Molecular library obtained by allene insertion into the Pd-C bond of cyclopalladated complexes: Biological and pharmacological evaluation

European Journal of Organic Chemistry

Volumn , Issue 8, 2004, Pages 1724-1731

  Sirlin, Claude ^a   Chengebroyen, Jaganaiden ^a   Konrath, Renato ^a   Ebeling, Günther ^a   Raad, Imad ^a   Dupont, Jairton ^b   Paschaki, Marie ^a   Kotzyba Hibert, Florence ^a   Harf Monteil, Colette ^a   Pfeffer, Michel ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

Author keywords

Allenes; Antibiotics; N heterocycles; Nicotinic receptor; Palladium

Indexed keywords

2,2 DIMETHYL 3 METHYLENENAPHTHO[DEF]QUINOLIZINIUM; ALLENE DERIVATIVE; CARBON; CHOLINERGIC RECEPTOR; HETEROCYCLIC COMPOUND; NICOTINIC RECEPTOR; PALLADIUM COMPLEX; QUINOLIZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; COMPLEX FORMATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SENSITIVITY; DRUG SYNTHESIS; MOLECULAR INTERACTION; NONHUMAN; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 4544245779     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300776     Document Type: Article

References (57)

1. [1a] J. Spencer, M. Pfeffer, Advances in Metallo-organic Chemistry 1998, 6, 103.
2. [1b] M. Pfeffer, Pure and Applied Chemistry 1992, 64, 335.
3. [1c] M. Pfeffer, Recl. Trav. Chim. Pays-Bas 1990, 109, 567.
4. [2a] J. Chengebroyen, M. Pfeffer, C. Sirlin, Tetrahedron Lett. 1996, 37, 7263.
5. [2b] J. J. H. Biederen, H. W. Frühauf, H. Hiemstra, K. Vrieze, M. Pfeffer, Tetrahedron Lett. 1998, 39, 4111.
6. [2c] J. Chengebroyen, M. Linke, M. Robitzer, C. Sirlin, M. Pfeffer, J. Organomet. Chem. 2003, 687, 313.
7. [3a] P. A. van der Schaaf, J.-P. Sutter, M. Grellier, G. P. M. van Mier, A. L. Spek, G. van Koten, M. Pfeffer, J. Am. Chem. Soc. 1994, 116, 5134.
8. [3b] M. Grellier, M. Pfeffer, G. van Koten, Tetrahedron Lett. 1994, 35, 2877.
9. [3c] M. Pfeffer, J.-P. Sutter, A. De Cian, J. Fischer, Inorg. Chim. Acta 1994, 220, 115.
10. [3d] M. Grellier, M. Pfeffer, J. Organomet. Chem. 1997, 548, 301.
11. R. Zimmer, C. U. Dinesh, E. Nandanan, F. Kahn, Chem. Rev. 2000, 100, 3067.
12. [5a] R. C. Larock, N. G. Berrios-Pena, C. A. Fried, J. Org. Chem. 1991, 50, 2615.
13. [5b] R. C. Larock, Y. He, W. W. Leong, X. Han, M. D. Refvik, J. M. Zenner, J. Org. Chem. 1998, 63, 2154.
14. [5c] R. C. Larock, C. Tu, P. Pace, J. Org. Chem. 1998, 63, 6859.
15. [5d] E. Desarbre, J.-Y. Merour, Tetrahedron Lett. 1996, 37, 43.
16. [5e] J. J. H. Diederen, R. W. Sinkeidam, H. W. Frühauf, H. Hiemstra, K. Vrieze, Tetrahedron Lett. 1999, 40, 4255.
17. [5f] R. Grigg, W. S. MacLachlan, D. T. MacPherson, V. Sridharan, S. Suganthan, M. Thorton-Pett, J. Zhang, Tetrahedron 2000, 56, 6585.
18. [5g] K. Hiroi, Y. Hiratsuka, K. Watanabe, I. Abe, F. Kato, M. Hiroi, Tetrahedron Assym. 2002, 13, 1351.
19. R. N. Jones, Chest 2001, 119, 397S.
20. F. Hucho, C. Weise, Angew. Chem. Int. Ed. 2001, 40, 3100.
21. A. G. Engel, K. Ohno, S. M. Sine, Muscle Nerve 2003, 27, 4.
22. M. W. M. Holladay, M. J. Dart, J. K. Lynch, J. Med. Chem. 1997, 40, 4169.
23. [10a] M. Pfeffer. Inorg Synth 1989 26, 211.
24. [10b] A. C. Cope, E. C. Friedrich, J. Am. Chem. Soc. 1968, 90, 909.
25. [10c] T. Komatsu, M. Nonoyama, J. Inorg. Nucl. Chem. 1977, 39, 1161.
26. [10d] N. Beydoun, PhD thesis, Louis Pasteur University, Strasbourg, France, 1990.
27. [10e] F. Maassarani, M. Pfeffer, G. Le Borgne, Organometallics 1987, 6, 2029.
28. J. Dupont, N. R. Basso, M. R. Meneghetti, R. A. Konrath, R. Burrow, M. Horner, Organometallics 1997, 16, 2386.
29. [12a] K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 4467.
30. [12b] A. Arcadi, S. Cacchi, F. Marinelli, Tetrahedron Lett. 1989, 30, 2581.
31. [12c] A. P. Melissaris, M. H. Litt, J. Org. Chem. 1992, 57, 6998.
32. [13a] Hoffman-La Roche, US Patent 2470109, 1947.
33. [13b] L. Wittig, Justus Liebig Ann. Chem. 1954, 589, 55, 71.
34. [13c] D. W. Brown, M. Sainsbury, S. F. Dyke, W. G. D. Lagton, Tetrahedron 1971, 27, 4519.
35. [13d] F Eiden, U. Rehse, Chem. Ber. 1974, 107, 1057.
36. [13e] F. Eiden, C. Herdeis, Arch. Pharm. 1976, 309, 425.
37. [13f] S. M. Makin, A. I. Pomoaev, J. Org. Chem. USSR (Engl. Transl.) 1981, 17, 2020.
38. [13g] T. Lorand, J. Deli, D. Szabo, A. Foeldesi, A. Zschunke, Pharmazie 1985, 40, 536.
39. [14a] B Akermark, S. Hansson, B. Krakenberger, A. Vitagliano, K. Zetterberg, Organometallics 1984, 3, 679.
40. [14b] T. Cuvigny, M. Julia, C. Rolando, J. Organomet. Chem. 1985, 285, 395.
41. [15a] Performance standards for antimicrobial disk susceptibility tests, 6th ed. in Approved Standard 1997, 17, 7.
42. [15b] J. Freney, F. Renaud, W. Hansen, C. Bollet, Précis de bactériologie clinique (Ed.: ESKA), 2000, 565, 575.
43. [16a] Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, 4th ed. in Approved Standard 1997, 17, 9.
44. [16b] P. Courvalin, F. Goldstein, A. Philippen, J. Sirot, L'antibiogramme 1985, 191.
45. MIC is the lowest concentration of antimicrobial agent that completely inhibits growth of the organism in the tubes as detected by the unaided eye.
46. MBC is obtained for a decrease of at least 4 log units of the inoculum percentage of viable bacteria.
47. K. Brejc, W. J. van Dijk, R. V. Klaassen, M. Schuurmans, J. van der Dost, A. B. Smit, T. K. Sixma, Nature 2001, 411, 269.
48. C. E. Spivak, J. A. Waters, R. S. Aronstam, Mol. Pharmacol. 1989, 36, 177.
49. T. Grutter, M. Goeldner, F. Kotzyba-Hibert, Biochemistry 1999, 38, 7476.
50. A. T. Eldefrawi, E. R. Miller, D. L. Murphy, M. E. Eldefrawi, Mol. Pharmacol. 1982, 22, 72.
51. G. B. Heisig, H. M. Davis, J. Am. Chem. Soc. 1935, 57, 339.
52. B. D. Hosangadi, R. H. Dave, Tetrahedron Lett. 1996, 37, 6375.
53. [25a] General technical conditions for dilution methods in Communiqué 2000-01, 3.
54. [25b] Microbiological titration of antibiotics in Pharmacopée Française 1984, V.2.2.1.
55. T. Saitoh, J.-P. Changeux, Eur. J. Biochem. 1980, 105, 51.
56. J. Schmidt, M. A. Raftery, Anal. Biochem. 1973, 52, 349.
57. G. L. Paterson, Anal. Biochem. 1977, 83, 346.