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Progress in Chemistry 2018, Vol. 30 Issue (5): 586-600 DOI: 10.7536/PC171248 Previous Articles   Next Articles

Special Issue: 酶化学

• Review •

Synthesis and Glycosidase Inhibitory Activities of Fluorinated Iminosugars

Yixian Li1,2*, Yuemei Jia1,2, Chuyi Yu1,2,3*   

  1. 1. CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;
    2. University of Chinese Academy of Sciences, Beijing 100049, China;
    3. National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, China
  • Received: Revised: Online: Published:
  • Supported by:
    The work was supported by the National Natural Science Foundation of China (No. 21772206, 21642012).
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Iminosugars have shown great potential in pharmaceutical industry due to their potent glycosidase inhibition, anti-virus and anti-cancer activities. Systematic study of structure-activity relationship of iminosugars will help to develop highly active and selective lead compounds. Fluorination is usually the most used method of studying structure-activity relationship. This review summarized the reported synthetic strategies of fluorinated iminosugars and the related glycosidase inhibitory activities. The synthetic strategies are roughly categorized to three types, namely, fluorine containing building blocks, fluorinated sugars and fluorinating reagents, and each of them is reviewed with merits, disadvantages and its application. The structure-activity relationship of some representative iminosugars is then preliminarily concluded based on the reported glycosidase inhibitory activities of fluorinated iminosugars. Intact iminosugar ring is believed important for interaction with enzymes, while fluorination of side chain and the fused ring would influence inhibitory spectrum and potency, respectively. Therefore, the current research results of fluorinated iminosugars have made important contributions to iminosugar chemistry. With fluorine as tool, the structure-activity relationship of iminosugars can be further completed and corrected in the future, and therefore would certainly help to provide profound foundation for the design and syntheses of iminosugars with potential medicinal values, and thus effectively promote the related drug discovery.
Contents
1 Iminosugar and its application
2 Synthetic strategies of fluorinated iminosugars and related biological activity study
2.1 Synthesis of fluorinated iminosugars from fluorinated building blocks
2.2 Synthesis of fluorinated iminosugars from fluorinated sugars
2.3 Synthesis of fluorinated iminosugars by subsequent introduction of fluorine
3 Fluorination in structure-activity relationship study of iminosugars
Key words: iminosugar, azasugar, fluorination, glycosidase inhibition, structure-activity relationship

CLC Number: 

[1] Butters T D, Dwek R A, Platt F M. Chem. Rev., 2000, 100:4683.
[2] Wong C H, Dumas D P, Ichikawa Y, Koseki K, Danishefsky S J, Weston B W, Lower J B. J. Am Chem. Soc., 1992, 114:7321.
[3] Compain P, Martin O R. Curr. Top. Med. Chem., 2003, 3:541.
[4] Bols M, Hazelle R, Thomsen I B. Chem. Eur. J., 1997, 3:940.
[5] Somsak L, Nagy V, Hadady Z, Docsa T, Gergely P. Curr. Pharm. Des., 2003, 9:1177.
[6] Moriyama H, Tsukida T, Inoue Y, Yokota K, Yoshino K, Kondo H, Miura N, Nishimura S I. J. Med. Chem., 2004, 47:1930.
[7] Lee R E, Smith M D, Nash R J, Griffiths R C, McNeil M, Grewal R K, Yan W, Besra G S, Brennan P J, Fleet G W J. Tetrahedron Lett., 1997, 38:6733.
[8] Liautard V, Desvergnes V, Itoh K, Liu H W, Martin O R. J. Org. Chem., 2008, 73:3103.
[9] Davis B G. Tetrahedron:Asymmetry, 2009, 20:652.
[10] Asano N. Cell. Mol. Life Sci., 2009, 66:1479.
[11] Nash R J, Kato A, Yu C Y, Fleet G W J. Future Med. Chem., 2011, 3:1513.
[12] Horne G, Wilson F X, Tinsley J, Williams D H, Storer R. Drug Discov. Today, 2011, 16:107.
[13] Allan G, Ouadid-Ahidouch H, Sanchez-Fernandez E M, Risquez-Cuadro R, Garcia Fernandez J M, Ortiz-Mellet C, Ahidouch A. Plos One, 2013, 8:e76411.
[14] Sanchez-Fernandez E M, Risquez-Cuadro R, Chasseraud M, Ahidouch A, Mellet C O, Ouadid-Ahidouch H, Fernandez J M G. Chem. Commun., 2010, 46:5328.
[15] Wojtowicz K, Januchowski R, Sosinska P, Nowicki M, Zabel M. Oncology Reports, 2016, 35:2896.
[16] Dowall S D, Bewley K, Watson R J, Vasan S S, Ghosh C, Konai M M, Gausdal G, Lorens J B, Long J, Barclay W, Garcia-Dorival I, Hiscox J, Bosworth A, Taylor I, Easterbrook L, Pitman J, Summers S, Chan-Pensley J, Funnell S, Vipond J, Charlton S, Haldar J, Hewson R, Carroll M W. Viruses-Basel, 2016, 8:277.
[17] De Bruijne J, Weegink C J, Jansen P L M, Reesink H W. Vox Sang., 2009, 97:1.
[18] Hong Y P, Chen C, Guo W Y, Zhao L, Mei F C, Xiang M W, Wang W X. Arch. Med. Res., 2016, 47:436.
[19] Adrian H, David C, Ma C, Paul T. Immunol. Cell Biol., 2015, 93:A10.
[20] Hibberd A D, Clark D A, Trevillian P R, McElduff P. World J. Transplant., 2016, 6:206.
[21] Luan Z, Higaki K, Aguilar-Moncayo M, Ninomiya H, Ohno K, Isabel Garcia-Moreno M, Ortiz Mellet C, Garcia Fernandez J M, Suzuki Y. Chembiochem, 2009, 10:2780.
[22] Li Z H, Li T H, Dai S X, Xie X L, Ma X P, Zhao W, Zhang W M, Li J, Wang P G. ChemBioChem, 2013, 14:1239.
[23] Boyd R E, Lee G, Rybczynski P, Benjamin E R, Khanna R, Wustman B A, Valenzano K J. J. Med. Chem., 2013, 56:2705.
[24] Whitby K, Pierson T C, Geiss B, Lane K, Engle M, Zhou Y, Doms R W, Diamond M S. J. Virol., 2005, 79:8698.
[25] Whitby K, Taylor D, Patel D, Ahmed P, Tyms A S. Antivir. Chem. Chemother., 2004, 15:141.
[26] Rathore A P S, Paradkar P N, Watanabe S, Tan K H, Sung C, Connolly J E, Low J, Ooi E E, Vasudevan S G. Antivir. Res., 2011, 92:453.
[27] Watanabe S, Rathore A P S, Sung C, Lu F, Khoo Y M, Connolly J, Low J, Ooi E E, Lee H S, Vasudevan S G. Antivir. Res., 2012, 96:32.
[28] Sung C, Wei Y, Watanabe S, Lee H S, Khoo Y M, Fan L, Rathore A P S, Chan K W K, Choy M M, Kamaraj U S, Sessions O M, Aw P, de Sessions P F, Lee B, Connolly J E, Hibberd M L, Vijaykrishna D, Wijaya L, Ooi E E, Low J G H, Vasudevan S G. Plos Neglet. Trop. D., 2016, 10:e0004851.
[29] Yoshida E, Kunimoto D, Lee S S, Sherman M, Heathcote J, Enns R. Gastroenterology, 2006, 130:A784.
[30] Kaita K, Yoshida E, Kunimoto D, Anderson F, Morris S, Marotta P, Scully L, Peltekian K, Enns R, Diaz-Mitoma F, Lee S, Worobetz L, Pankovich J, Petersen A K. J. Hepatol., 2007, 46:S56.
[31] Chen L, Lu J, Huang T, Yin J, Wei L, Cai Y D. Plos One, 2014, 9:e107767.
[32] Taylor D L, Sunkara P S, Liu P S, Kang M S, Bowlin T L, Tyms A S. AIDS, 1991, 5:693.
[33] Taylor D L, Kang M S, Brennan T M, Bridges C G, Sunkara P S, Tyms A S. Antimicrob. Agents Chemother., 1994, 38:1780.
[34] Compain P, Martin O R. Iminosugars:From Synthesis to Therapeutic Applications, 1st ed. New York:Wiley-VCH, 2007.
[35] Mehta A, Zitzmann N, Rudd P M, Bock T M, Dwek R A. FEBS Lett., 1998, 430:17.
[36] Overkleeft H S, Renkema G H, Neele J, Vianello P, Hung I O, Strijland A, van der Burg A M, Koomen G J, Pandit U K, Aerts J M F G. J. Biol. Chem., 1998, 273:26522.
[37] Zitzmann N, Mehta A S, Carrouée S, Butters T D, Platt F M, McCauley J, Blumberg B S, Dwek R A, Block T M. Proc. Nat. Acad. Sci. USA, 1999, 96:11878.
[38] Li Q, Ye X S. Isr J. Chem., 2015, 55:336.
[39] Li X L, Zhu Z G, Duan K F, Chen H, Li Z W, Li Z, Zhang P Z. Tetrahedron, 2009, 65:2322.
[40] Godin G, Compain P, Masson G, Martin O R, keda K, Yu L, Asano N. Bioorg. Med. Chem. Lett., 2004, 14:5991.
[41] Yu L, Ikeda K, Kato A, Adachi I, Godin G, Compain P, Martin O R, Asano N. Bioorg. Med. Chem., 2006, 14:7736.
[42] Jakobsen P, Lundbeck J M, Kristiansen M, Breinholt J, Demuth H, Pawlas J, Torres Candela M P, Andersen B, Westergaard N, Lundgren K, Asano N. Bioorg. Med. Chem., 2001, 9:733.
[43] Miles R W, Tyler P C, Furneaux R H, Bagdassarian C K, Schramm V L. Biochemistry, 1998, 37:8615.
[44] Lewandowicz A, Tyler P C, Evans G B, Furneaux R H, Schramm V L. J. Biol. Chem., 2003, 278:31465.
[45] Wang D, Li Y H, Wang Y P, Gao R M, Zhang L H, Ye X S. Bioorg. Med. Chem., 2011, 19:41.
[46] Li X L, Qin Z B, Wang R, Chen H, Zhang P Z. Tetrahedron, 2011, 67:1792.
[47] Begue J P, Bonnet-Delpon D. Actualite Chimique, 2006, 83.
[48] Ojima I, Fluorine in Medicinal Chemistry and Chemical Biology, 1st ed. Wiley-Blackwell:Chichester, 2009.
[49] 李意羡(Li Y X). 中国科学院研究生院博士学位论文(Doctoral Dissertation of the Graduate University of Chinese Academy of Sciences), 2011.
[50] Fustero S, Simón-Fuentes A, Barrio P, Haufe G. Chem. Rev., 2015, 115:871.
[51] Ni C F, Hu M Y, Hu J B. Chem. Rev., 2015, 115:765.
[52] Kajimoto T, Liu K K C, Pederson R L, Zhong Z, Ichikawa Y, Porco J A, Wong C H. J. Am. Chem. Soc., 1991, 113:6187.
[53] Arnone A, Bravo P, Donadelli A, Resnati G. Tetrahedron, 1996, 52:131.
[54] Arnone A, Bravo P, Donadelli A, Resnati G. J. Chem. Soc., Chem. Commun., 1993, 984.
[55] Qiu X L, Qing F L. J. Org. Chem., 2005, 70:3826.
[56] Qiu X L, Qing F L. Bioorg. Med Chem., 2005, 13:277.
[57] Wang R W, Qing F L. Org. Lett., 2005, 7:2189.
[58] Wang R W, Qiu X L, Bols M, Ortega-Caballero F, Qing F L. J. Med. Chem., 2006, 49:2989.
[59] Xu X H, Qiu X L, Zhang X G, Qing F L. J. Org. Chem., 2006, 71:2820.
[60] Chen Q, Qing F L. Tetrahedron, 2007, 63:11965.
[61] Wang B L, Jiang Z X, You Z W, Qing F L. Tetrahedron, 2007, 63:12671.
[62] Xu X H, You Z W, Zhang X G, Qing F L. J. Fluorine Chem., 2007, 128:535.
[63] Yang Y Y, Xu J, You Z W, Xu X H, Qiu X L, Qing F L. Org. Lett., 2007, 9:5437.
[64] Yue X Y, Wu Y Y, Qing F L. Tetrahedron, 2007, 63:1560.
[65] Yue X Y, Qiu X L, Qing F L. J. Fluorine Chem., 2008, 129:866.
[66] Li R J, Bols M, Rousseau C, Zhang X G, Wang R W, Qing F L. Tetrahedron, 2009, 65:3717.
[67] Yang Y, Zheng F, Bols M, Marinescu L G, Qing F L. J. Fluorine Chem., 2011, 132:838.
[68] Yang Y, Zheng F, Qing F L. Tetrahedron, 2011, 67:3388.
[69] Asano N, Ikeda K, Yu L, Kato A, Takebayashi K, Adachi I, Kato I, Ouchi H, Takahata H, Fleet G W J. Tetrahedron:Asymmetry, 2005, 16:223.
[70] Blackburn C M, England D A, Kolkmann F. Chem. Commun., 1981, 930.
[71] Lillelund V H, Jensen H H, Liang X F, Bols M. Chem. Rev., 2002, 102:515.
[72] Biffinger J C, Kim H W, DiMagno S G. ChemBioChem, 2004, 5:622.
[73] Jiang X Y, Xu X H, Qing F L. Chin. Chem. Lett., 2014, 25:1115.
[74] Gautier-Lefebvre I, Behr G B, Guillerm G, Ryder N S. Bioorg. Med. Chem. Lett., 2000, 10:1483.
[75] Gautier-Lefebvre I, Behr G B, Guillerm G, Muzard M. Eur. J. Med. Chem., 2005, 40:1255.
[76] Djebaili M, Behr J B. J. Enzyme Inhib. Med. Chem., 2005, 20:123.
[77] Thaharn W, Bootwicha T, Soorukram D, Kuhakarn C, Prabpai S, Kongsaeree P, Tuchinda P, Reutrakul V, Pohmakotr M. J. Org. Chem., 2012, 77:8465.
[78] Korvorapun K, Soorukram D, Kuhakarn C, Tuchinda P, Reutrakul V, Pohmakotr M. Chem. Asian J., 2015, 10:948.
[79] Ruppert I, Schlich K, Volbach W. Tetrahedron Lett., 1984, 25:2195.
[80] Beckers H, Bürger H, Bursch P, Ruppert I. J. Organomet. Chem., 1986, 316:41.
[81] Prakash G K S, Krishnamurti R, Olah G A. J. Am. Chem. Soc., 1989, 111:393.
[82] Ma J A, Cahard D. J. Fluorine Chem., 2007, 128:975.
[83] Liu X, Xu C, Wang M, Liu Q. Chem. Rev., 2015, 115:683.
[84] Li Y X, Kinami K, Hirokami Y, Kato A, Su J K, Jia Y M, Fleet G W J, Yu C Y. Org. Biomol. Chem., 2016, 14:2249.
[85] Cruz F P d, Newberry S, Jenkinson S F, Wormald M R, Butters T D, Alonzi D S, Nakagawa S, Becq F, Norez C, Nash R J, Kato A, Fleet G W J. Tetrahedron Lett., 2011, 52:219.
[86] Forcella M, Parenti P, Cipolla L, Gregori M, Schirone R, Fusi P, Cardona F, Goti A, Parmeggiani C. Glycobiology, 2010, 20:1186.
[87] Parmeggiani C, Catarzi S, Matassini C, D'Adamio G, Morrone A, Goti A, Paoli P, Cardona F. ChemBioChem, 2015, 16:2054.
[88] Paszkowska J, Fernandez O N, Wandzik I, Boudesoque S, Dupont L, Plantier-Royon R, Behr J B. Eur. J. Org. Chem., 2015, 1198.
[89] Smart B E. J. Fluorine Chem., 2001, 109:3.
[90] Purser S, Moore P R, Swallow S, Gouverneur V. Chem. Soc. Rev., 2008, 37:320.
[91] Matkhalikova S F, Malikov V M, Yunusov S Y. Khim. Prir. Soedin., 1969, 5:30.
[92] Matkhalikova S F, Malikov V M, Yunusov S Y. Khim. Prir. Soedin., 1969, 5:606.
[93] Khanov M T, Sultanov M B, Egorova T A. Farmakol. Alkaloidov Serdech. Glikoyidov., 1971, 210.
[94] Shibano M, Tsukamoto D, Masuda A, Tanaka Y, Kusano G. Chem. Pharm. Bull., 2001, 49:1362.
[95] Tsou E L, Chen S Y, Yang M H, Wang S C, Cheng T R R, Cheng W C. Bioorg. Med. Chem., 2008, 16:10198.
[96] Liu C Y, Meng A G, Zhan H. Acta Academiae Medicinae Militaris Tertiae, 2010, 32:369.
[97] 孟爱国(Meng A G), 刘春艳(Liu C Y), 马红翠(Ma H C). 中国实验方剂学杂志(Chinese Journal of Experimental Traditional Medical Formulae), 2011, 17(16):217.
[98] Li Y X, Iwaki R, Kato A, Jia Y M, Fleet G W J, Zhao X, Xiao M, Yu C Y. Eur. J. Org. Chem., 2016, 1429.
[99] Lee C K, Sim K Y, Zhu J. Tetrahedron, 1992, 48:8541.
[100] Lee C K, Jiang H X, Koh L L, Xu Y. Carbohydr. Res., 1993, 239:309.
[101] Andersen S M, Ebner M, Ekhart C W, Gradnig G, Legler G, Lundt I, Stütz A E, Withers S G, Wrodnigg T. Carbohydr. Res., 1997, 301:155.
[102] Berger A, Dax K, Gradnig G, Grassberger V, Stütz A E, Ungerank M, Legler G, Bause E. Bioorg. Med. Chem. Lett., 1992, 2:27.
[103] Revuelta J, Cicchi S, Goti A, Brandi A. Synthesis, 2007, 485.
[104] Wang W B, Huang M H, Li Y X, Rui P X, Hu X G, Zhang W, Su J K, Zhang Z L, Zhu J S, Xu W H, Xie X Q, Jia Y M, Yu C Y. Synlett, 2010, 3:488.
[105] Zhao W B, Nakagawa S, Kato A, Adachi I, Jia Y M, Hu X G, Fleet G W J, Wilson F X, Horne G, Yoshihara A, Izumori K, Yu C Y. J. Org. Chem., 2013, 78:3208.
[106] Zhu J S, Nakagawa S, Chen W, Adachi I, Jia Y M, Hu X G, Fleet G W J, Wilson F X, Nitoda T, Horne G, van Well R, Kato A, Yu C Y. J. Org. Chem., 2013, 78:10298.
[107] Hu X G, Bartholomew B, Nash R J, Wilson F X, Fleet G W J, Nakagawa S, Kato A, Jia Y M, Well R V, Yu C Y. Org. Lett., 2010, 12:2562.
[108] Zhao H, Kato A, Sato K, Jia Y M, Yu C Y. J. Org. Chem., 2013, 78:7896.
[109] Song Y Y, Kinami K, Kato A, Jia Y M, Li Y X, Fleet G W J, Yu C Y. Org. Biomol. Chem., 2016, 14:5157.
[110] Qian B C, Kamori A, Kinami K, Kato A, Li Y X, Fleet G W J, Yu C Y. Org. Biomol. Chem., 2016, 14:4488.
[111] Liautard V, Christina A E, Desvergnes V, Martin O R. J. Org. Chem., 2006, 71:7337.
[112] Li Y X, Huang M H, Yamashita Y, Kato A, Jia Y M, Wang W B, Fleet G W J, Nash R J, Yu C Y. Org. Biomol. Chem., 2011, 9:3405.
[113] Hendry D, Hough L, Richardson A C. Tetrahedron Lett., 1987, 28:4597.
[114] Pandey G, Dumbre S G, Pal S, Khan M I, Shabab M. Tetrahedron, 2007, 63:4756.
[115] Furneaux R H, Mason J M, Tyler P C. Tetrahedron Lett., 1994, 35:3143.
[116] Vurchio C, Cordero F M, Faggi C, Macchi B, Frezza C, Grelli S, Brandi A. Tetrahedron, 2015, 71:5806.
[117] Cordero F M, Vurchio C, Faggi C, Brandi A. Org. Chem. Front., 2016, 3:1651.
[118] Wu L, Chen P H, Liu G S. Org. Lett., 2016, 18:960.
[119] Thonhofer M, Gonzalez Santana A, Fischer R, Torvisco Gomez A, Saf R, Schalli M, Stütz A E, Withers S G. Carbohydr. Res., 2016, 420:6.
[120] Fan J Q, Ishii S, Asano N, Suzuki Y. Nat. Med., 1999, 5:112.
[121] Li Y X, Shimada Y, Adachi I, Kato A, Jia Y M, Fleet G W J, Xiao M, Yu C Y. J. Org. Chem., 2015, 80:5151.
[122] Li Y X, Shimada Y, Sato K, Kato A, Zhang W, Jia Y M, Fleet G W J, Xiao M, Yu C Y. Org. Lett., 2015, 17:716.
[123] Huang M H, Li Y X, Jia Y M, Yu C Y. Molecules, 2013, 18:6723.
[124] Win-Mason A L, Jongkees S A K, Withers S G, Tyler P C, Timmer M S M, Stocker B L. J. Org. Chem., 2011, 76:9611.
[125] Wang J T, Lin T C, Chen Y H, Lin C H, Fang J M. MedChemComm, 2013, 4:783.
[126] Stocker B L, Jongkees S A K, Win-Mason A L, Dangerfield E M, Withers S G, Timmer M S M. Carbohydr. Res., 2013, 367:29.
[127] Martínez R F, Araújo N, Jenkinson S F, Nakagawa S, Kato A, Fleet G W J. Bioorg. Med. Chem., 2013, 21:4813.
[128] Wu X, Zhang F Y, Zhu J, Song C, Xiong D C, Zhou Y, Cui Y, Ye X S. Chem. Asian J., 2014, 9:2260.
[129] Mattes H, Benezra C. Tetrahedron Lett., 1985, 26:5697.
[130] Petrier C, Luche J L. J. Org. Chem., 1985, 50:910.
[131] Nishimura Y, Kudo T, Kondo S, Takeuchi T. J. Antibiot., 1992, 45:963.
[132] Nishimura Y. Curr. Top. Med. Chem., 2003, 3:575.
[133] Banks R E, Smart B E, Tatlow J C, Organofluorine Chemistry, Principles and Commercial Applications, 1st ed. Plenum:New York, 1994.
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