Synthesis of 9,11-ethano-13,15-isoxazolinoprostanoids, PGH analogs

Russian Journal of Organic Chemistry

Volumn 39, Issue 8, 2003, Pages 1089-1094

  Bondar', N F ^a   Isaenya, L P ^a   Skupskaya, R V ^a   Lakhvich, F A ^a  

^a INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

Author keywords

[No Author keywords available]

Indexed keywords

METHYL 7 OXO 9,11 ETHANO 12 (5 PENTYL 4,5 DIHYDRO 3 ISOXAZOLYL) 13,14,15,16,17,18,19,20 OCTANORPROSTANATE; METHYL 7 OXO 9,11 ETHANO 12 (5 PHENYL 4,5 DIHYDRO 3 ISOXAZOLYL) 13,14,15,16,17,18,19,20 OCTANORPROSTANATE; METHYL 7 OXO 9,11 ETHANO 12 (5 PHENYL 4,5 DIHYDRO 3 ISOXAZOLYL) 2,13,14,15,16,17,18,19,20 NONANORPROSTANATE; METHYL 7 OXO 9,11 ETHANO 12 [5 (1 IMIDAZOLYL) 4,5 DIHYDRO 3 ISOXAZOLYL] 2,13,14,15,16,17,18,19,20 NONANORPROSTANATE; METHYL 7 OXO 9,11 ETHANO 12 [5 (2 OXOPYRROLIDINO) 4,5 DIHYDRO 3 ISOXAZOLYL] 2,13,14,15,16,17,18,19,20 NONANORPROSTANATE; METHYL 7 OXO 9,11 ETHANO 12 [5 (2 PYRIDYL) 4,5 DIHYDRO 3 ISOXAZOLYL] 2,13,14,15,16,17,18,19,20 NONANORPROSTANATE; METHYL 7 OXO 9,11 ETHANO 12 [5 (4 CHLOROPHENOXYMETHYL) 4,5 DIHYDRO 3 ISOXAZOLYL] 13,14,15,16,17,18,19,20 OCTANORPROSTANATE; METHYL 7 OXO 9,11 ETHANO 12 [5 (4 CHLOROPHENOXYMETHYL) 4,5 DIHYDRO 3 ISOXAZOLYL] 2,13,14,15,16,17,18,19,20 NONANORPROSTANATE; METHYL 7 OXO 9,11 ETHANO 12 [5 (4 PYRIDYL) 4,5 DIHYDRO 3 ISOXAZOLYL] 2,13,14,15,16,17,18,19,20 NONANORPROSTANATE; PROSTAGLANDIN DERIVATIVE; PROSTANOIC ACID DERIVATIVE; PROSTANOID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 3543010770     PISSN: 10704280     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:RUJO.0000010175.39145.9a     Document Type: Article

References (24)

1. Leeney, T.J., Marsham, P.R., Ritchi, G.A.F., and Senior, M.W., Prostaglandins., 1976, vol. 11, p. 953; Wilson, N.H., Jones, R.L., Marr, C.G., and Muir, G., Eur. J. Med. Chem., 1988, vol. 23, p. 359; Miftakhov, M.S., Valeev, F.A., Gaisina, I.N., Shitikova, O.V., Sultanmuratova, V.R., and Tolstikov, G.A., Zh. Org. Khim., 1993, vol. 29, p. 1122.
2. Leeney, T.J., Marsham, P.R., Ritchi, G.A.F., and Senior, M.W., Prostaglandins., 1976, vol. 11, p. 953; Wilson, N.H., Jones, R.L., Marr, C.G., and Muir, G., Eur. J. Med. Chem., 1988, vol. 23, p. 359; Miftakhov, M.S., Valeev, F.A., Gaisina, I.N., Shitikova, O.V., Sultanmuratova, V.R., and Tolstikov, G.A., Zh. Org. Khim., 1993, vol. 29, p. 1122.
3. Leeney, T.J., Marsham, P.R., Ritchi, G.A.F., and Senior, M.W., Prostaglandins., 1976, vol. 11, p. 953; Wilson, N.H., Jones, R.L., Marr, C.G., and Muir, G., Eur. J. Med. Chem., 1988, vol. 23, p. 359; Miftakhov, M.S., Valeev, F.A., Gaisina, I.N., Shitikova, O.V., Sultanmuratova, V.R., and Tolstikov, G.A., Zh. Org. Khim., 1993, vol. 29, p. 1122.
4. Kondratenkova, E.M., Kuz'mitskii, B.B., Nasek, V.M., Katok, Ya.M., Chernikhova, T.V., and Koroleva, E.V., Vestsi National Akad. Nauk Belarusi, Ser. Khim., 1999, no. 4, 58;
5. Kuz'mitskii, B.B., Konoplya, N.A., Lyubin, G.S., Koroleva, E.V., Katok, Ya.M., and Chernikhova, T.V., Vestsi National Akad. Nauk Belarusi, Ser. Khim., 2001, no. 1, p. 68;
6. Bondar', N.F., Kuz'mitskii, B.B., Golubeva, M.B., Konoplya, N.A., and Shafranskaya, G.A., Vestsi Akad. Nauk BSSR, Ser. Biyal., 1990, no. 4, p. 97;
7. Bondar, N.F., Kuz'mitskii, B.B., and Malaeva, L.P., Vestsi Akad. Nauk BSSR, Ser. Khim., 1991, no. 3, p. 52;
8. Kuz'mitskii, B.B., Malaeva, L.P., Romanova, V.N., Skupskaya, R.V., and Bondar', N.F., Vestsi Akad. Nauk BSSR, Ser. Khim., 1992, no. 3, p. 87.
9. Kametani, T., Suzuki, T., Kamada, S. et al., J. Chem. Soc., 1981, p. 3101; Lieb, F., Niewζhner, U., and Wendisch, D., Liebigs Ann. Chem., 1987, p. 607.
10. Kametani, T., Suzuki, T., Kamada, S. et al., J. Chem. Soc., 1981, p. 3101; Lieb, F., Niewζhner, U., and Wendisch, D., Liebigs Ann. Chem., 1987, p. 607.
11. Larock, R.C. and Baby, S., Tetrahedron, 1987, vol. 43, p. 2013;
12. Larock, R.C., Hsu, M.H., and Harayanan, K., Tetrahedron, 1987, vol. 43, p. 2891;
13. Larock, R.C. and Narayaman, K., Tetrahedron, 1988, vol. 44, p. 6995.
14. Barraclough, P., Tetrahedron Lett., 1980, p. 1897; Narisada, M., Ohtani, M., Watanabe, F. et al., J. Med. Chem., 1988, vol. 31, p. 1848.
15. Barraclough, P., Tetrahedron Lett., 1980, p. 1897; Narisada, M., Ohtani, M., Watanabe, F. et al., J. Med. Chem., 1988, vol. 31, p. 1848.
16. Bondar', N.F., Omel'chenko, T.N., Skupskaya, R.V., and Lakhvich, F.A., Zh. Org. Khim., 1989, vol. 35, p. 206; Bondar', N.F., Skupskaya, R.V., Levchenko, V.K., and Lakhvich, F.A., Vestsi Akad. Nauk BSSR, Ser. Khim., 1991, no. 3, p. 48; Skupskaya, R.V., Bondar', N.F., and Lakhvich, F.A., Vestsi Akad. Nauk BSSR, Ser. Khim., 1995, no. 1, p. 65.
17. Bondar', N.F., Omel'chenko, T.N., Skupskaya, R.V., and Lakhvich, F.A., Zh. Org. Khim., 1989, vol. 35, p. 206; Bondar', N.F., Skupskaya, R.V., Levchenko, V.K., and Lakhvich, F.A., Vestsi Akad. Nauk BSSR, Ser. Khim., 1991, no. 3, p. 48; Skupskaya, R.V., Bondar', N.F., and Lakhvich, F.A., Vestsi Akad. Nauk BSSR, Ser. Khim., 1995, no. 1, p. 65.
18. Bondar', N.F., Omel'chenko, T.N., Skupskaya, R.V., and Lakhvich, F.A., Zh. Org. Khim., 1989, vol. 35, p. 206; Bondar', N.F., Skupskaya, R.V., Levchenko, V.K., and Lakhvich, F.A., Vestsi Akad. Nauk BSSR, Ser. Khim., 1991, no. 3, p. 48; Skupskaya, R.V., Bondar', N.F., and Lakhvich, F.A., Vestsi Akad. Nauk BSSR, Ser. Khim., 1995, no. 1, p. 65.
19. Kozikowski, A.P. and Adamczyk, M., Tetrahedron Lett., 1982, vol. 23, p. 3123.
20. Weygand-Hilgetag Organisch-chemische Experimentierkunst, Hilgetag, G. and Martini, A., Eds., Leipzig: Johann Ambrosius Barth, 1964, 3rd ed. Translated under the title Metody eksperimenta v organicheskoi khimii, Moscow: Khimiya, 1968.
21. Weygand-Hilgetag Organisch-chemische Experimentierkunst, Hilgetag, G. and Martini, A., Eds., Leipzig: Johann Ambrosius Barth, 1964, 3rd ed. Translated under the title Metody eksperimenta v organicheskoi khimii, Moscow: Khimiya, 1968.
22. Elder, J.S., Mann, J., and Walsh, E.B., Tetrahedron, 1985, vol. 41, p. 3117.
23. Lakhvich, F.A., Koroleva, E.V., and Akhrem, A.A., Khim. Geterotsikl. Soed., 1989, p. 435.
24. Gordon, A.J. and Ford, R.A., The Chemist's Companion, New York: Wiley, 1972.