近年碳环核苷类似物的合成研究进展
收稿日期: 2014-05-07
修回日期: 2014-06-10
网络出版日期: 2014-07-03
基金资助
国家自然科学基金(No.21202116)资助项目.
Recent Progress in the Syntheses of Carbocyclic Nucleosides
Received date: 2014-05-07
Revised date: 2014-06-10
Online published: 2014-07-03
Supported by
Project supported by the National Natural Science Foundation of China (No.21202116).
刘亚君 , 郭翔海 , 白鹏 . 近年碳环核苷类似物的合成研究进展[J]. 有机化学, 2014 , 34(11) : 2202 -2216 . DOI: 10.6023/cjoc201405010
Carbocyclic nucleosides are nucleoside analogues whose furanose rings are substituted by carbocycles. As analogues, many carbocyclic nucleosides show good antiviral or antitumor activities. Also, due to the absence of a typical glycosidic bond, carbocyclic nucleosides usually exhibit more metabolic stabilities to phosphorylases and hydrolases than natural nucleosides. Therefore, medicinal chemists have focused their attention on designing and preparing new carbocyclic nucleoside analogues, in efforts to discover new more powerful and safe antiviral agents. The syntheses of carbocyclic nucleosides in the past five years classified by different types of bases are reviewed in this article, denoted as purine carbocyclic nucleosides, pyrimidine carbocyclic nucleosides and carbocyclic analogues of C-nucleosides, with an emphasis on the synthesis of purine carbocyclic nucleosides. In the end, the problems and future trends of carbocyclic nucleoside research are discussed. It is still a challenge to intelligently design and efficiently synthesize the novel carbocyclic nucleosides targeted for some special purposes.
Key words： carbocyclic nucleosides; antiviral activity; synthesis
[1] Jeong, L. S.; Lee, J. A. Antiviral Chem. Chemother. 2004, 15, 235.
[2] Matyugina, E. S.; Khandazhinskaya, A. L.; Kochetkov, S. N. Russ. Chem. Rev. 2012, 81, 729.
[3] Montgomery, J. A. Med. Res. Rev. 1982, 2, 271.
[4] (a) Daluge, S. M.; Good, S. S.; Faletto, M. B. Antimicrob. Agents Chemother. 1997, 41, 1082. (b) Innaimo, S. F.; Seifer, M.; Bisacchi, G. S.; Standring, D. N.; Zahler, R.; Colonno, R. J. Antimicrob. Agents Chemother. 1997, 41, 1444.
[5] Guo, X.-H.; Kang, H.; Zheng, L.-X.; Jiang, S.-D. Chin. J. Org. Chem. 2011, 31, 176 (in Chinese).(郭翔海, 康宏, 郑岚曦, 姜申德, 有机化学, 2011, 31, 176.)
[6] Boutureira, O.; Isabel, M. M.; Díaz, Y.; Castillón, S. Chem. Soc. Rev. 2013, 42, 5056.
[7] (a) Crimmins, M. T. Tetrahedron 1998, 54, 9229. (b) Zhu, X.-F. Nucleosides Nucleotides 2000, 19, 651. (c) Douadi, A.; Brémond, P.; Lanez, T.; Pannecouque, C.; Audran, G. Synlett 2011, 111.
[8] Fan, X.-S.; Zhang, X.-Y.; Wang, X.; Qu, G.-R. Chin. J. Org. Chem. 2008, 28, 1888 (in Chinese).(范学森, 张新迎, 王霞, 渠桂荣, 有机化学, 2008, 28, 1888.)
[9] Kusuka, T.; Yamamoto, H.; Shibata, M.; Muroi, M.; Kishi, T.; Mizuno, K. J. Antibiot. 1968, 21, 255.
[10] Yaginuma, S.; Muto, N.; Tsujino, M.; Sudate, Y.; Hayashi, M.; Otani, M. J. Antibiot. 1981, 34, 359.
[11] (a) Vince, R.; Hua, M.; Brownell, J.; Daluge, S.; Lee, F.; Shannon, W. M.; Lavelle, G. C.; Qualls, J.; Weislow, O. S.; Kiser, R.; Canonico, P. G.; Schultz, R. H.; Narayanan, V. L.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Biochem. Biophys. Res. Commun. 1988, 156, 1046. (b) Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17.
[12] (a) Hayashi, M.; Yaginuma, S.; Muto, N.; Tsujino, M. Nucleic Acids Res. 1980, 8, 65. (b) Comin, M. J.; Leitofuter, J.; Rodriguez, J. B. Tetrahedron 2002, 58, 3129.
[13] (a) Bodenteich, M.; Marquez, V. E.; Hallows, W. H.; Goldstein, B. M. J. Org. Chem. 1992, 57, 2071. (b) Zhang, H.; Schinazi, R. F.; Chu, C. K. Bioorg. Med. Chem. 2006, 14, 8314.
[14] Kim, Y. A.; Rawal, R. K.; Yoo, J.; Sharon, A.; Jha, A. K.; Chu, C. K.; Rais, R. H.; Al Safarjalani, O. N.; Naguib, F. N.; El Kouni, M. H. Bioorg. Med. Chem. 2010, 18, 3403.
[15] Jin, Y. H.; Liu, P.; Wang, J.; Baker, R.; Huggins, J.; Chu, C. K. J. Org. Chem. 2003, 68, 9012.
[16] Wang, P.; Agrofoglio, L.; Newton, M.; Chu, C. K. J. Org. Chem. 1999, 64, 4173.
[17] Shuto, S.; Obara, T.; Saito, Y.; Andrei, G.; Snoeck, R.; De, C. E.; Matsuda, A. J. Med. Chem. 1996, 39, 2392.
[18] Ye, W.; He, M.; Schneller, S. W. Tetrahedron Lett. 2009, 50, 7156.
[19] Palmer, A. M.; Jäger, V. Eur. J. Org. Chem. 2001, 7, 1293.
[20] Chattopadhyay, A.; Tripathy, S. J. Org. Chem. 2011, 76, 5856.
[21] Boyle, G. A.; Edlin, C. D.; Li, Y.; Liotta, D. C.; Morgans, G. L.; Musonda, C. C. Org. Biomol. Chem. 2012, 10, 1870.
[22] Forró, E.; Fülöp, F. Tetrahedron: Asymmetry 2004, 15, 2875.
[23] Liu, C.; Qi, C.; Schneller, S. W. Tetrahedron Lett. 2011, 52, 4931.
[24] Vanden, B. M.; Hylkema, M. N.; Versluis, M.; Postma, D. S. Drugs R&D 2007, 8, 13.
[25] Diniz, C.; Borges, F.; Santana, L.; Uriarte, E.; Oliveira, J. M. A.; Gonçalves, J.; Fresco, P. Curr. Pharm. Des. 2008, 14, 1968.
[26] Beattie, D.; Brearley, A.; Brown, Z.; Charlton, S. J.; Cox, B.; Fairhurst, R. A.; Fozard, J. R.; Gedeck, P.; Kirkham, P.; Meja, K.; Nanson, L.; Neef, J.; Oakman, H.; Spooner, G.; Taylor, R. J.; Turner, R. J.; West, R.; Woodward, H. Bioorg. Med. Chem. Lett. 2010, 20, 1219.
[27] (a) Wang, J.; Jin, Y.; Rapp, K. L.; Bennett, M.; Schinazi, R. F.; Chu, C. K. J. Med. Chem. 2005, 48, 3736. (b) Chu, C. K.; Ma, T.; Shanmuganathan, K.; Wang, C.; Xiang, Y.; Pai, S. B.; Yao, G. Q.; Sommadossi, J. P.; Cheng, Y. C. Antimicrob. Agents Chemother. 1995, 39, 979.
[28] Montgomery, J. A.; Shortnacy-Fowler, A. T.; Clayton, S. D.; Riordan, J. M.; Secrist, J. A. J. Med. Chem. 1992, 35, 397.
[29] Wang, J.; Singh, U. S.; Rawal, R. K.; Sugiyama, M.; Yoo, J.; Jha, A. K.; Scroggin, M.; Huang, Z.; Murray, M. G.; Govindarajan, R.; Tanaka, Y.; Korba, B.; Chu, C. K. Bioorg. Med. Chem. Lett. 2011, 21, 6328.
[30] Gadthula, S.; Rawal, R. K.; Sharon, A.; Wu, D.; Korba, B.; Chu, C. K. Bioorg. Med. Chem. Lett. 2011, 21, 3982.
[31] Singh, U. S.; Mishra, R. C.; Shankar, R.; Chu, C. K. J. Org. Chem. 2014, 79, 3917.
[32] Moon, H. R.; Choi, W. J.; Kim, H. O.; Jeong, L. S. Tetrahedron: Asymmetry 2002, 13, 1189.
[33] eong, L. S.; Lee, J. A. Antiviral Chem. Chemother. 2004, 15, 235.
[34] Marquez, V. E.; Hughes, S. H.; Sei, S.; Agbaria, R. Antiviral Res. 2006, 71, 268.
[35] Katagiri, N.; Yamatoya, Y.; Ishikura, M. Tetrahedron Lett. 1999, 40, 9069.
[36] Ji, C.; Miller, M. J. Tetrahedron Lett. 2010, 51, 3789.
[37] Moggio, Y.; Legnani, L.; Bovio, B.; Memeo, M. G.; Quadrelli, P. Tetrahedron 2012, 68, 1384.
[38] Quadrelli, P.; Mella, M.; Legnani, L.; Al-Saad, D. Eur. J. Org. Chem. 2013, 21, 4655.
[39] Tanase, C. I.; Draghici, C.; Caproiu, M. T.; Shova, S.; Mathe, C.; Cocu, F. G.; Enache, C.; Maganu, M. Bioorg. Med. Chem. 2014, 22, 513.
[40] (a) Gordon, R. K.; Ginalski, K.; Rudnicki, W. R.; Rychlewski, L.; Pankaskie, M. C.; Bujnicki, J. M.; Chiang, P. K. Eur. J. Biochem. 2003, 270, 3507. (b) Maki, A. S.; Kim, T. W.; Kool, E. T. Biochemistry 2004, 43, 1102. (c) Bennet, L. J.; Brocman, R. W.; Allan, P. W.; Rose, L. M.; Shaddix, S. C. Biochem. Pharmacol. Rev. 1988, 7, 1233.
[41] Montgomery, J. A.; Clayton, S. J.; Thomas, H. J.; Shannon, W. M.; Arnett, G.; Bodner, A. J.; King, I.-K.; Cantoni, G. L.; Chiang, P. K. J. Med. Chem. 1982, 25, 626.
[42] (a) Tseng, C. K. H.; Marquez, V. E.; Fuller, R. W.; Goldstein, B. M.; Haines, D. R.; McPherson, H.; Parsons, J. L.; Shannon, W. M.; Arnett, G.; Hollingshead, M.; Driscoll, J. S. J. J. Med. Chem. 1989, 32, 1442.(b) Glazer, R. I.; Hartman, K. D.; Knode, M. C.; Richard, M. M.; Chiang, P. K.; Tseng, C. K. H.; Marquez, V. E. Biochem. Biophys. Res. Commun. 1986, 135, 688.
[43] Jha, A. K.; Sharon, A.; Rondla, R.; Chu, C. K. Tetrahedron 2009, 65, 9362.
[44] Eldrup, A. B.; Prhavc, M.; Brooks, J.; Bhat, B.; Prakash, T. P.; Song, Q.; Bera, S.; Bhat, N.; Dande, P.; Cook, P. D. J. Med. Chem. 2004, 47, 5284.
[45] Thiyagarajan, A.; Salim, M. T.; Balaraju, T.; Bal, C.; Baba, M.; Sharon, A. Bioorg. Med. Chem. Lett. 2012, 22, 7742.
[46] Cho, J. H.; Bernard, D. L.; Sidwell, R. W.; Kern, E. R.; Chu, C. K. J. Med. Chem. 2006, 49, 1140.
[47] Ugliarolo, E. A.; Gagey, D.; Lantano, B.; Moltrasio, G. Y.; Campos, R. H.; Cavallaro, L. V.; Moglioni, A. G. Bioorg. Med. Chem. 2012, 20, 5986.
[48] Matyugina, E.; Khandazhinskaya, A.; Chernousova, L.; Andreevskaya, S.; Smirnova, T.; Chizhov, A.; Karpenko, I.; Kochetkov, S.; Alexandrova, L. Bioorg. Med. Chem. 2012, 20, 6680.
[49] Trost, B. M.; Kuo, G. H.; Benneche, T. J. Am. Chem. Soc. 1988, 110, 621.
[50] Cesario, C.; Miller, M. J. J. Org. Chem. 2009, 74, 5730.
[51] Liu, L.-J.; Kim, S. W.; Lee, W. J.; Hong, J. H. Bull. Korean Chem. Soc. 2009, 30, 2989.
[52] Jonckers, T. H.; Lin, T. I.; Buyck, C.; Lachau-Durand, S.; Vandyck, K.; Van Hoof, S.; Vandekerckhove, L. A.; Hu, L.; Berke, J. M.; Vijgen, L.; Dillen, L. L.; Cummings, M. D.; de Kock, H.; Nilsson, M.; Sund, C.; Rydegard, C.; Samuelsson, B.; Rosenquist, A.; Fanning, G.; Van Emelen, K.; Simmen, K.; Raboisson, P. J. Med. Chem. 2010, 53, 8150.
[53] Li, H.; Yoo, J. C.; Hong, J. H. Bull. Korean Chem. Soc. 2011, 32, 1146.
[54] Choi, T. H.; Ahn, S. H.; Kwon, H. C.; Choi, C. W.; Awh, O. D.; Lim, S. M. Appl. Radiat. Isot. 2004, 60, 15.
[55] Alauddin, M. M.; Shahinian, A.; Park, R.; Tohme, M.; Fissekis, J. D.; Conti, P. S. J. Nucl. Med. 2004, 45, 2063.
[56] Ahn, H.; Choi, T. H.; Castro, K. D. A.; Lee, K. C.; Kim, B.; Moon, B. S.; Hong, S. H.; Lee, J. C.; Chun, K. S.; Cheon, G. J.; Lim, S. M.; An, G.; Rhee, H. J. Med. Chem. 2007, 50, 6032.
[57] Ahn, H. S.; An, G. I.; Rhee, H. J. Bull. Korean Chem. Soc. 2011, 32, 1931.
[58] (a) An, G.; Rhee, H. Nucleosides, Nucleotides Nucleic Acids 2003, 22, 437.(b) Ahn, H.; Choi, T. H.; Castro, K. D. A.; Lee, K. C.; Kim, B.; Moon, B. S.; Hong, S. H.; Lee, J. C.; Chun, K. S.; Cheon, G. J.; Lim, S. M.; An, G.; Rhee, H. J. Med. Chem. 2007, 50, 6032.
[59] Kato, A.; Yasuda, Y.; Kitamura, Y.; Kandeel, M.; Kitade, Y. Parasitol. Int. 2012, 61, 501.
[60] (a) MacKeith, R. A.; McCague, R.; Olivo, H. F.; Roberts, S. M.; Taylor, S. J.; Xiong, H. Bioorg. Med. Chem. Lett. 1994, 2, 387. (b) An, G. I.; Rhee, H. J. Nucleosides, Nucleotides Nucleic Acids 2002, 21, 65.
[61] Noguchi, Y.; Yasuda, Y.; Tashiro, M.; Kataoka, T.; Kitamura, Y.; Kandeel, M.; Kitade, Y. Parasitol. Int. 2013, 62, 368.
[62] (a) Agrofoglio, L. Curr. Org. Chem. 2006, 10, 333. (b) Shahan, M. A. E.; Nasr, A. Z. Adv. Heterocycl. Chem. 1997, 68, 223. (c) Shaban, M. A. E. Adv. Heterocycl. Chem. 1998, 70, 163.
[63] (a) Fissekis, J. D.; Markert-Creegan, B. J. Org. Chem. 1967, 32, 3595. (b) Fissekis, J. D.; Markert-Creegan, B. J. Org. Chem. 1966, 31, 2945.
[64] Rao, J. R.; Schinazi, R. F.; Chu, C. K. Bioorg. Med. Chem. 2007, 15, 839.
[65] (a) Jin, Y. L.; Hong, J. H. Bull. Korean Chem. Soc. 2005, 26, 1366.(b) Oh, C. H.; Liu, L. J.; Hong, J. H. Nucleosides, Nucleotides Nucleic Acids 2008, 27, 1144.
[66] H?ebabecký, H.; Nencka, R.; Šála, M.; Dejmek, M.; Dra?ínský, M.; Holý, A. Synthesis 2010, 23, 4119.
[67] Shealy, Y. F.; Clayton, J. D. J. Am. Chem. Soc. 1966, 88, 3885.
[68] Guo, X.-H.; Liu, C; Zheng, L.-X; Jiang, S.-D.; Shen, J.-X. Synlett 2010, 1959.
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