Syntheses of large-ring bis-indolic dilactams

Tetrahedron Letters

Volumn 40, Issue 9, 1999, Pages 1685-1688

  Charlet Fagnère, Catherine ^a   Jiang, Wei Qun ^a   Laronze, Jean Yves ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

LACTAM;

ARTICLE; DRUG BIOAVAILABILITY; DRUG CONFORMATION; DRUG SOLUBILITY; DRUG SYNTHESIS; LIPOPHILICITY; MOLECULAR SIZE; STRUCTURE ANALYSIS;

EID: 0033605302     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00065-9     Document Type: Article

References (19)

1. 3. Dietrich, B.; Lehn, J.M.; Sauvage, J.P.; Blauzat, J. Tetrahedron 1973, 29, 1629-1645.
2. 4. Dietrich, B.; Lehn, J.M.; Sauvage, J.P. Tetrahedron 1973, 29, 1647-1667.
3. 5. Conn, M.M.; Rebek Jr., J. Chem. Reviews 1997, 97, 1647-1668.
4. 6. Gutte, B. "Peptides. Synthesis, Structures and Applications". Academic Press, New-York, 1995.
5. 7. Charlet-Fagnere, C.; Laronze, J.; Laronze, J.Y.; Toupet, L.; Vistelle, R.; Lamiable, D.; Mouchard, C.; Renard, P.; Adam, G. Bull. Soc. Chim. Fr. 1996, 133, 39-50.
6. 8. Garratt, P.J.; Travard, S.; Vonhoff, S.; Tsotinis, A.; Sugden, D. J. Med. Chem. 1996, 39, 1797-1805 and ref. cited.
7. 3N (1 equiv) at r.t. (26%-92%, not optimized).
8. 2-N), 46.9 (C-3′), 59.9 (C-2′)[COSY].
9. 11. In these cyclizations only one isomer was observed. The value of the coupling constant between 2′-H and 3′-H varies from 4.5 Hz (8a, n=1) to 9 Hz (8a, n=6), therefore it does not allow to conclude on the relationship between them. A conformational study by molecular dynamics (Insight II) of these compounds revealed that the length of the diamide chain does not influence notably the relative orientation of the aromatic systems: the dihedral angle between C2′-H and C3′-H would be about 140° for a trans relationship, and around 20° for a cis one. The observed coupling constants are consistent with a trans system.
10. 12. Bach, R.D.; Mintcheva, I.; Kronenberg, W.J.; Schlegel, H.B. J. Org. Chem. 1993, 58, 6135-6138.
11. 13. Biswas, K.M.; Jackson, A.H. J. Chem. Soc. Perkin Trans I 1989, 1981-1986.
12. 14. Alvares, M.; Salas, M. Heterocycles 1991, 32, 1391-1394.
13. 15. Abe, N.; Enoki, N.; Nakakita, Y.; Uchida, H.; Nakamuva, T.; Munekata, N. J. Antibiotics 1993, 46, 1678-1681.
14. 13C NMR: 50,3 (C-3), 63.3 (C-2), 127.0 (C-6′).
15. 3OD): 86.9 (C-3′).
16. 125I-melatonin of his receptors in homogenate of pars tuberalis of sheep brain.
17. 20. Fleming, B.I.; Harley-Mason, J. J. Chem. Soc. 1966, 4, 425.
18. 3): 153.7 (C-5). EIMS m/z 174, base peak.
19. 2 568.3792 568.3777 171.7 * 135.4 * 136.6 *