Synthesis of 4-guanidino-7-modified-Neu5Ac2en derivatives and their biological activities as influenza sialidase inhibitors

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 67, Issue 11, 2009, Pages 1105-1114

  Honda, Takeshi ^a   Masuda, Takeshi ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL CONDENSATION; ALKYL ETHERS; ANTIVIRAL ACTIVITIES; BIOLOGICAL ACTIVITIES; DIRECT ALKYLATION; HYDROPHOBIC GROUPS; IN-CELL; IN-VIVO; INFLUENZA A VIRUS; INHIBITORY ACTIVITY; INTRANASAL; MANNOSAMINE; MOUSE MODELS; NANOMOLAR; PRODRUGS; SIALIC ACIDS; SIALIDASE INHIBITORS; SIALIDASES;

ACIDS; ALKYLATION; CARBOXYLIC ACIDS; CELL CULTURE; ESTERIFICATION; ESTERS; ETHERS; ORGANIC POLYMERS; SYNTHESIS (CHEMICAL); VIRUSES;

ENZYME INHIBITION;

EID: 76349088084     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.67.1105     Document Type: Article

References (38)

1. Palese, P.; Compans, R. J. Gen. Virol. 1976, 33, 159.
2. Babu, Y. S.; Chand, P.; Bantia, S.; Kotian, P.; Dehghani, A.; El-Kattan, Y.; Lin T. H.; Hutchison, T. L.; Elliott, A. J.; Parker, C. D.; Ananth, S. L.; Horn, L. L.; Laver, G. W.; Montgomery, J. A. J. Med. Chem. 2000, 43, 3482.
3. Smith, P. W; Sollis, S. L.; Howes, P. D.; Cherry, P. C.; Starkey, I. D.;Cobley, K. N.; Weston, H.; Scicinski, J.; Merritt, A.; Whittington, A.; Wyatt, P.; Taylor, N.; Green, D.; Bethell, R.; Madar, S.; Fenton, R. J.; Morley, P. J.; Pateman, T.; Beresford, A. J. Med. Chem. 1998, 41, 787.
4. von Itzstein, M.; Wu, W.-Y; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Phan, T. V.; Smythe, M. L.; White, H. F.; Oliver, S. W; Colman, P. M.; Varghese, J. N.; Ryan, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M.; Penn. C. R. Nature 1993, 363, 418.
5. Kim, C. U.; Lew, W; Williams, M. A.; Liu, H.; Zhang, L.; Swaminathan, S.; Bischofberger, N.; Chen, M. S.; Mendel, D. B.; Tai, C. Y; Laver, W G.; Stevens. R. C. J. Am. Chem. Soc. 1997, 119, 681.
6. Miller, C. A.; Wang, P.; Flashner, M. Biochem. Biophys. Res. Commun. 1978, 83, 1479.
7. Smith, P. W; Starkey, I. D.; Howes, P. D.; Sollis, S, L.; Keeling, S. P.; Cherry, P. C.; von Itzstein, M.; Wu, W.-Y; Jin, B. Eur. J. Med Chem. 1996, 31, 143.
8. Murakami, M.; Ikeda, K.; Achiwa, K. Carbohydr. Res. 1996, 280, 101.
9. Andrews, D.; Jones, P.; Humber, D. PCT Int. Appl., WO9706157 (1997).
10. Taylor, N. R.; von Itzstein, M. J. Med Chem. 1994, 37, 616.
11. Honda, T.; Masuda, T.; Yoshida, S.; Arai, M.; Kobayashi, Y.; Yamashita, M. Bioorg Med Chem. Lett. 2002, 12, 1921.
12. Hartmann, M.; Christian, R.; Zbiral, E.; Synthesis of the βmethyl ketosides of 4-oxo-, 7-oxo-, and 8-oxo-N-acethlneuraminic acid and the corresponding 7, 7-and 8, 8-dimethoxy derivatives and their behavior toward CMP-sialate synthase. Liebigs Ann. Chem. 1990, 83.
13. Schreiner, E.; Christian, R.; Zbiral, E. Liebigs Ann. Chem. 1990, 93.
14. Bednarski, M. D.; Chenault, H. K.; Simon, E. S.; Whitesides, G. M. J. Am. Chem. Soc. 1987, 109, 1283.
15. Kuboki, A.; Okazaki, H.; Sugai, T.; Ohta, H. Tetrahedron 1997, 53, 2387.
16. Thomson, R. J.; von Itzstein, M. Carbohydr. Res. 1995, 274, 29.
17. Landini, D.; Penso, M. Tetrahedron Lett. 1990, 31, 7209.
18. Neu5Ac aldolase (26.6 U/mg) was purchased from TOYOBO.
19. lida, T.; Ohira, Y. PCT Int. Appl, WO9532955 (1995).
20. Sharma, M.; Bernacki, R. J.; Paul, B.; Korytnyk, W Carbohydr. Res. 1990, 198, 205.
21. Arita, H.; Fukukawa, K.; Matsushima, Y Bull. Chem. Soc. Jpn. 1972, 45, 3614.
22. Ikeda, K.; Kimura, F.; Sano, K.; Suzuki, Y.; Achiwa, K. Carbohydr. Res 1998, 312, 183.
23. Kok, G. B.; Campbell, M.; Mackey, B.; von Itzstein, M. J. Chem. Soc, Perkin Trans. 1 1996, 2811.
24. 50 value quoted is the concentration of the inhibitor required to reduce the enzymatic activity in the preparation by 50%.
25. Confluent MDCK cells were infected with the A/Yamagata/32/89 (H1N1) virus strain for 60 minutes. After removing the virus solution, pre-warmed agar media containing the compounds was added. The cells were cultured for 30-38 h. After that, the live cells were fixed and stained and visual plaques were counted.
26. Honda, T.; Masuda, T.; Yoshida, S.; Arai, M.; Kaneko, S.; Yamashita, M. Bioorg. Med. Chem. Lett. 2002, 12, 1925.
27. Zbiral, S.; Schmidt, W Liebigs Ann. Chem. 1987, 39.
28. Honda, T.; Kubo, S.; Masuda, T.; Arai, M.; Kobayashi, Y.; Yamashita, M. Bioorg. Med Chem. Lett. 2009, 19, 2938.
29. Compound (10b) and Zanamivir were administered intranasally at doses of. 0.2 μmol/kg 4 h before and 4 h, 17 h after the infection in mice. Compound (10b) was more effective than Zanamivir (2/10 survived in the 10b treated infected group while there was no survivor in the case of Zanamivir at 20 days after infection).
30. Compound (25h) and Zanamivir were administered intranasally at doses of 0.3 μmiol/kg 4 h before and 4 h, 17 h after the infection in mice. The efficacy of 25h was found to be almost same as that of Zanamivir (4/10 survived in the 25h treated infected group while there were three survivors in the case of Zanamivir at 8 days after infection).
31. Yamashita, M.; Tomozawa, T.; Kakuta, M.; Tokumitsu, A.; Nasu, H.; Kubo, S. Antimicrob. Agents Chemother. 2009, 53, 186.
32. Nakai, N.; Oitate, M.; Hoshi, M.; Kobayashi, N.; Yamamura, N.; Hirota, T. Abstr. 43rd Intersci. Conf. Antimicrob. Agents Chemother., 2003, abstr. F-1833.
33. Nakai, N.; Yoshida, S.; Tomozawa, T.; Kobayashi, N.; Yamamura, N.; Fukuda, K.; Hirota, T Abstr. 43rd Intersci. Conf. Antimicrob. Agents Chemother., 2003, abstr. F-1832.
34. Rennecke, J.; Hirota, T.; Puchler, K. Abstr. 43rd Intersci. Conf. Antimicrob. Agents Chemother., 2003, abstr. F-1834.
35. (a) Honda, T.; Yoshida, S.; Arai, M.; Masuda, T.; Yamashita, M. Bioorg. Med. Chem. Lett. 2002, 12, 1929.
36. (b) Masuda, T.; Yoshida, S.; Arai, M.; Kaneko, S.; Yamashita, M.; Honda, T.: Chem. Pharm. Bull. 2003, 51, 1386.
37. Reece, P. A.; Watson, K. G.; Wu, W.-Y.; Jin, B.; Krippner, G. Y PCT Int. Appl., WO9821243 (1998).
38. Hirabayashi, H.; Nishikawa, M.; Takakura, Y.; Hashida, M. Pharm. Res. 1996, 13, 880.