Convenient synthesis of a 2,3,6-tristhiazolyl-substituted pyridine skeleton [fragment A-C] of a macrocyclic antibiotic, GE 2270 A

Heterocycles

Volumn 53, Issue 4, 2000, Pages 765-770

  Okumura, Kazuo ^a   Suzuki, Taishi ^a   Shin, Chung Gi ^a  

^a KANAGAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 {2 [(1 AMINO 2 HYDROXY 2 PHENYL)ETHYL]THIAZOL 4 YL} THIAZOL 4 YL)PYRIDINE DERIVATIVE; GE 2270A; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0034177588     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-8818     Document Type: Article

References (22)

1. a) E. Selva, G. Beretta, N. Montanini, G. S. Saddler, L. Gastaldo, P. Ferrari, R. Lorenzetti, P. Landini, F. Ripamonti, B. P. Goldstein, M. Berti, L. Montanaro, and M. Denaro, J. Antibiot., 1991, 44, 693.
2. b) J. Kettenring, L. Colombo, P. Ferrari, P. Tavecchia, M. Nebuloni, K. Vekey, G. G. Gallo, and E. Selva, J. Antibiot., 1991, 44, 702.
3. c) P. Tavecchia, P. Gentili, M. Kurz, C. Sottani, R. Bonfichi, S. Lociuro, and E. Selva, J. Antibiot., 1994, 47, 1564.
4. C. Shin, K. Okumura, M. Shigekuni, and Y. Nakamura, Chem. Lett., 1998, 139; K. Okumura, Y. Nakamura, and C. Shin, Bull. Chem. Soc. Jpn., 1999, 72, 1561.
5. C. Shin, K. Okumura, M. Shigekuni, and Y. Nakamura, Chem. Lett., 1998, 139; K. Okumura, Y. Nakamura, and C. Shin, Bull. Chem. Soc. Jpn., 1999, 72, 1561.
6. K. Okumura, A. Ito, D. Yoshioka, and C. Shin, Heterocycles, 1998, 48, 1319.
7. K. Okumura, H. Saito, C. Shin, K. Umemura, and J. Yoshimura, Bull. Chem. Soc. Jpn., 1998, 71, 1863.
8. K. Okumura, M. Shigekuni, Y. Nakamura, and C. Shin, Chem. Lett., 1996, 1025.
9. A. M. P. Koskinen, H. Hassila, V. T. Myllymaki, and K. Rissanen, Tetrahedron Lett., 1995, 36, 5619.
10. 3 x 3), 4.38 (br s, 1H, α-H), 5.06 (d, 1H, β-H, 7=6.1 Hz), 5.97 (br s, 1H, NH), 7.15-7.56 (m, 15H, Ph x 3), 12.58 (s, 1H, COOH).
11. 3 x 3), 4.78-4.81 (m, 1H, NHCH), 5.19 (d, 1H, CHPh, 7=4.9 Hz), 5.85 (br s, 1H, NH), 7.07-7.56 (m, 15H, Ph x 3), 9.08 (br s, 1H, NH), 9.55 (br s, 1H, NH).
12. 2, J=7.3 Hz), 5.12-5.15 (m, 1H, NHCH), 5.20 (d, 1H, CHTh, J=8.6 Hz), 7.10-7.38 (m, 16H, Ph x 3 and NH), 8.31 (s, 1H, thiazole ring H).
13. 1H NMR spectral data of 10, 15, and 22, it was found that no racemization has taken place during the formation of new thiazole and oxazoline rings.
14. 3 x 3), 5.10-5.15 (m, 2H, α-H and β-H), 7.15-7.54 (m, 18H, Ph x 3 and NH x 3), 8.10 (s, 1H, thiazole ring H).
15. 3 x 3), 5.10-5.15 (m, 2H, NHCH and CHPh), 7.09-7.39 (m, 16H, Ph x 3 and NH), 8.30 (s, 1H, thiazole ring H), 9.26 (br s, 1H, NH), 9.94 (br s, 1H, NHCH).
16. 2), 6.95-7.36 (m, 16H, NH and Ph x 3), 7.70-7.72 (m, 2H, thiazole ring H and pyridine ring H), 8.17 and 8.53 (each s, 2H, thiazole ring H), 8.36 (d, 1H, pyridine ring H).
17. 2), 7.09-8.03 (m, 22H, Ph x 4 and thiazole ring H x 2), 8.25, 8.48 (each s, 2H, thiazole ring H x 2), 8.36, 8.43 (each d, 2H, pyridine ring H, J=8.2 Hz).
18. Y. Hamada, M. Shibata, T. Sugiura, S. Kato, and T. Shioiri, J. Org. Chem., 1987, 52, 1252.
19. BOP=(Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; B. Castro, J. R. Dormoy, B. Dourtoglou, G. Evin, C. Selve, and J. C. Ziegler, Synthesis, 1976, 751.
20. 2, J=7.0 Hz), 5.29 (d, 1H, CHPh, J=7.3 Hz), 5.47-5.50 (m, 1H, NHCH), 6.69 (br s, 1H, Gly's NH), 7.14-7.43 (m, 16H, Ph x 3 and COOH), 7.70, 8.18, 8.23, 8.55 (each s, 4H, thiazole ring H x 4), 7.90-8.05 (m, 1H, NHCH), 8.41-8.50 (m, 2H, pyridine ring H x 2).
21. 2), 7.21-7.31 (m, 5H, Ph), 7.78, 7.81, 8.27 (each s, 3H, thiazole ring H x 3), 8.37-8.60 (m, 5H, pyridine ring H x 2, thiazole ring H, and NH x 2).
22. +.