Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (11): 2202-2216.DOI: 10.6023/cjoc201405010 Previous Articles Next Articles
刘亚君, 郭翔海, 白鹏
收稿日期:
2014-05-07
修回日期:
2014-06-10
发布日期:
2014-07-03
通讯作者:
郭翔海,guoxh@tju.edu.cn
E-mail:guoxh@tju.edu.cn
基金资助:
国家自然科学基金(No.21202116)资助项目.
Liu Yajun, Guo Xianghai, Bai Peng
Received:
2014-05-07
Revised:
2014-06-10
Published:
2014-07-03
Supported by:
Project supported by the National Natural Science Foundation of China (No.21202116).
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Liu Yajun, Guo Xianghai, Bai Peng. Recent Progress in the Syntheses of Carbocyclic Nucleosides[J]. Chin. J. Org. Chem., 2014, 34(11): 2202-2216.
[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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