Use of polyfunctionalized pyridazines as reactive species for building chemical diversity

Current Organic Chemistry

Volumn 10, Issue 3, 2006, Pages 277-295

  Bourguignon, J J ^a   Oumouch, S ^a   Schmitt, M ^a  

^a CNRS   (France)

Author keywords

Anti angiogenic; Benzodiazepine receptor; Diels Alder reactions; Pyridazine drugs; Sonogashira reaction; Vicarious nucleophilic substitution

Indexed keywords

AMINATION; AMINES; BIOCHIPS; CHEMICAL BONDS; SCAFFOLDS;

ANTI-ANGIOGENIC; BENZODIAZEPINE RECEPTOR; BENZODIAZEPINES; CROSS COUPLING REACTIONS; DIELS-ALDER REACTION; PALLADIUM CROSS-COUPLING; PYRIDAZINE; PYRIDAZINE DRUG; SONOGASHIRA REACTIONS; VICARIOUS NUCLEOPHILIC SUBSTITUTIONS;

REGIOSELECTIVITY;

3 AMINOPYRIDAZINE DERIVATIVE; 3,4,5 TRICHLOROPYRIDAZINE DERIVATIVE; 3,4,5,6 TETRACHLOROPYRIDAZINE DERIVATIVE; 3,4,6 TRICHLOROPYRIDAZINE DERIVATIVE; 3,6 DICHLOROPYRIDAZINE DERIVATIVE; AMIDE; ANGIOGENESIS INHIBITOR; AZELASTINE; BROMINE; CARBONIC ACID; CARDIOVASCULAR AGENT; CENTRAL NERVOUS SYSTEM AGENTS; CHLORINE DERIVATIVE; CHOLINESTERASE INHIBITOR; CYCLOOXYGENASE 2 INHIBITOR; HALOGEN; HISTAMINE H1 RECEPTOR ANTAGONIST; IMMUNOLOGIC AGENT; IODINE; LEWIS ACID; LIGAND; MITOGEN ACTIVATED PROTEIN KINASE P38 INHIBITOR; PALLADIUM; PYRIDAZINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; ZARDAVERINE;

ALKYLATION; AMINATION; ARYLATION; CATALYST; CHEMICAL REACTION; COMBINATORIAL CHEMISTRY; CROSS COUPLING REACTION; ELECTRON; HALOGENATION; REVIEW; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 33645970769     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527206775473878     Document Type: Review

References (102)

1. (a) Frank, H.; Heinisch, G. In Pharmacologically Active Pyridazine Part1, Progress in Medicinal Chemistry, Ed. Elsevier Science B. V: Amsterdam, 1990, 271.
2. (b) Frank, H.; Heinisch, G. In Pharmacologically Active Pyridazines Part 2, Progress in Medicinal chemistry; Ed. Elsevier Science B. V: Amsterdam, 1992, 141.
3. Basile, A. S.; Lippa, A. S.; Skolnick, P. Eur. J. Pharmacol 2004, 500, 441.
4. Schudt, C., Winder, S.; Muller, B.; Ukena, D. J. W. Biochem. Pharmacol. 1991, 42, 153.
5. McIntyre C. J.; Ponticello G. S.; Liverton N. J.; O'Keefe S. J.; O'Neill E. A.; Pang M.; Schwartz C. D; Claremon D. Bioorg. Med. Chem. Lett. 2002, 12, 689.
6. Velentza, A. V.; Schumacher, A. M.; Watterson, D. M. Pharmacology & Therapeutics 2002, 93, 217.
7. Li, C. S.; Brideau, C.; Chan, C. C.; Savoie, C.; Claveau, D.; Charleson, S.; Gordon, R.; Greig, G.; Gauthier, J. Y.; Lau, C. K.; Riendeau, D.; Therien, M.; Wong, E.; Prasit, P. Bioogr. Med Chem. Lett. 2003, 13, 597.
8. Contreras, J. M. Rival, Y.; Chayer, S.; Bourguignon J. J.; Wermuth, C. G. J. Med. Chem. 1999, 42, 730.
9. Betti, L.; Botta, M.; Corelli, F.; Floridi, M.; Fossa, P.; Giannaccini, G.; Manetti, F.; Strappaghetti, G.; Corsano, S. Bioorg. Med. Chem. Lett. 2002, 12, 437.
10. Chand N.; Pillar J.; Diamantis W.; Perhach J. L. Jr.; Sofia, R. D. Eur. J. Pharmacol. 1983, 96, 227.
11. Rival, Y.; Hoffmann, R.; Didier, B.; Rybaltchenki, V.; Bourguignon, J. J.; Wermuth, C. G. J. Med. Chem. 1998, 41, 311.
12. Bongartz, J.P.; Stokbroekx, R.; Van der Aa, M.; Luyckx, M.; Willems, M.; Ceusters, M.; Meerpoel, L.; Smets, G.; Jansen, T.; Wouters, W.; Bowden, C.; Valletta, L.; Herb, M.; Tominovich, R.; Tuman, R. Bioorg. Med. Chem. Lett. 2002, 12 1133.
13. Wermuth, C. G.; Bourguignon, J. J.; Schlewer, G.; Gies, J. P.; Schoenfelder, A.; Melikian, A.; Bouchet, M. J.; Chantreux, D.; Molimard, J. C. J. Med. Chem. 1987, 30, 239.
14. Schmitt, M.; Bourguignon, J. J.; Barlin, G. B.; Davies, L. P. Aust. J. Chem., 1997, 50, 779.
15. Mouton, J. L.; Schmitt, M.; Collot, V.; Bourguignon, J. J. Tetrahedron Lett. 1996, 37, 1787.
16. Biziere, K.; Bourguignon, J. J.; Chambon, J. P.; Heaulme, M.; Perio, A.; Tebib, S.; Wermuth, C. G. British J. Pharmacology 1987, 90, 183.
17. Parrot, I.; Rival, Y.; Wermuth, C. G. Synthesis 1999, 7, 1163.
18. Guery, S.: Parrot I.; Rival, Y.; Wermuth, C.G. Tetrahedron Lett. 2001, 42, 2115.
19. Maes, B. U. W.; Lemiere, G. L. F.; Dommisse, R.; Augustyns, K.; Haemers, A. Tetrahedron 2000, 56, 1777.
20. Turck, A.; Ple, N.; Mojovic, L.; Quequiner, G. Bull. Soc. Chim. France 1993, 130, 488.
21. Maes, B. U. W.; Kosmrlj, J.; Lemiere, G. L. F. J. Heterocycl. Chem. 2002, 39, 535.
22. Maes, B. U. W.; R'kyek, O.; Kosmrlj, J.; Lemiere, G. L. F.; Esmans, E.; Rozenski, J.; Dommisse, R. A.; Haemers Tetrahedron 2001, 57, 1323.
23. Parrot, I.; Ritter, G.; Wermuth, C. G.; Hibert, M. Synlett 2002, 7, 1123.
24. Goodman, A. J.; Stanforth, S. P.; Tarbit, B. Tetrahedron 1999, 55, 15067.
25. Coad, P.; Coad, R. A.; Clough, S.; Hyepock, J.; Salisbury, R.; Wilkins, C. J. Org. Chem. 1963, 28, 218.
26. Draper, T. L.; Bailey, T. R. J. Org. Chem. 1995, 60, 748.
27. Szilagyi, G.; Kasztreiner, E.; Matyus, P.; Kosary, J.; Czako, K.; Cseh, G.; Huszti, Z.; Tardos, L.; Koss, E.; Jaszlits, L. Eur. J. Med. Chem. 1984, 19, 111.
28. Rohr, M.; Toussaint, D.; Chayer, S.; Mann, A.; Suffert, J.; Wermuth, C. G. Heterocycles 1996, 43, 1459.
29. Jones, R. A.; Whitmore, A. P. Tetrahedron 1998, 54, 9519.
30. Ohkuchi, M.; Kyotani, Y.; Shigyo, H.; Koshi, T.; Ohgiya, T.; Matsuda, T.; Kumai, N.; Yasuoka, K. PCT Int. Appl. 2002, 70 pp. WO 2002004427.
31. Coates, W. J.; McKillop, A. J. Org. Chem. 1990, 55, 5418.
32. Pal, M.; Batchu, V. R.; Khanna, S.; Yeleswarapu, K. R. Tetrahedron 2002, 58, 9933.
33. Hickey, D. M. B.; Leeson, P. D.; Carter, S. D.; Goodyear, M. D.; Jones, S. J.; Lewis, N. J.; Morgan, I. T.; Mullane, M. V.; Tricker, J.Y. J. Chem. Soc., Perkin Trans. 1 1988, 12, 3097.
34. Abbotto, A.; Alanzo, V.; Bradamante, S.; Pagani, G. A. J. Chem. Soc., Perkin Trans. 2 1991, 4, 481.
35. Carver, D. R.; Komin, A. P.; Hubbard, J. S.; Wolfe, J. F. J. Org. Chem. 1981, 46, 294.
36. Wermuth, C. G.; Schlewer, G.; Bourguignon, J. J.; Maghioros, G.; Bouchet, M. J.; Moire, C.; Kan, J. P.; Worms, P.; Biziere, K. J. Med. Chem. 1989, 32, 528.
37. Bourguignon, J. J.; Wermuth, C. G. J. Org. Chem. 1981, 46, 4889.
38. Matyus, P.; Fuji, K.; Tanaka, K. Heterocycles 1993, 36, 1975.
39. Coelho, A.; Sotelo, E.; Novoa, H.; Peeters, O. M.; Blaton, N.; Ravina, E. Tetrahedron Lett. 2004, 60, 12177
40. Sotelo, E.; Coelho,.A.; Ravina, E. Tetrahedron Lett. 2003, 44, 4459.
41. Gagnier, R. P.; Halat, M. J.; Otter, B. A. J. Heterocycl. Chem. 1984, 21, 481.
42. Ma, C.; Cho, S.; Falck, J. R.; Shin, D. Heterocycles 2004, 63, 75.
43. Riedl, Z.; Maes, B. U. W.; Monsieurs, K.; Lemiere, G. L. F.; Matyus, P.; Hajos, G. Tetrahedron 2002, 58, 5645.
44. Gong, Y.; He, W. Heterocycles 2004, 62, 851.
45. R'kyek, O.; Maes, B. U. W.; Jonckers, T. H. M.; Lemiere, G. L. F.; Dommisse, R. A. Tetrahedron 2001, 57, 10009.
46. Maes, B. U. W.; Monsieurs, K.; Loones, K. T. J.; Lemiere, G. L. F.; Dommisse, R.; Matyus, P. Riedl, Z.; Hajos, G. Tetrahedron 2002, 58, 9713.
47. Farina, F.; Martin, M. R.; Martin, M. V. Anales de Quimica 1978, 74, 799.
48. Farina, F.; Martin, M. R.; Martin, M. V. Anales de Quimica 1977, 75, 188.
49. Schoenbeck, R.; Kloimstein, E. Monatsh. Chem. 1968, 99, 15.
50. Deinhammer, W.; Wick, M. Ger. Offen. 1978, 11 pp. DE 2706701.
51. Wagner, U. G.; Kratky, C.; Kappe, T. Monatsh Chem. 1989, 120, 329.
52. Turck, A.; Ple, N.; Mojovic, L.; Queguiner, G. J. Heterocycl. Chem. 1990, 27, 1377.
53. Oumouch, S.; Schmitt, M.; Bourguignon, J. J. submitted to Tetrahedron Lett.
54. Yanai, M.; Kinoshita, T. Yakugaku Zasshi 1965, 85, 344. Chem. Abstr. 1965, 63, 5639d.
55. Wise, D. Jr.; CastleJ, R. N. J. Heterocycl. Chem. 1974, 11, 1001.
56. Klinge, D. E.; Van der Plas, H. C.; Geurtsen, G.; Koudijs, Rec. Trav. Chim. Pays-Bas 1974, 93, 236.
57. Bambury, R. E.; Feeley, D. T.; Lawton, G. C.; Weaver, J. M., Wemple, J. J. Med. Chem. 1984, 27, 1613.
58. Greenwood, J. R.; Capper, H. R.; Allan, R.D.; Johnston, G. A. R. J. Internet Journal of chemistry (electronic pub.) 1998, http://www.ijc.com/articles/1998v1/21/
59. Farina, F.; Martin, M. R.; Martin, M. V. Anales de Quimica 1978, 75, 144.
60. Collins, I; Castro, J. L.; Street, L. J. Tetrahedron Lett. 2000, 41, 781.
61. Turck, A.; Ple, N.; Mojovic, L.; Queguiner, G. J. Heterocycl. Chem. 1990, 27, 1377.
62. Ostrowicz, A.; Baloniak, S.; Makosza, Mi.; Rykowski, A. Tetrahedron Lett. 1992, 33, 4787.
63. Cowden, C. J. Org. Lett. 2003, 5, 4497.
64. Hackler, R. E.; Dreikorn, B. A.; Johnson, G. W.; Varie, D. L. J. Org. Chem. 1988, 53, 5704
65. Sparey, T. J.; Harrisson, T. Tetrahedron Lett. 1998, 39, 5873.
66. Winn, M.; De, B.; Zydowsky, T. M.; Altenbach, R. J.; Basha, F. Z.; Boyd, S. A.; Brune, M. E.; Buckner, S. A.; Crowell, D. J. Med. Chem. 1993, 36, 2676.
67. Krbavcic, AL.; Povse, L. Stanovnik, B. Heterocycles 1983, 20, 2347.
68. Heinisch, G.; Matuszczak, B.; Wilke, J. C. Heterocycles 1997, 45, 2385.
69. Yanai, M.; Takeda, S.; Mitsuoka, T. Chem. Pharm. Bull. 1977, 25, 1708.
70. Yanai, M.; Takeda, S.; Nishikawa,, M. Chem. Pharm. Bull. 1977, 25, 1856.
71. Haider, N.; Heinisch, G.; Moshuber, J. Pharmazie 1992, 47, 679.
72. Oumouch, S.; Araujo-Jr, J. X.; Schmitt, M.; Bourguignon, J. J. submitted to Tetrahedron Lett.
73. Tsai, C. S.; Shen, Ai. Y. Arch. Pharm. 1994, 327, 677
74. Kasnar, B.; Wise, D. S.; Kucera, L.S.; Drach, J. C.; Townsend, L.B. Nucleosides & Nucleotides 1994, 13, 459.
75. Galoyan, G. A.; Agbalyan, S. G.; Esayan, G. T. Armyanskii Khimicheskii Zhurnal 1968, 21, 515.
76. Sotelo, E. Molecular diversity, 2004, 8, 159.
77. Peet, N. P. J Heterocycl. Chem. 1984, 21, 1389.
78. Matsuo, T.; Tsukamoto, Y.; Takagi, T.; Sato, M. Chem. Pharm. Bull. 1982, 30, 832.
79. Kotay N., P.; Simig, G.; Barkoczy, J.; Sztruhar, I. Balazs, L.; Doman, I.; Greff, Z.; Ratkai, Z.; Seres, P.; Karancsi, T. PCT Int. Appl. 1999, 52 pp. WO 9964402.
80. Nagashima, H.; Ukai, K.; Oda, H.; Masaki, Y.; Kaji, K. Chem. Pharm. Bull. 1987, 35, 350.
81. Brown, G. R.; Hollinshead, D. M.; Stokes, E. S. E.; Waterson, D.; Clarke, D. S.; Foubister, A. J.; Glossop, S. C.; McTaggart, F.; Mirrlees, D. J.; Smith, G. J.; Wood, R. J. Med. Chem. 2000, 43, 4964.
82. Sircar, I. J. Haterocycl. Chem. 1983, 20 1473.
83. Badger E. W.; Moos, W. H. J. Heterocycl. Chem. 1986, 23, 1515
84. Issac, Y. A. Zeitschrift fuer Naturforschung, B 1999, 54, 1048
85. Estevez, I.; Ravina, E.; Sotelo, E. J Heterocycl. Chem. 1998, 35, 1421.
86. Sotelo, E.; Coelho, A. Ravina, E. Tetrahedron Lett. 2001, 42, 8633.
87. Coelho, A.; Sotelo, E.; Novoa, H.; Peeters, O. M.; Blaton, N.; Ravina, E. Tetrahedron Lett. 2004, 45, 3459.
88. Sotelo, E.; Ravina, E. Synlett 2002, 2, 223
89. Hamberger, H.; Reinshagen, H.; Schulz, G.; Sigmund, G. Tetrahedron Lett. 1977, 41, 3619
90. Schmitt, B.; Oumouch, S.; Schmitt, M.; Bourguignon, J. J. submitted to Tetrahedron. Lett.
91. Bourotte, M.; Pellegrini, N.; Schmitt, M.; Bourguignon, J. J. Synlett 2003, 10, 1482.
92. Ruggli, P.;Hartmann, C. Helvetica Chimica Acta 1920, 3, 493.
93. Lepretre, A.; Turck, A.; Ple, N.; Knochel, P.; Queguiner, G. Tetrahedron Lett. 1999, 56, 265
94. Kang, Y. J.; Lee, W. S.; Kim, H. K.; Yoon, Y. J.; Shiro, M. J. Heterocyclic. Chem. 2000, 37, 1049.
95. Lee, W.; Yoon, Y. J.; Kim, S. K. J. Heterocycl. Chem. 2000, 37, 1591.
96. Kweon, D. H.; Cho, S. D.; Kim, S. K.; Chung, J.W.; Yoon, Y. J. J. Heterocycl. Chem. 1996, 33, 1915.
97. Chang, K.; Kim, J. J.; Kim, Y. K.; Park, H. Y.; Hyun, B. H.; Shiro, M.; Yoon, Y. J.; Lee, W. S. Heterocycles 2001, 55, 1927.
98. Lee, S. G.; Kweon, D. H.; Yoon, Y. J. J. Heterocycl. Chem. 2001, 38, 1179.
99. Elias, O.; Karolyhazy, L.; Horvath, G.; Harmat, V.; Matyus, P. J. Mol. Struc. (Theochem) 2003, 666-667, 625.
100. Maghioros, G.; Schlewer, G.; Wermuth, C. G.; Lagrange, J.; Lagrange, P. Nouveau Journal de Chimie 1983, 7, 667.
101. Matyus, P. Maes, B. U. W.; Riedl, Z.; Hajos, G.; Lemiere, G. L. F. Synlett 2004, 7, 1123.
102. Chayer, S.; Essassi, E. M.; Bourguignon, J. J. Tetrahedron Lett. 1998, 39, 841.