First total synthesis of Mer-N5075A and a diastereomeric mixture of α and β-MAPI, new HIV-I protease inhibitors from a species of Streptomyces

Tetrahedron

Volumn 57, Issue 20, 2001, Pages 4311-4321

  Konda, Yaeko ^a   Takahashi, Yukihiro ^a   Arima, Shiho ^a   Sato, Noriko ^a   Takeda, Kazuyoshi ^a   Dobashi, Kazuyuki ^b   Baba, Masanori ^c   Harigaya, Yoshihiro ^a  

^a KITASATO UNIVERSITY   (Japan)

^b MERCIAN CORPORATION   (Japan)

^c Kagoshima University   (Japan)

Author keywords

HIV I protease inhibitor; Streptomyces species; Syntheses; Tetrapeptide; Ureido moiety

Indexed keywords

GE 20372A; GE 20372B; MER N50752A; MER N5075A; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; INHIBITION KINETICS; MAPI; PRIORITY JOURNAL; PROTEINASE INHIBITION; REACTION ANALYSIS; STREPTOMYCES; T LYMPHOCYTE;

HUMAN IMMUNODEFICIENCY VIRUS 1; STREPTOMYCES;

EID: 0035858718     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)00323-4     Document Type: Article

References (23)

1. Fink D.M., Bores G.M., Effiand R.C., Huger F.P., Kurys B.E., Rush D.K., Selk D.E. J. Med. Chem. 38:1995;3645.
2. Sugimoto H., Iimura Y., Yamanishi Y., Yamatsu K. J. Med. Chem. 38:1995;4821.
3. Omura S., Kuno F., Otoguro K., Sunazuka T., Shiomi K., Masuma R., Iwai Y. J. Antibiot. 48:1995;745.
4. Cohen J. Science. 272:1996;1182.
5. Caring J.C., Duncan I.B., Hockely D., Grief C., Roberts N.A., Mills J.S. Antiviral. Res. 16:1991;295.
6. Danner S.A., Carr A., Leonard J.M., Lehman L.M., Gudiol F., Gonzales J., Raventos A., Rubio R., Bouza E., Pintado V., Aguado A.G., de Lomas J.G., Delgado R., Borleffs J.C.C., Hsu A., Valdes J.M., Boucher C.A.B., Cooper D.A. N. Eng. J. Med. 33:1995;1528.
7. Kaneto R., Chiba H., Dobashi K., Kojima I., Sasaki K., Shibamoto N., Nishida H., Okamoto R., Akagawa H., Mizuno S.J. J. Antibiotics. 46:1993;1622.
8. Murano S., Watanabe T. Agri. Biol. Chem. 41:1977;1313.
9. Murano S., Watanabe T. Agri. Biol. Chem. 42:1978;2209.
10. Watanabe T., Fukuhara K., Murano S. Tetrahedron Lett. 46:1979;625.
11. Watanabe T., Murano S. Agri. Biol. Chem. 43:1979;243.
12. Shin-Watanabe T., Fukuhara K., Murano S. Tetrahedron. 38:1982;1775.
13. Stefanelli S., Cavaletti E., Sarubbi E., Ragg L., Colombo L., Selva E.J. Antibiotics. 48:1995;332.
14. Konda Y., Takahashi Y., Mita H., Takeda K., Harigaya Y. Chem. Lett. 1997;345.
15. Majer P., Randad R.S. J. Org. Chem. 59:1994;1937.
16. Leung M.K., Lai J.L., Lau K.H., Yu H.H., Hsiao H.J. J. Org. Chem. 61:1996;4175.
17. Zhang X., Rodrigues J., Evans L., Hinkle B., Ballantyne L., Pena M. J. Org. Chem. 62:1997;6420.
18. Eckert H., Foster B. Angew. Chem. Int. Ed. Engl. 26:1987;894.
19. Ogura H., Kobaya T., Shimizu K., Kawabe K., Takeda K. Tetrahedron Lett. 20:1979;4745.
20. Takeda K., Akiyama A., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigata Y. Synthesis. 1994;1063.
21. Goodacre J., Ponsford R.J., Stirling I. Tetrahedron Lett. 16:1975;3609.
22. Koenig W., Geiger R. Chem. Ber. 103:1970;788.
23. Nishimura O., Fujimo M. Chem. Pharm. Bull. 24:1976;1568.