3'-叠氮D/L-核苷的合成
收稿日期: 2017-08-02
修回日期: 2017-10-24
网络出版日期: 2017-10-31
基金资助
国务院重点华侨华人创业团队经费资助项目.
Synthesis of 3'-Azido-D/L-nucleosides
Received date: 2017-08-02
Revised date: 2017-10-24
Online published: 2017-10-31
Supported by
Project supported by the Key Overseas Chinese Entrepreneurial Team Grant, Awarded by Overseas Chinese Affairs Office of the State Council.
任行 , 陶京朝 , 安浩云 . 3'-叠氮D/L-核苷的合成[J]. 有机化学, 2018 , 38(1) : 138 -147 . DOI: 10.6023/cjoc201708005
Two orthorganally protected 3'-azido-3'-deoxy-D/L-ribosides were synthesized and successfully glycosylated with various pyrimidine, pyridine and purine related heterocyclic bases. 3'-Azido-3'-deoxy-D-pyrimidine nucleosides, purine nucleosides as well as 3'-azido-3'-deoxy-L-nucleosides were synthesized. 3'-Azido-3'-deoxy-6-azauridine, 4-deoxyuridine, 2-thiouridine, 3-deazauridine, nitropyridinone and isocytidine derivatives were also synthesized as the drug analogues to explore their biological properties. 14 final products are novel and well characterized, while all of the 31 final products were synthesized by the new strategy from the corresponding novel key intermediates. The two key intermediates can be utilized to make all kinds of novel nucleoside derivatives by glycosylating with various heterocyclic bases.
Key words： azido-nucleoside; L-nucleoside; D-nucleoside; synthesis; glycosylation
[1] (a) Silvestris, N.; Daprile, M.; Andreola, G.; Locopo, N.; Marini, L.; Cructitta, E.; Delena, M.; Lorusso, V. Int. J. Oncol. 2004, 24, 389.
(b) Riggs, A. D.; Jones, P. A. Adv. Cancer Res. 1983, 40, 1.
(c) Momparler, R. L.; Momparler, L. F. Cancer Chemother. Pharmacol. 1989, 25, 51.
(d) Asselah, T. Expert Opin. Pharmacother. 2014, 15, 121.
[2] (a) Mitsuya, H.; Weinhold, K. J.; Furman, P. A.; St Clair, M. H.; Lehrman, S. N.; Gallo, R. C.; Bolognesi, D.; Barry, D. W.; Broder, S. Proc. Natl. Acad. Sci. U. S. A. 1985, 82, 7096.
(b) De Clercq, E. Biochem. Pharmacol. 1994, 47, 155.
[3] (a) Wang, Q.; Hu, W.-D.; Wang, S.-Y.; Pan, Z.-L.; Tao, L.; Guo, X.-H.; Qian, K-D.; Chen, C.-H.; Lee, K-H.; Chang, J.-B. Eur. J. Med. Chem. 2011, 46, 4178.
(b) Zheng, L.-Y.; Wang, Q.; Yang, X.-R.; Guo, X.-H.; Chen, L.; Tao, L.; Dong, L.-H.; Li, Y.-J.; An, H.; Yu, X.-J.; Wang, Q.-D.; Chang, J.-B. Antiviral Ther. 2012, 17, 679.
[4] (a) Klinchan, C.; Hsu, Y.-L.; Lo, L-C.; Pluempanupat, W.; Chuawong, P. Tetrahedron Lett. 2014, 55, 6207.
(b) Schirmeister-Tichya, H.; Iaconoc, K. T.; Mutoc, N. F.; Homanb, J. W.; Suhadolnikb, R. J.; Pfleiderer, W. Helv. Chim Acta 1999, 82, 597.
(c) Zhang, L.; Cui, Z.-Y.; Zhang, B.-L. Helv. Chim. Acta 2003, 86, 703.
(d) Robins, M. J.; Hawrelak, S. D.; Hernández, A. E.; Wnuk, S. F. Nucleosides, Nucleotides Nucleic Acids 1992, 11, 821.
[5] (a) Zatsepin, T. S.; Stetsenko, D. A.; Gait, M. J.; Oretskaya, T. S. Bioconjugate Chem. 2005, 16, 471.
(b) Matulic-Adamic, J.; Serebryany, V.; Haeberli, P.; Mokler, V. R.; Beigelman, L. Bioconjugate Chem. 2002, 13, 1071.
[6] (a) Roy, V.; Zerrouki, R.; Krausz, P.; Laumond, G.; Aubertin, A. M. Nucleosides, Nucleotides Nucleic Acids 2007, 26, 413.
(b) Soenens, J.; François, G. F.; Eeckhout, E. V.; Herdewijn, P. Nucleosides, Nucleotides Nucleic Acids 1995, 14, 409.
(c) Ozols, A. M.; Azhayev, A. V.; Dyatkina, N. B.; Krayevsky, A. A. Synthesis 1980, 557.
(d) Liang, C. W.; Kim, M. J.; Jeong, L. S.; Chun, M. W. Nucleosides, Nucleotides Nucleic Acids 2003, 22, 2039;
[7] Arya, A.; Mathur, D.; Tyagi, A.; Kumar, R.; Kumar, V.; Olsen, C. E.; Saxena, R. K.; Prasad, A. K. Nucleosides, Nucleotides Nucleic Acids 2013, 32, 646.
[8] (a) Lin, T.-S.; Yang, J.-H.; Liu, M.-C.; Shen, Z.-Y.; Cheng, Y.-C.; Prusoff, W. H.; Birnbaum, G. I.; Giziewicz, J.; Ghazzouli, I.; Brankovan, V.; Feng, J.-S.; Hsiun, G.-D. J. Med. Chem. 1991, 34, 693.
(b) Greco, N. J.; Tor, Y. Tetrahedron 2007, 63, 3515.
[9] (a) Handschumacher, R. E. J. Bid. Chem. 1960, 235, 764.
(b) Capek, A.; Svatek, E.; Tadra, M. Folia Microbiol. 1963, 8, 304.
(c) Skoda, J. Prog. Nucleic Acid Res. Mol. Biol. 1963, 2, 197.
[10] (a) Robins, M. L.; Currie, B. L.; Robins, R. K.; Bloch, A. Proc. Am. Assoc. Cancer Res. 1969, 10, 73.
(b) McPartland, R. P.; Wang, M. C.; Bloch, A.; Weinfeld, H. Cancer Res. 1974, 34, 3107.
(c) Khare, G. P.; Sidwell, R. W.; Huffman, J. H.; Tolman, R. L.; Robins, R. K. Proc. Soc. Exp. Biol. Med. 1972, 140, 880.
(d) Shannon, W. M.; Brockman, R. W.; Westbrook, L.; Shaddix, S.; Schabel, F. M. Jr. J. Natl. Cancer Inst. 1974, 52, 199.
[11] (a) Zhou, L.; Cheng, X.; Connolly, B. A.; Dickman, M. J.; Hurd, P. J.; Hornby, D. P. J. Mol. Biol. 2002, 321, 591.
(b) Driscoll, J. S.; Marquez V. E.; Plowman, J.; Liu, P. S.; Kelley, J. A.; Barchi, J. J. Jr. J. Med. Chem. 1991, 34, 3280.
[12] Robins, M. J.; Miles, R. W.; Samano, M. C.; Kaspar, R. L. J. Org. Chem. 2001, 66, 8204.
[13] Kim, B.-T.; Kim, S.-K.; Lee, S.-J.; Hwang, K.-J. Bull. Korea Chem. Soc. 2004, 25, 243;
[14] (a) Chong, Y.; Gumina, G.; Mathew, J. S.; Schinazi, R. F.; Chu, C. K. J. Med. Chem. 2003, 46, 3245.
(b) Ma, T.-W.; Pai, S. B.; Zhu, Y. L.; Lin, J. S.; Shanmuganathan, K.; Du, J.-F.; Wang, C.-G.; Kim, H.-B.; Newton, M. G.; Cheng, Y. C.; Chu, D. K. J. Med. Chem. 1996, 39, 2835.
(c) Kotra, L. P.; Xiang, Y.-J.; Newton, M. G.; Schinazi, R. F.; Cheng, Y.-C.; Chu, C. K. J. Med. Chem. 1997, 40, 3635.
[15] Cooperwood, J. S.; Boyd, V.; Gumina, G.; Chu, C. K. Nucleosides, Nucleotides Nucleic Acids 2000, 19, 219.
[16] (a) Hassan, A. E. A.; Abou-Elkair, R. A. I.; Montgomery, J. A.; Secrist Ⅲ, J. A. Nucleosides, Nucleotides Nucleic Acids 2000, 19, 1123.
(b) Marasco, C. J. Jr.; Pera, P. J.; Spiess, A. J.; Bernacki, R.; Sufrin, J. R. Molecules 2005, 10, 1015.
[17] Rompaey, P. V.; Nauwelaerts, K.; Vanheusden, V.; Rozenski, J.; Munier-Lehmann, H.; Herdewijn, P.; Calenbergh, S. V. Eur. J. Org. Chem. 2003, 2911.
[18] Ora, M.; Mattila, K.; Lonnberg, T.; Oivanen, M.; Lonnberg, H. J. Am. Chem. Soc. 2002, 124, 14364.
[19] Urata, Y.; Mitsu, Y.; Nakamura, K. T. Chem. Pharm. Bull 1981, 29, 2769.
[20] Gadthula, S.; Chu, C. K.; Schinazi, R. F. Nucleosides, Nucleotides, Nucleic Acids 2005, 24, 1707.
[21] Botta, O.; Moyroud, E.; Lobato, C.; Strazewski, P. Tetrahedron 1998, 54, 13529.
[22] Gao, Z.-G.; Duong, H. T.; Sonina, T.; Kim, S.-K.; Rompaey, P. V.; Calenbergh, S. V.; Mamedova, L.; Kim, H. O.; Kim, M. J.; Kim, A. Y.; Liang, B. R.; Jeong, L. S.; Jacobson, K. A. J. Med. Chem. 2006, 49, 2689.
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