Syntheses of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues modified by α-acylaminoamido groups at the C-4 position using isocyanide-based four-component coupling and biological evaluation as inhibitors of human parainfluenza virus type 1

Chemical and Pharmaceutical Bulletin

Volumn 61, Issue 1, 2013, Pages 69-74

  Nishino, Reiko ^a   Hayakawa, Takuya ^a   Takahashi, Tadanobu ^a   Suzuki, Takashi ^a   Sato, Masayuki ^a   Ikeda, Kiyoshi ^b  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b HIROSHIMA INTERNATIONAL UNIVERSITY   (Japan)

Author keywords

4 isocyano neu5Ac2en derivative; Human parainfluenza virus type 1; Isocyanide based four component coupling; Sialic acid; Sialidase inhibitor

Indexed keywords

5 ACETYLAMINO 2,6 ANHYDRO 3,5 DIDEOXY 4 [2 (ACETYLBENZYLAMINO)ACETYLAMINO] 2 ENOIC ACID; 5 ACETYLAMINO 2,6 ANHYDRO 3,5 DIDEOXY 4 [2 (ACETYLMETHYLAMINO)ACETYLAMINO] 2 ENOIC ACID; 5 ACETYLAMINO 2,6 ANHYDRO 3,5 DIDEOXY 4 [2 (ACETYLPROPYLAMINO)ACETYLAMINO] 2 ENOIC ACID; 5 ACETYLAMINO 2,6 ANHYDRO 3,5 DIDEOXY 4 {2 [(FURAN 2 CARBONYL)METHYLAMINO] 2 ENOIC ACID; CYANIDE; METHYL 5 ACETYLAMINO 2,6 ANHYDRO 3,5 DIDEOXY 4 [2 (ACETYLBENZYLAMINO)ACETYLAMINO] 2 ENONATE; METHYL 5 ACETYLAMINO 2,6 ANHYDRO 3,5 DIDEOXY 4 [2 (ACETYLMETHYLAMINO)ACETYLAMINO] 2 ENONATE; METHYL 5 ACETYLAMINO 2,6 ANHYDRO 3,5 DIDEOXY 4 [2 (ACETYLMETHYLAMINO)BUTYRYLAMINO] 2 ENONATE; METHYL 5 ACETYLAMINO 2,6 ANHYDRO 3,5 DIDEOXY 4 [2 (ACETYLPROPYLAMINO) 2 PYRIDIN 3 YL ACETYLAMINO] D GLYCERO GALACTO NON 2 ENONATE; METHYL 5 ACETYLAMINO 2,6 ANHYDRO 3,5 DIDEOXY 4 [2 (ACETYLPROPYLAMINO)ACETYLAMINO] 2 ENONATE; METHYL 5 ACETYLAMINO 2,6 ANHYDRO 3,5 DIDEOXY 4 [2 (FORMYL METHYLAMINO)ACETYLAMINO] 2 ENONATE; METHYL 5 ACETYLAMINO 2,6 ANHYDRO 3,5 DIDEOXY 4 {2 [(FURAN 2 CARBONYL)METHYLAMINO] NON 2 ENONATE; N ACETYLNEURAMINIC ACID DERIVATIVE; SIALIDASE; SIALIDASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; FOUR COMPONENT CONDENSATION; IC 50; NONHUMAN; ONE POT SYNTHESIS; PARAINFLUENZA VIRUS 1;

ANTIVIRAL AGENTS; HUMANS; N-ACETYLNEURAMINIC ACID; NEURAMINIDASE; PARAINFLUENZA VIRUS 1, HUMAN; RESPIROVIRUS INFECTIONS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84872181185     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.c12-00834     Document Type: Article

References (23)

1. Collins P. L., Chanock R. M., McIntosh K., "Fields Virology," ed. by Fields B. N., Knipe, D. M., Howley, P. M., Lippincott-Raven, Philadelphia, 1996, pp. 1205-1241.
2. Murphy B. R., "Infectious Diseases," ed. by Gorbach S. L., Bartlett J. G., Blacklow N. R., W. B. Saunders Company, Philadelphia, 1998, pp. 2125-2131.
3. Henrickson K. J., Clin. Microbiol. Rev., 16, 242-264 (2003).
4. Schauer R., Kelm S., Reuter G., Roggentin P., Shaw L., "Biology of the Sialic Acids," ed. by Rosenberg A., Plenum Press, New York, 1995.
5. Wilson J. C., Thomson R. J., Dyason J. C., Florio P., Quelch K. J., Abo S., von Itzstein M., Tetrahedron Asymmetry, 11, 53-73 (2000).
6. Ikeda K., Sato M., Torisawa Y., Curr. Med. Chem.-Anti-infective Agents, 3, 339-350 (2004).
7. von Itzstein M., Wu W.-Y., Kok G. B., Pegg M. S., Dyason J. C., Jin B., Van Phan T., 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, 363, 418-423 (1993).
8. Merson J. R., Hull R. A., Estes M. K., Kasel J. A., Virology, 167, 97-105 (1988).
9. Varsanyi T. M., Kövamees J., Norrby E., J. Gen. Virol., 72, 89-95 (1991).
10. Alymova I. V., Taylor G., Takimoto T., Lin T. H., Chand P., Babu Y. S., Li C., Xiong X., Portner A., Antimicrob. Agents Chemother., 48, 1495-1502 (2004).
11. Ikeda K., Sano K., Ito M., Saito M., Hidari K., Suzuki T., Suzuki Y., Tanaka K., Carbohydr. Res., 330, 31-41 (2001).
12. Suzuki T., Ikeda K., Koyama N., Hosokawa C., Kogure T., Takahashi T., Jwa Hidari K. I., Miyamoto D., Tanaka K., Suzuki Y., Glycoconj. J., 18, 331-337 (2001).
13. Ikeda K., Sato K., Nishino R., Aoyama S., Suzuki T., Sato M., Bioorg. Med. Chem., 16, 6783-6788 (2008).
14. Ikeda K., Sato K., Kitani S., Suzuki T., Maki N., Suzuki Y., Sato M., Bioorg. Med. Chem., 14, 7893-7897 (2006).
15. Sato K., Ikeda K., Suzuki T., Aoyama S., Maki N., Suzuki Y., Sato M., Tetrahedron, 63, 7571-7581 (2007).
16. Rostovtsev V. V., Green L. G., Fokin V. V., Sharpless K. B., Angew. Chem., Int. Ed., 41, 2596-2599 (2002).
17. Dömling A., Chem. Rev., 106, 17-89 (2006).
18. Yoo E. J., Bae I., Cho S. H., Han H., Chang S., Org. Lett., 8, 1347-1350 (2006).
19. Nishino R., Ikeda K., Hayakawa T., Takahashi T., Suzuki T., Sato M., Bioorg. Med. Chem., 19, 2418-2427 (2011).
20. Shaabani A., Maleki A., Mofakham H., Khavasi H. R., J. Comb. Chem., 10, 323-326 (2008).
21. Dömling A., Ugi I., Angew. Chem., Int. Ed., 39, 3168-3210 (2000).
22. Schreiner E., Zbiral E., Kleineidam R. G., Schauer R., Liebigs Ann. Chem., 1991, 129-134 (1991).
23. Prosperi D., Ronchi S., Lay L., Rencurosi A., Russo G., Eur. J. Org. Chem., 2004, 395-405 (2004).