Synthesis and structural elucidation of 1-(3-C-ethynyl-4-thio-ß-D-ribofuranosyl)cytosine (4’-thioECyd)

Journal of the Chemical Society. Perkin Transactions 1

Volumn 2, Issue 19, 2002, Pages 2182-2189

  Minakawa, Noriaki ^a   Kaga, Daisuke ^a   Kato, Yuka ^a   Endo, Kanji ^b   Tanaka, Motohiro ^c   Sasaki, Takuma ^c   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b TAIHO PHARMACEUTICAL CO LTD   (Japan)

^c KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CHEMICAL REACTIONS; CONFORMATIONS; CRYSTAL STRUCTURE; DERIVATIVES; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

BENZOYLCYTOSINE; CERIUM TRIMETHYLSILYLACETYLIDE; GLYCOSYL BOND; PUMMERER REACTION; RIBOSE; STRUCTURAL ELUCIDATION; THIOCYTIDINE DERIVATIVE; THIONUCLEOSIDES;

ORGANIC COMPOUNDS;

EID: 0036026278     PISSN: 14727781     EISSN: 13645463     Source Type: Journal    
DOI: 10.1039/b204993g     Document Type: Article

References (27)

1. M. Yokoyama Synthesis 2000, 12, 1637-1655.
2. M.R. Dyson, P.L. Coe, R.T. Walker J. Med. Chem. 1991, 34, 2782-2786.
3. K.N. Tiwari, A.T. Sfortnacy-Fowler, L. Cappellacci, W.B. Parker, W.R. Waud, J.A. Montgomery, J.A. Secrist III Nucleosides Nucleotides Nucleic Acids 2000, 19, 329-340.
4. Y. Yoshimura, K. Kitano, H. Satoh, M. Watanabe, S. Miura, S. Sakata, T. Sasaki, A. Matsuda J. Org. Chem. 1996, 61, 822-823.
5. A. Matsuda, K. Takenuki, M. Tanaka, T. Sasaki, T. Ueda J. Med. Chem. 1991, 34, 812-819.
6. K. Yamagami, A. Fujii, M. Arita, T Okumoto, S. Sakata, A. Matsuda, T. Ueda, T. Sasaki Cancer Res. 1991, 51, 2319-2323.
7. T. Ono, A. Fujii, M. Hosoya, T. Okumoto, S. Sakata, A. Matsuda, T. Sasaki Biochem. Pharmacol. 1996, 52, 1279-1285.
8. H. Hattori, M. Tanaka, M. Fukushima, T. Sasaki, A. Matsuda J. Med. Chem. 1996, 39, 5005-5011.
9. S. Tabata, M. Tanaka, Y. Endo, T. Obata, A. Matsuda, T. Sasaki Cancer Lett. 1997, 116, 225-231.
10. S. Takatori, H. Kanda, K. Takenaka, Y. Wataya, A. Matsuda, M. Fukushima, Y. Shimamoto, M. Tanaka, T. Sasaki Cancer Chemother. Pharmacol. 1999, 44, 97-104.
11. Y. Shimamoto, H. Kazuno, Y. Murakami, A. Azuma, K. Koizumi, A. Matsuda, T. Sasaki, M. Fukushima Jpn. J. Cancer Res. 2002, 93, 445-452.
12. T. Naka, N. Nishizono, N. Minakawa, A. Matsuda Tetrahedron Lett. 1999, 40, 6297-6300.
13. T. Naka, N. Minakawa, H. Abe, D. Kaga, A. Matsuda J. Am. Chem. Soc. 2000, 122, 7233-7243.
14. K. Nagasawa, A. Yoneta Chem. Pharm. Bull. 1985, 33, 5048-5052.
15. A.K. Bose, B. Lal Tetrahedron Lett. 1973, 3937-3940.
16. O. Yamazaki, H. Togo, M. Yokoyama J. Chem. Soc., Perkin Trans. 1 1999, 2891-2896.
17. P.M.J. Jung, A. Burger, J.-F. Biellmann Tetrahedron Lett. 1995, 36, 1031-1034.
18. P.M.J. Jung, A. Burger, J.-F. Biellmann J. Org. Chem. 1997, 62, 8309-8314.
19. H. Hattori, E. Nozawa, T. Iino, Y. Yoshimura, S. Shuto, Y. Shimamoto, M. Nomura, M. Fukushima, M. Tanaka, T. Sasaki, A. Matsuda J. Med. Chem. 1998, 41, 2892-2902.
20. G.H. Hakimelahi, Z.A. Proba, K.K. Ogilvie Tetrahedron Lett. 1981, 22, 4775-4778.
21. M. Bobek, A. Bloch, R. Parthasarathy, R.L. Whistler J. Med. Chem. 1975, 18, 784-787.
22. L.H. Koole, J. Plavec, H. Liu, B.R. Vincent, M.R. Dyson, P.L. Coe, R.T. Walker, G.W. Hardy, S.G. Rahim, J. Chattopadhyaya J. Am. Chem. Soc. 1992, 114, 9936-9943.
23. J. Uenishi, K. Takahashi, M. Motoyama, H. Akashi Chem. Lett. 1993, 255-256.
24. J.A. Secrist III, K.N. Tiwari, A.T. Sfortnacy-Fowler, L. Messini, J.M. Riordan, J.A. Montgomery J. Med. Chem. 1998, 41, 3865-3871.
25. C. Altona, M. Sundaralingam J. Am. Chem. Soc. 1973, 95, 2333-2344.
26. D.B. Davies, S.S. Danyluk Biochemistry 1974, 13, 4417-4434.
27. C. Leydier, L. Bellon, J.-L. Barascut, J. Deydier, G. Maury, H. Pelicano, M.A.E. Alaoui, J.-L. Imbach Nucleosides Nucleotides 1994, 13, 2035-2050.