绿原酸的结构修饰研究
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摘要
绿原酸存在于多种植物中,具有广泛的药理作用,近年来对绿原酸的研究发展较快,目前研究表明绿原酸口服吸收率低,在血浆中主要以代谢产物的形式存在,主要通过肾脏排泄,具有抗氧化,抗肿瘤,抗菌,抗病毒,免疫调节,降糖等多种作用,对绿原酸的深入研究,将为我们科学制药与合理用药提供重要的理论依据,本文主要尝试分三个思路对绿原酸进行修饰,以期有更好的药理活性。
首先论述了绿原酸的分布、药理活性和研究进展,对其结构单元咖啡酸和奎尼酸也做了简单介绍；接着我们对绿原酸奎尼结构单元进行修饰,希望合成达菲类似物,主要尝试了C1-羟基消除反应和C3-酯基的水解反应,以及C4、C5-羟基的氨化反应和氧化反应；最后则是对羧基官能团进行修饰,包括了羧基的还原和酰胺化反应；第五、六章主要是对实验工作的总结和展望以及相关化合物的具体实验步骤和图谱数据。
本文中化合物的结构均通过核磁共振谱的分析得到确认。
Chlorogenic acid found in many plants, with widespread pharmacological actives. In recent years, research on chlorogenic acid has developed rapidly. Current studies show that chlorogenic acid has a low oral absorption rate in vivo and exists in plasma mainly in the form of metabolites, it mainly excreted through the kidneys.
Chlorogenic acid shows many functions such as antioxidant, antitumor, antibacterial, antiviral, immune adjustment, hypoglycemic, etc. This thesis reported the structure modification on chlorogenic acid in order to find structure with better pharmacological activities. The futher study on chlorogenic acid to provide theoretical basis about scientific pharmaceutical and rationally drug design for us.
The paper reviews the structure of chlorogenic acid and its analogues in the research progress and pharmacological activity, as well as its structure unit qunny acid and caffeic acid are also discussed. In chapterⅡandⅢwe expected to synthesis the Tamiflu analogues structure by modifying the chologenic acid. we tried to eliminate the hydroxyl of C1, hydrolysis esters base of C3, oxidate and aminate the hydroxyl of C4 and C5, qunny unit is also useful starting materials as chiral source for the syntheses. ChapterⅣis about carboxyl functional groups modification, which is divided into two parts, including the carboxyl reduction and amidation reactions.
The summary and prospect of our research work was described in chapterⅤand the spectrogram data and specific experiment process of the related compounds in this thesis were described in chapterⅥ.
The structures of compounds in this thesis were identified by NMR spectrogram.
首先论述了绿原酸的分布、药理活性和研究进展,对其结构单元咖啡酸和奎尼酸也做了简单介绍；接着我们对绿原酸奎尼结构单元进行修饰,希望合成达菲类似物,主要尝试了C1-羟基消除反应和C3-酯基的水解反应,以及C4、C5-羟基的氨化反应和氧化反应；最后则是对羧基官能团进行修饰,包括了羧基的还原和酰胺化反应；第五、六章主要是对实验工作的总结和展望以及相关化合物的具体实验步骤和图谱数据。
本文中化合物的结构均通过核磁共振谱的分析得到确认。
Chlorogenic acid found in many plants, with widespread pharmacological actives. In recent years, research on chlorogenic acid has developed rapidly. Current studies show that chlorogenic acid has a low oral absorption rate in vivo and exists in plasma mainly in the form of metabolites, it mainly excreted through the kidneys.
Chlorogenic acid shows many functions such as antioxidant, antitumor, antibacterial, antiviral, immune adjustment, hypoglycemic, etc. This thesis reported the structure modification on chlorogenic acid in order to find structure with better pharmacological activities. The futher study on chlorogenic acid to provide theoretical basis about scientific pharmaceutical and rationally drug design for us.
The paper reviews the structure of chlorogenic acid and its analogues in the research progress and pharmacological activity, as well as its structure unit qunny acid and caffeic acid are also discussed. In chapterⅡandⅢwe expected to synthesis the Tamiflu analogues structure by modifying the chologenic acid. we tried to eliminate the hydroxyl of C1, hydrolysis esters base of C3, oxidate and aminate the hydroxyl of C4 and C5, qunny unit is also useful starting materials as chiral source for the syntheses. ChapterⅣis about carboxyl functional groups modification, which is divided into two parts, including the carboxyl reduction and amidation reactions.
The summary and prospect of our research work was described in chapterⅤand the spectrogram data and specific experiment process of the related compounds in this thesis were described in chapterⅥ.
The structures of compounds in this thesis were identified by NMR spectrogram.
引文
[1]赵昱,赵军,李湘萍,等.咖啡酰奎尼酸类化合物研究进展[J].中国中药杂志,2006,32(11)：869.
[2]Nair V.HIV integrase as a target for antiviral chemothe-rapy [J]. Rev Med Virol, 2002:12(3):179-193.
[3](a)白威,田敏卿,马亚平,等.HIV-1整合酶抑制剂研究进展[J].中国艾滋病,2006,12(1)：81-83.(b)但飞君,董俊兴.HIV-1整合酶及其抑制剂研究进展[J].解放军药学,2004,20(2)：122-126.(c)姜晓华,龙亚秋.结构多样的HIV-1整合酶抑制剂：过去、现在、未来[J].有机化学,2004,24(11)：1380-1388.
[4]闻平,张清波,张树杰.HPLC法测定忍冬藤中绿原酸含量[J].中国药品标准,2002,3(4)：47/48
[5]Cyrr Genet.2003 May;43(2):103-11. Epub 2003 Mar 14. Related Articles, Links Quinic acid induces hypovirulence and expression of a hypovirulence-associated double-stranded RNA in Rhizoctonia solani. Liu C, Lakshman DK. Tavantzis SM.
[6]Huang M, Richards W G, Grant G H. Diketoacid HIV-1 integrase inhibitors:An ab initio study [J]. JPhys Chem A,2005,109(23):5198-5202.
[7]Mohamed A Awad, Anton de Jager, Lucie M van Westing. Flavonoid and chlorogenic acid levels in apple fruit:characterisation of variation[J]. Scientia Horticithurae,2000, 83(3):249-263.
[8]Planla Med.2001 Jun;67(4):322-5. Studies on the hepatocyte protective activity and the structure-activity relationships of quinic acid and caffeic acid derivatives from the flower buds of Lonicera bournei. Xiang T, Xiong QB, Ketut AI, Tezuka Y, Nagaoka T, Wu LJ, Kadota S. Department of Natural Medicine, Shenyang Pharmaceutical University, Shenyang, People's Republic of China.
[9]Charles J Sih, et al. Separation and synthesis of pinoresinol diglucoside moide olive J Am Chem Soc,1976,98(17):5412.
[10]Int J Biol Macromol.2000 Jun 13;27(3):219-28. Thermodynamics of interaction of caffeic acid and quinic acid with multisubunit proteins.Suryaprakash P, Kumar RP, Prakash V.Department of Protein Chemistry and Technology, Central Food Technological Research Institute,570013, Mysore, India.
[11]Young S D. L-870,810:discovery of a potent HIV integrase inhibitor with potential clinical utility [C]. XIV International AIDS Conference, Barcelona, abstract LbpEA 9007, 2002.
[12]Pommier Y, Marchand C, Neamati N. Retroviral integrase inhibitors year 2000:update and perspectives [J].Antiviral Res,2000,47(3):139-148.
[13]Raveendra D, Tino S, Omoshile C, et al. β-Diketo acid pharmacophore hypothesis.1. Discovery of a Novel Class of HIV-1 Integrase Inhibitors [J]. J Med Chem,2005, 48(1):111-120.
[14]Hazuda D J, Peter F, Marc W, et al. Inhibitors of strand transfer that prevent integration and inhibit HIV-1 replicatoion in cells [J]. Science,2000,287(5453):646-650.
[15]Maurin C, Bailly F, Cotelle P. Structure-activity relationships of HIV-1 integrase inhibitors-enzyme-ligand interactions [J]. Curr Med Chem,2003,10(18):1795-1810.
[16]Zhuang L H, Wai J S, Embrey M W, et al. Design and synthesis of 8-hydroxy-[1,6] naphthyridines as novel inhibitors of HIV-1 integrase in vitro and in infected cells [J]. J Med Chem,2003,46(4):453-456.
[17]Hazduda D J, Steve D Y, Guare J P, et al. Integrase inhibitors and celluar immunity suppress retroviral replication in rhesus macaques [J]. Science,2004,305(5683):528-532.
[18]Krajewski K, Marchand C. Long Y Q. et al. Synthesis and HIV-1 integrase inhibitory activity of dimeric and tetrameric analogs indolicidin [J]. Bioorg Med Chem Lett,2004, 14(22):5595-5598.
[19]De-Soultrait V R. A novel short peptide is a specific inhibitor of the human immon-odeficiency virus type 1 integrase [J]. J Mol Biol,2002,318(1):45-48.
[20]Singh S B. Integramides A and B, two novel non-ibosomal linear peptides containing nine C(alpha)-methyl amino acids produced by fungal fermentations that are inh- ibitors of HIV-1 integrase [J]. Org Lett,2002:4(9):1431-1434.
[21]Fermandjian S, Self-association of an amphipathic helix peptide inhibitor of HIV-1 integrase assessed by electro spray ionization mass spectrometry in trifluor oethanol/water mixtures [J]. Rapid Commun Mass Spectrom,2001,15(5):320-324.
[22]Robison W E, Reinecke M G, Abde-Malek S, et al. Inhibitors of HIV-1 replication that inhibit HIV integrase [J]. Proc Natl Acad Sci,1996,93(13):6326-6331.
[23]Xu Y W, Zhao G S, Shin C G, et al. Caffeoyl naphthalenesulfonamide derivatives as HIV integrase inhibitors [J]. Bioorg Med Chem,2003,11(17):3589-3593.
[24]Billich A. S-1360 Shionogi-GlaxoSmitKline [J]. Curr Opin Invest Drugs,2003,4(2) :206-209.
[25]Lataillade M, Kozal M J. The hunt for HIV-1 integrase inhibitors [J]. AIDS Patient Care STDS,2006,20(7):489-501.
[26]Van-BREE j b. DE-Boer A G. Danhof M Characterization of an "in vitro" blood-brain barrier:effects of molecular size and lipophilicity on cerebrovascular endothelial thansport rates of drugs 1988(3).
[27]高木满茶提取液中的奎尼酸含量已经提取特性[期刊论文]-福建茶叶2002.
[28]滕荣伟.周志宏.王德祖. 白花刺参中的咖啡酰奎尼酸成分[期刊论文]--波普学杂志2002(02).
[29]Gongore L. Giner RM. M ANEZ s Effects of caffeoyl conjugates of isoprenyl hydroquinone gluc oside and quinic on leukocyte function [外文期刊] 2000 (21)
[30]Pirjo Mattila, Jarkko HeHstrom. Phenolic acids in potatoes, vegetables, and some of their products[J].Journal of Food Composition and Analysis,2006,19(3):205/211.
[31]H. Inouye, S. Saito, and T. Shingu. Tetrahedron Lett.,1970,3581; H. Inouye, Y.Takeda, S. Saito, H. Nishimura, and R.Sakuragi, Yakugaku Zasshi,1974,94,577.
[32]F. L. Austin and I. A. Wolff, J. Agric. FoodChem.,1968,16,133; J. Cores and D. C. Patterson, Phytochemistry,8,203 (1969).
[33]J. Boeckmann, G. Schill, Chem. Ber,1911,110,703.
[34](a) A. P. Bashall, J. F. Collins, Tetrahedron Lett.1975,16,3489; (b) M. G. Cabiddu, E. Cadoni, S. De Montis, et al, Tetrahedron,2003,59,4383; (c) E. J. Vanden, I. Mailleux, Synth. Commun.2001,31,1.
[35](a) J. H. ClarK, H. L. Holland, J. M. Miller, Tetrahedron Lett.1976,17,3361; (b) R. E. Zelle, W. J. McClellan, Tetrahedron Lett.1991,32,2461; (c) T. Geller, J. Jakupovic, H. G. S. Chmalz, Tetrahedron Lett.1998,39,1541; (d) X. Ariza, O. Pineda, J. Vilarrase, et al, Org. Lett.2001,3,1399.
[36]K. Ogura, G.I. Tsuchihashi, Tetrahedron Lett.1971,12,3151.
[37](a) Fatiadi A J. Synthesis,1976,65:133; (b) Pizey J S. Synthetic Peagents. Vol.2. New York:Halsted Press,1974.143-147; (c) Attenburrow J, et al. J. Chem. Soc.,1952:1104; (d) Goldman I M. J. Org. Chem.,1969,34:1979.
[38](a) S. C. Chaudary, O. Hermandez, Tetrahedron Lett.1979,99; (b) C. Reese,Q. Wu, J. Org. Biomol. Chem.2003,1,3160; (c) Q. Wu, Y. Wang, W. Chen, et al, Lett. Org. Chem.2005,. 13.
[39]M. Harada, N. Tenmyo, M. Aburada, and T. Endo, Yakngaku Zasshi,1974,94.157; M. Aburada, Y. Shibata, and M. Harada, J. Pharmacobio-Dyn.,1978,1,81.
[40]J. B. Summers, H. Mazdiyasi, J. H. Holms, J. D. Ratajcxyk, R. D. Dyer, and G. W. Caryer, J. Med, Chem.,1987,30,574.
[41]J.Org.Chem.1991,62,7319-7323.
[42]邢其毅,裴伟伟等编著,基础有机化学上册,高等教育出版社3版,2005.
[43]Aggarwal, Varinder K, Sheldon, Chris G, Macdonald, Gregor J, Martin, William P,Journal of the American Chemical Society,2002, vol.124,335p.10300-10301.
[44](a) Hnynes R K, et al. Aust. J. Chem.1982,35,517; (b) Hrubiec R T, Smith M B. J. Org. Chem.1984,49,431.
[45](a) Bose A K. Lal B. Tetrahedron Lett.1973,40:3937; (b) Osamu S, Miko M, et al. Tetrahedron Lett.1999,40(42):7477.
[46]Macdonald, Gregor J, Martin, J. Org. Chem.2003.68.2175-2182.
[47]Smith M B. J. Org. Chem,2008,73,6.
[48]K. C. Nicolaou, K. R. Reddy, G. Shokotas, et al, J. Am. Chem. Soc.1993,115,3558.
[49](a) K. Tanemura, T. Suzuki, T. Horaguchi, Bull. Chem. Soc. Jpn.1994,67,290; (b) T. Kametani, H. Kondoh, T. Honda, et al, Chem. Lett.1989,901; (c) G. Maiti, S. C. Roy, J. Org. Chem.1996,61,6038; (d) Y.-H. Chen, Y.-T. Tseng, T.-Y.Luh, J. Chem. Soc., Chem. Commun.1996,327; (e) S. S. Elmorsy, M. V. Bhatt, A. Pelter, Tetrahedron Lett.1992,33, 1657; (f) M. N. Rao, P. Kumar, A. P. Singh, et al, Synth. Commun.1992,22,1299; (g) S. Hoyer, P. Laszlo, Synthesis 1986,655; (h) J. Otera, H. Nozaki, Tetrahedron Lett.1986,27, 5743; (i) G. M. Coppola, Synthesis 1984,1021.
[50](a) L. D. Arnold, T. H. Kalantar, J. C. Vederas, J. Am. Chem. Soc.1985,107,7105; (b) L. D. Arnold, R. G. May, J. C. Vederas, J. Am. Chem. Soc.1988,110,2237.
[2]Nair V.HIV integrase as a target for antiviral chemothe-rapy [J]. Rev Med Virol, 2002:12(3):179-193.
[3](a)白威,田敏卿,马亚平,等.HIV-1整合酶抑制剂研究进展[J].中国艾滋病,2006,12(1)：81-83.(b)但飞君,董俊兴.HIV-1整合酶及其抑制剂研究进展[J].解放军药学,2004,20(2)：122-126.(c)姜晓华,龙亚秋.结构多样的HIV-1整合酶抑制剂：过去、现在、未来[J].有机化学,2004,24(11)：1380-1388.
[4]闻平,张清波,张树杰.HPLC法测定忍冬藤中绿原酸含量[J].中国药品标准,2002,3(4)：47/48
[5]Cyrr Genet.2003 May;43(2):103-11. Epub 2003 Mar 14. Related Articles, Links Quinic acid induces hypovirulence and expression of a hypovirulence-associated double-stranded RNA in Rhizoctonia solani. Liu C, Lakshman DK. Tavantzis SM.
[6]Huang M, Richards W G, Grant G H. Diketoacid HIV-1 integrase inhibitors:An ab initio study [J]. JPhys Chem A,2005,109(23):5198-5202.
[7]Mohamed A Awad, Anton de Jager, Lucie M van Westing. Flavonoid and chlorogenic acid levels in apple fruit:characterisation of variation[J]. Scientia Horticithurae,2000, 83(3):249-263.
[8]Planla Med.2001 Jun;67(4):322-5. Studies on the hepatocyte protective activity and the structure-activity relationships of quinic acid and caffeic acid derivatives from the flower buds of Lonicera bournei. Xiang T, Xiong QB, Ketut AI, Tezuka Y, Nagaoka T, Wu LJ, Kadota S. Department of Natural Medicine, Shenyang Pharmaceutical University, Shenyang, People's Republic of China.
[9]Charles J Sih, et al. Separation and synthesis of pinoresinol diglucoside moide olive J Am Chem Soc,1976,98(17):5412.
[10]Int J Biol Macromol.2000 Jun 13;27(3):219-28. Thermodynamics of interaction of caffeic acid and quinic acid with multisubunit proteins.Suryaprakash P, Kumar RP, Prakash V.Department of Protein Chemistry and Technology, Central Food Technological Research Institute,570013, Mysore, India.
[11]Young S D. L-870,810:discovery of a potent HIV integrase inhibitor with potential clinical utility [C]. XIV International AIDS Conference, Barcelona, abstract LbpEA 9007, 2002.
[12]Pommier Y, Marchand C, Neamati N. Retroviral integrase inhibitors year 2000:update and perspectives [J].Antiviral Res,2000,47(3):139-148.
[13]Raveendra D, Tino S, Omoshile C, et al. β-Diketo acid pharmacophore hypothesis.1. Discovery of a Novel Class of HIV-1 Integrase Inhibitors [J]. J Med Chem,2005, 48(1):111-120.
[14]Hazuda D J, Peter F, Marc W, et al. Inhibitors of strand transfer that prevent integration and inhibit HIV-1 replicatoion in cells [J]. Science,2000,287(5453):646-650.
[15]Maurin C, Bailly F, Cotelle P. Structure-activity relationships of HIV-1 integrase inhibitors-enzyme-ligand interactions [J]. Curr Med Chem,2003,10(18):1795-1810.
[16]Zhuang L H, Wai J S, Embrey M W, et al. Design and synthesis of 8-hydroxy-[1,6] naphthyridines as novel inhibitors of HIV-1 integrase in vitro and in infected cells [J]. J Med Chem,2003,46(4):453-456.
[17]Hazduda D J, Steve D Y, Guare J P, et al. Integrase inhibitors and celluar immunity suppress retroviral replication in rhesus macaques [J]. Science,2004,305(5683):528-532.
[18]Krajewski K, Marchand C. Long Y Q. et al. Synthesis and HIV-1 integrase inhibitory activity of dimeric and tetrameric analogs indolicidin [J]. Bioorg Med Chem Lett,2004, 14(22):5595-5598.
[19]De-Soultrait V R. A novel short peptide is a specific inhibitor of the human immon-odeficiency virus type 1 integrase [J]. J Mol Biol,2002,318(1):45-48.
[20]Singh S B. Integramides A and B, two novel non-ibosomal linear peptides containing nine C(alpha)-methyl amino acids produced by fungal fermentations that are inh- ibitors of HIV-1 integrase [J]. Org Lett,2002:4(9):1431-1434.
[21]Fermandjian S, Self-association of an amphipathic helix peptide inhibitor of HIV-1 integrase assessed by electro spray ionization mass spectrometry in trifluor oethanol/water mixtures [J]. Rapid Commun Mass Spectrom,2001,15(5):320-324.
[22]Robison W E, Reinecke M G, Abde-Malek S, et al. Inhibitors of HIV-1 replication that inhibit HIV integrase [J]. Proc Natl Acad Sci,1996,93(13):6326-6331.
[23]Xu Y W, Zhao G S, Shin C G, et al. Caffeoyl naphthalenesulfonamide derivatives as HIV integrase inhibitors [J]. Bioorg Med Chem,2003,11(17):3589-3593.
[24]Billich A. S-1360 Shionogi-GlaxoSmitKline [J]. Curr Opin Invest Drugs,2003,4(2) :206-209.
[25]Lataillade M, Kozal M J. The hunt for HIV-1 integrase inhibitors [J]. AIDS Patient Care STDS,2006,20(7):489-501.
[26]Van-BREE j b. DE-Boer A G. Danhof M Characterization of an "in vitro" blood-brain barrier:effects of molecular size and lipophilicity on cerebrovascular endothelial thansport rates of drugs 1988(3).
[27]高木满茶提取液中的奎尼酸含量已经提取特性[期刊论文]-福建茶叶2002.
[28]滕荣伟.周志宏.王德祖. 白花刺参中的咖啡酰奎尼酸成分[期刊论文]--波普学杂志2002(02).
[29]Gongore L. Giner RM. M ANEZ s Effects of caffeoyl conjugates of isoprenyl hydroquinone gluc oside and quinic on leukocyte function [外文期刊] 2000 (21)
[30]Pirjo Mattila, Jarkko HeHstrom. Phenolic acids in potatoes, vegetables, and some of their products[J].Journal of Food Composition and Analysis,2006,19(3):205/211.
[31]H. Inouye, S. Saito, and T. Shingu. Tetrahedron Lett.,1970,3581; H. Inouye, Y.Takeda, S. Saito, H. Nishimura, and R.Sakuragi, Yakugaku Zasshi,1974,94,577.
[32]F. L. Austin and I. A. Wolff, J. Agric. FoodChem.,1968,16,133; J. Cores and D. C. Patterson, Phytochemistry,8,203 (1969).
[33]J. Boeckmann, G. Schill, Chem. Ber,1911,110,703.
[34](a) A. P. Bashall, J. F. Collins, Tetrahedron Lett.1975,16,3489; (b) M. G. Cabiddu, E. Cadoni, S. De Montis, et al, Tetrahedron,2003,59,4383; (c) E. J. Vanden, I. Mailleux, Synth. Commun.2001,31,1.
[35](a) J. H. ClarK, H. L. Holland, J. M. Miller, Tetrahedron Lett.1976,17,3361; (b) R. E. Zelle, W. J. McClellan, Tetrahedron Lett.1991,32,2461; (c) T. Geller, J. Jakupovic, H. G. S. Chmalz, Tetrahedron Lett.1998,39,1541; (d) X. Ariza, O. Pineda, J. Vilarrase, et al, Org. Lett.2001,3,1399.
[36]K. Ogura, G.I. Tsuchihashi, Tetrahedron Lett.1971,12,3151.
[37](a) Fatiadi A J. Synthesis,1976,65:133; (b) Pizey J S. Synthetic Peagents. Vol.2. New York:Halsted Press,1974.143-147; (c) Attenburrow J, et al. J. Chem. Soc.,1952:1104; (d) Goldman I M. J. Org. Chem.,1969,34:1979.
[38](a) S. C. Chaudary, O. Hermandez, Tetrahedron Lett.1979,99; (b) C. Reese,Q. Wu, J. Org. Biomol. Chem.2003,1,3160; (c) Q. Wu, Y. Wang, W. Chen, et al, Lett. Org. Chem.2005,. 13.
[39]M. Harada, N. Tenmyo, M. Aburada, and T. Endo, Yakngaku Zasshi,1974,94.157; M. Aburada, Y. Shibata, and M. Harada, J. Pharmacobio-Dyn.,1978,1,81.
[40]J. B. Summers, H. Mazdiyasi, J. H. Holms, J. D. Ratajcxyk, R. D. Dyer, and G. W. Caryer, J. Med, Chem.,1987,30,574.
[41]J.Org.Chem.1991,62,7319-7323.
[42]邢其毅,裴伟伟等编著,基础有机化学上册,高等教育出版社3版,2005.
[43]Aggarwal, Varinder K, Sheldon, Chris G, Macdonald, Gregor J, Martin, William P,Journal of the American Chemical Society,2002, vol.124,335p.10300-10301.
[44](a) Hnynes R K, et al. Aust. J. Chem.1982,35,517; (b) Hrubiec R T, Smith M B. J. Org. Chem.1984,49,431.
[45](a) Bose A K. Lal B. Tetrahedron Lett.1973,40:3937; (b) Osamu S, Miko M, et al. Tetrahedron Lett.1999,40(42):7477.
[46]Macdonald, Gregor J, Martin, J. Org. Chem.2003.68.2175-2182.
[47]Smith M B. J. Org. Chem,2008,73,6.
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