Citation: Ren Hang, Tao Jingchao, An Haoyun. Synthesis of 3'-Azido-D/L-nucleosides[J]. Chinese Journal of Organic Chemistry, ;2018, 38(1): 138-147. doi: 10.6023/cjoc201708005 shu

Synthesis of 3'-Azido-D/L-nucleosides

Ren Hang ^a,b ,
Tao Jingchao ^a,, ,
An Haoyun ^b

a.
College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001
b.
Zhengzhou Granlen PharmaTech, Ltd., Zhengzhou 450016

Corresponding author: Tao Jingchao, han@granlen.com
Received Date: 2 August 2017
Revised Date: 24 October 2017
Available Online: 31 January 2017
Fund Project: Project supported by the Key Overseas Chinese Entrepreneurial Team Grant, Awarded by Overseas Chinese Affairs Office of the State Council

Figures(5)

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.
- azido-nucleoside,
- L-nucleoside,
- D-nucleoside,
- synthesis,
- glycosylation
1. [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. [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. [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. [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. [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. [6]
  (a) Roy, V. ; Zerrouki, R. ; Krausz, P. ; Laumond, G. ; Aubertin, A. M. Nucleosides, Nucleotides Nucleic Acids 2007, 26, 413.
  (b) Soenens, J. ; Fran ois, 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. [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. doi: 10.1080/15257770.2013.847957
8. [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. [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. [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. [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. [12]
  Robins, M. J.; Miles, R. W.; Samano, M. C.; Kaspar, R. L. J. Org. Chem. 2001, 66, 8204. doi: 10.1021/jo010935d
13. [13]
  Kim, B.-T.; Kim, S.-K.; Lee, S.-J.; Hwang, K.-J. Bull. Korea Chem. Soc. 2004, 25, 243; doi: 10.5012/bkcs.2004.25.2.243
14. [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. [15]
  Cooperwood, J. S.; Boyd, V.; Gumina, G.; Chu, C. K. Nucleosides, Nucleotides Nucleic Acids 2000, 19, 219. doi: 10.1080/15257770008033005
16. [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. [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. [18]
  Ora, M.; Mattila, K.; Lonnberg, T.; Oivanen, M.; Lonnberg, H. J. Am. Chem. Soc. 2002, 124, 14364. doi: 10.1021/ja027499c
19. [19]
  Urata, Y.; Mitsu, Y.; Nakamura, K. T. Chem. Pharm. Bull 1981, 29, 2769. doi: 10.1248/cpb.29.2769
20. [20]
  Gadthula, S.; Chu, C. K.; Schinazi, R. F. Nucleosides, Nucleotides, Nucleic Acids 2005, 24, 1707. doi: 10.1080/15257770500267170
21. [21]
  Botta, O.; Moyroud, E.; Lobato, C.; Strazewski, P. Tetrahedron 1998, 54, 13529. doi: 10.1016/S0040-4020(98)00819-9
22. [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. doi: 10.1021/jm050968b
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