Rev. 1964, 64, 129.
25. Ohta, M.; Kato, H. Non-Benzenoid Aromatics, I ; Academic Press: New York, 1969; pp 117-171.
26. Greco, C. V.; Tobias, J.; Kier, L. B. J. Heterocycl. Chem. 1967, 4, 160.
27. Kier, L. B.; Roche, E. B. J. Pharm. Sci. 1967, 56, 149.
28. Greco, C. V.; Nyberg, W. H.; Cheng, C. C. J. Med. Pharm. Chem. 1962, 5, 861.
29. Imashiro, Y.; Masuda, K. Japan Patent 1969, 6932411; Chem. Abstr. 1970, 72, 111482q.
30. Saito, Y.; Kamitani, T. Japan Patent 1970, 7021710; Chem. Abstr. 1970, 73, 87926k.
31. Masuda, K.; Okutani, T. Japan Patent 1970, 7020903; Chem. Abstr. 1970, 74, 87928n.
32. Satyanarayana, K.; Rao, M. N. A. J. Pharm. Sci. 1995, 84, 2, 263.
33. Tökés, A. L.; Janzsó, G. Synth. Commun. 1989, 19, 3159.
34. Gao, C.; Hay, A. S. Synth. Commun. 1995, 25, 1877.
35. Cho, H.; Ueda, M.; Ohnaka, Y.; Hayashimatsu, M. Heterocycles, 1984, 22, 1959.
36. Kambe, S.; Saito, K.; Kishi, H. Synthesis, 1979, 287.
37. García Navíc, J. L.; Lorente, A.; Soto, J. L. Heterocycles, 1982, 19, 305.

第四章 參考文獻:
1. Sachchar, S. P.; Singh, A. K. J. Indian Chem. Soc. 1985, 142.
2. Dambal, D. B.; Pattanashetti, P. P.; Tikare, R. K.; Badami, B. V.; Puranik, G. S. Indian J. Chem. 1984, 23B, 186.
3. Cremlyn, R. J.; Swinbourne, F. J.; Mookerjee, E. Indian J. Chem. 1986, 25B, 562.
4. Kulkarni, S. E.; Mane, R. A.; Ingle, D. B. Indian J. Chem. 1986, 25B, 452.
5. Gawande, N. G.; Shingare, M. S. Indian J. Chem. 1987, 26B, 351.
6. Thakare, V. G.; Wadodkar, K. N. Indian J. Chem. 1986, 25B, 610.
7. Srivastava, R. P.; Neelima; Bhaduri, A. P. Indian J. Chem. 1987, 26B, 418.
8. Tökés, A. L.; Janzsó, G. Synth. Commun. 1989, 19(18), 3159.
9. EL-Khawass, S. M.; Farghaly, A. M.; Chaaban, I.; Fahmy, S. M. J. Chin. Chem. Soc. 1990, 37, 605.
10. Gao, C.; Hay, A. S. Synth. Commun. 1995, 25(12), 1877.
11. Satyanarayana, K.; Rao, M. N. A. J. Pharm. Sci. 1995, 84, 263.
12. Satyanarayana, K.; Rao, M. N. A. Eur. J. Med. Chem. 1995, 30, 641.
13. Vishnu Vardhan Reddy, K.; Sampath Rao, P.; Ashok, D. Synth. Commun. 1998, 29, 2365.
14. Pinto, D. C. G. A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron, 1999, 55, 10187.
15. Müller, E.; Kálai, T.; Jekö, J.; Hideg, K. Synthesis, 2000, 10, 1415.
16. DeShong, P.; Soli, E. D.; Slough, G. A.; Sidler, D. R.; Elango, V.; Rybczynski, P. J.; Vosejpka, L. J. S.; Lessen, T. A.; Le, T. X.; Anderson, G. B.; von Philipsborn, W.; Vöhler, M.; Rentsch, D.; Zerbe, O. J. Organomet. Chem. 2000, 593, 49.
17. Holla, B. S.; Akberali, P. M.; Shivananda, M. K. IL Farmaco, 2000, 55, 256.
18. Ali, M. M.; Doshi, A. G.; Raghuwanshi, P. B. Synth. Commun. 2000, 30, 3241.
19. Pathak, V. N.; Pathak, R.; Gupta, R.; Oza, C. K. Synth. commun. 1997, 27, 1811.
20. Haunert, F.; Bolli, M. H.; Hinzen, B.; Ley, S. V. J. Chem. Soc. Perkin Trans. I. 1998, 15, 2235.
21. Bauer, U.; Egner, B. J.; Nilsson, I.; Berghult, M. Tetrahedron Lett. 2000, 41, 2713.
22. Kavali, J. R.; Badami, B. V. IL Farmaco, 2000, 55, 406.
23. Turnbull, K.; Sun, C.; Krein, D. M. Tetrahedron Lett. 1998, 39, 1509.
24. Turnbull, K.; Krein, D. M. Synthesis. 1996, 1183.
25. Marx, J. A.; Turnbull, K. Tetrahedron Lett. 1993, 34, 239.
26. Gelvin, C. R.; Turnbull, K. Helv.Chim. Acta. 1992, 75, 1931.
27. Burson, Ⅲ, W. C.; Jones, D. R.; Turnbull, K.; Preston, P. N. Synthesis. 1991, 745.
28. Turnbull, K.; Blackburn, T. L.; Esterline, D. T. J. Heterocycl. Chem. 1990, 27, 1259.
29. Fokas, D.; Ryan, W. J.; Casebier, D. S.; Coffen, D. L. Tetrahedron Lett. 1998, 39, 2235.
30. Powers, D. G.; Casebier, D. S.; Fokas, D.; Ryan, W. J. Troth, J. R.; Coffen, D. L. Tetrahedron, 1998, 54, 4085.
31. Yeh, M. Y.; Tien, H. J.; Huang, L. Y.; Chen, M. H. J. Chin. Chem. Soc. 1986, 30, 29.
32. Yeh, M. Y.; Tien, H. J.; Nonaka, T. J. Org. Chem. 1983, 48, 1382.
33. Chu, W. C.; Chan, F. F.; Yeh, M. Y. Hua-Hzueh 1988, 46, 181.
34. Yeh, M. Y.; Chu, W. C. J. Chin. Chem. Soc. 1988, 35, 451.
35. Yeh, M. Y.; Pan, I. H.; Chuang, C. P.; Tien, H. J. J. Chin. Chem. Soc. 1988, 35, 443.
36. Shih, M. H.; Yeh, M. Y. J. Chin. Chem. Soc. 1990, 37, 71.
37. Shih, M. H.; Yeh, M. Y. J. Chin. Chem. Soc. 1992, 39, 163.
38. Shih, M. H.; Her, K. H.; Yeh, M. Y. J. Chin. Chem. Soc. 2001, 48, 1143.

第五章 參考文獻:
1. Sachchar, S. P.; Singh, A. K. J. Indian Chem. Soc. 1985, 142.
2. Dambal, D. B.; Pattanashetti, P. P.; Tikare, R. K.; Badami, B. V.; Puranik, G. S. Indian J. Chem. 1984, 23B, 186.
3. Cremlyn, R. J.; Swinbourne, F. J.; Mookerjee, E. Indian J. Chem. 1986, 25B, 562.
4. Kulkarni, S. E.; Mane, R. A.; Ingle, D. B. Indian J. Chem. 1986, 25B, 452.
5. Gawande, N. G.; Shingare, M. S. Indian J. Chem. 1987, 26B, 351.
6. Holla, B. S.; Akberali, P. M.; Shivananda, M. K. IL Farmaco, 2000, 55, 256.
7. Satyanarayana, K.; Rao, M. N. A. J. Pharm. Sci. 1995, 84, 263.
8. Satyanarayana, K.; Rao, M. N. A. Eur. J. Med. Chem. 1995, 30, 641.
9. Gao, C.; Hay, A. S. Synth. Commun. 1995, 25(12), 1877.
10. Vishnu Vardhan Reddy, K.; Sampath Rao, P.; Ashok, D. Synth. Commun. 1998, 29, 2365.
11. Pinto, D. C. G. A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron, 1999, 55, 10187.
12. Ali, M. M.; Doshi, A. G.; Raghuwanshi, P. B. Synth. Commun. 2000, 30, 3241
13. Kavali, J. R.; Badami, B. V. IL Farmaco, 2000, 55, 406.
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