Microwave-assisted polymer-supported combinatorial synthesis

Current Medicinal Chemistry

Volumn 10, Issue 22, 2003, Pages 2403-2423

  Swamy, K M K ^a   Yeh, Wen Ben ^a   Lin, Mei Jung ^a   Sun, Chung Ming ^a  

^a NATIONAL DONG HWA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID ETHYL ESTER; ACETONE; ACETONITRILE; BENZIMIDAZOLE DERIVATIVE; CARBOLINE DERIVATIVE; CARBON TETRACHLORIDE; COUMARIN DERIVATIVE; HEXANE; MACROGOL; MELATONIN; METHANOL; POLYMER; POLYSTYRENE; PYRIDINE DERIVATIVE; SILDENAFIL; SOLVENT; TETRAHYDROFURAN; TRIAZINE DERIVATIVE; WATER;

CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMBINATORIAL CHEMISTRY; CONTROLLED STUDY; DIELECTRIC CONSTANT; DRUG IDENTIFICATION; DRUG PURIFICATION; DRUG PURITY; DRUG RESEARCH; DRUG SCREENING; DRUG SYNTHESIS; HEATING; LIQUID; METHODOLOGY; MICROWAVE RADIATION; PHARMACOPHORE; PHASE TRANSITION; REACTION TIME; REVIEW; SOLID; STEREOSPECIFICITY; TECHNOLOGY; TEMPERATURE; THEORY; TIME; VELOCITY;

COMBINATORIAL CHEMISTRY TECHNIQUES; HEATING; MICROWAVES; POLYMERS; SOLVENTS;

EID: 0141988603     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929867033456594     Document Type: Review

References (109)

1. Dolle, R. E. J. Comb. Chem. 2000, 2, 383-433.
2. Dolle, R. E. J. Comb. Chem. 2001, 3, 477-517.
3. Dolle, R. E. J. Comb. Chem. 2002, 4, 369-418.
4. Maclean, D.; Baldwin, J. J.; Ivanov, V. T.; Kato, Y.; Shaw, A.; Schineider, P.; Gordon, E. M. J. Comb. Chem. 2000, 2, 562-578.
5. Fenneri, H. Curr. Med. Chem. 1996, 3, 343-378.
6. Cowley, P. M.; Rees, D. C. Curr. Med. Chem. 1997, 4, 211-227.
7. Review see: Sun, C. M. Comb. Chem. High Throughput Screening 1999, 2, 299-509.
8. Sun, C. M. Soluble Polymer-Supported Synthesis of Heterocyclic Libraries. In "Combinatorial Chemistry Methods and Protocols", Methods in Molecular Biology Series; Bellavance, L; Ed.; The Humana Press Inc.: New Jersey, 2002; Chapter 10, 345-371.
9. Bräse, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437.
10. Gedye, R. N.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L.; Laberge, L.; Rousell, J. Tetrahedron Lett. 1986, 27, 279-282.
11. Giguerre, R. T.; Bray, T. L.; Duncan, S. N.; Majetich, G. Tetrahedron Lett. 1986, 28, 4945-4948.
12. Larhed, M.; Hallberg, A. Drug Discovery Today 2001, 6, 406-416.
13. Perriux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223.
14. Lew, A.; Krutzic, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105.
15. Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283.
16. Wathey, B.; Tierney, J.; Lidstrom, P.; Westman, J. Drug Discovery Today 2002, 7, 373-380.
17. Bond, G.; Moyes, R. B.; Pollington, J. D.; Whan, D. A. Chem. Ind. 1991, 686-687.
18. Baghurst, D. R.; Mingos, D. M. P. J. Chem. Soc. Chem. Commun. 1992, 674-677.
19. Metaxas, A. C.; Meridith, R. J. Industrial Microwave Heating. In IEE Power Engineering (Appendix VIII, Series 4).; John, A.T. Eds. pp 335-339, Peregrinus.
20. Pan, P. C.; Sun, C. M. Tetrahedron Lett. 1998, 39, 9505-9508.
21. Shey, J. Y.; Sun, C. M. J. Comb. Chem. 1999, 1, 361-363.
22. Pan, P. C.; Sun, C. M. Tetrahedron Lett. 1999, 40, 6443-6446.
23. Yeh, C, M.; Tung, C, L.; Sun, C. M. J. Comb. Chem. 2000, 2, 341-348.
24. Bendale, P. M.; Sun, C. M. J. Comb. Chem. 2002, 4, 359-361.
25. Yu, H. M.; Chen, S. T.; Chiou, S. H.; Wang, K. T. J. Chromatgr. 1998, 456, 357-362.
26. Yu, H. M.; Chen, S. T.; Wang, K. T. J. Org. Chem. 1992, 57, 4781-4784.
27. Erdélyi, M.; Gogoll, A. Synthesis 2002, 11, 1592-1596.
28. Larhed, M.; Lindebrg, G.; Halberg, A. Tetrahedron Lett. 1996, 37, 8219-8222.
29. Miyayura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
30. Cotterill, I. C.; Usyatinsky, A. Y.; Arnold, J. M.; Clark, D. S.; Dordick, J. S.; Michels, P. C.; Khmelnitsky, Y. L. Tetrahedron Lett. 1998, 39, 1117-1120.
31. Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523-528.
32. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
33. Chandrasekhar, S.; Padmaja, M. B.; Raza, A. Synlett 1999, 10, 1597-1599.
34. Chandrasekhar, S.; Takhi, M.; Reddy, Y. R.; Mahapatra, S.; Rao, C. R.; Reddy, K. V. Tetrahedron 1997, 53, 14997-15004.
35. Keating, T, A.; Armstrong, R. W. J. Org. Chem. 1996, 61, 8935-8939.
36. Hulme, C.; Peng, J.; Tang, S. Y.; Morije, I.; Labaudiniere, R. J. Org. Chem. 1998, 63, 8021-8023.
37. Hulme, C.; Morrisette, M. M.; Volz, F. A.; Burns, C. J. Tetrahedron Lett. 1998, 39, 1113-1116.
38. Harriman, G. C. B. Tetrahedron Lett. 1997, 38, 5591-5594.
39. Gokel, G.; Ludke, G.; Ugi, I. In isonitrile chemistry; Ugi, I., Ed. Academic Press, New York, 1971, pp 145-195.
40. Ugi, I.; Lohberger, S.; Karl, R. The Passerini and Ugi Reactions. In comprehensive Organic Synthesis: Selectivity, strategy and efficiency in modern organic chemistry, Trost, B. M and Heathcock, C. H.; Ed., Pergmon Oxford, 1991.
41. Hoel, A. M. L.; Nielsen, J. Tetrahedron Lett. 1999, 40, 3941-3944.
42. Kim, S. W.; Bauer, S. M.; Armstrong, R. W. Tetrahedron Lett. 1998, 39, 6993-6996.
43. Kuster, G. J.; Scheeren, H. W. Tetrahedron Lett. 2000, 41, 515-519.
44. Dhainaut, A.; Regnier, G.; Tizot, A.; Pierre, A.; Leonce, S.; Guilbaud, N.; Kraus-Berthier, L.; Atassi, G. J. Med. Chem. 1996, 39, 4099-4108.
45. Whitten, J. P.; Xie, Y. F.; Erickson, P. E.; Webb, T. R.; DeSouza, E. B.; Grigoriasdis, D. E.; McCorty, J. R. J. Med. Chem. 1996, 39, 4354-4357.
46. Schaefer, F. C.; Thurston, J. T.; Dudley, J. R. J. Am. Chem. Soc. 1951, 73, 2900-2992.
47. Scharn, D.; Wenschuh, H.; Reineke, U.; Schneider-Mergner, J.; Germeroth, L. J. Comb. Chem. 2000, 2, 361-369.
48. Austin, R. E.; Okonya, J. F.; Bond, D. R. S.; Obeidi, F. A. Tetrahedron Lett. 2002, 43, 6169-6171.
49. Fiorini, M. T.; Abell, C. Tetrahedron Lett. 1998, 39, 1827-1830.
50. Dorff, P. H.; Garigipati, R. S. Tetrahedron Lett. 2001, 42, 2771-2773.
51. Gray, N. S.; Kwon, S.; Schultz, P. G. Tetrahedron Lett. 1997, 38, 1161-1164.
52. Kumar, H. M. S.; Anjaneyulu, S.; Subbareddy, B. V.; Yadav, J. S. Synlett 2000, 1129-1130.
53. Stadler, A.; Kappe, C. O. Tetrahedron 2001, 57, 3915-3920.
54. Strohmeier, G. S.; Kappe, C. O. J. Comb. Chem. 2002, 4, 154-161.
55. Bengston, A.; Halberg, A.; Larhed, M. Org. Lett. 2002, 4, 1231-1233.
56. Reitter, K. Synthesis 1993, 735-762.
57. Mondal, B. C.; Das, A. K. Reactive & Functional Polymers 2002, 53, 45-52.
58. Jao, L. T.; Liang, B. F.; Li, M. H. Tung-hai Hsuch Pao 1983, 24, 489.
59. Dax, S. L.; McNally, J. J.; Youngman, M. A. Curr. Med. Chem. 1999, 6, 255-270.
60. Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043-1052.
61. Kappe, C. O. Acc. Chem. Res. 2000, 33, 879-888.
62. Perez, R.; Beryozkina, T.; Zbruyev, O. I.; Haas, W.; Kappe, C. O. J. Comb. Chem. 2002, 4, 501-510.
63. Finaru, A.; Berthault, A.; Besson, T.; Guillaumet, G.; Raboin, S. B. Org. Lett. 2002, 4, 2613-2615.
64. Ley, S. Y.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
65. Brain, C. T.; Brunton, S. A. Synlett 2001, 382-384.
66. Ley, S. V.; Leach, A. G.; Storer, R. A. J. Chem. Soc., Perkin Trans. 1 2001, 358-361.
67. Gopalakrishnan, G.; Kasinath, V.; Pradeep Singh, N. D. Org. Lett. 2002, 4, 781-782.
68. Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett. 2002, 4, 1567-1570.
69. Baxendale, I. R.; Ley, S. V. Bioorg. Med. Chem. Lett. 2000, 10, 1983-1986.
70. Bestmann, H. J.; Vostrovsky, O. In Topics in Current Chemistry, Wittig Chemistry; Boschke, F. L., Ed.; Springer-Verlag: Berlin, Heidelberg, New York, 1983; Vol. 109, pp 85.
71. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
72. Roth, G. J.; Kirschbaum, S.; Bestmann, H. J. Synlett 1997, 618-620.
73. Kiddle, J. J. Tetrahedron Lett. 2000, 41, 1339-1341.
74. Westman, J. Org. Lett. 2001, 3, 3745-3747.
75. Castells, J.; Font, J.; Virgili, A. J. Chem. Soc. Perkin Trans. 1 1979, 1-5.
76. Söderberg, E.; Westman, J.; Oscarson, S. J. Carbohydr. Chem. 2001, 20, 397-410.
77. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
78. Czarnik, A. W.; DeWitt, S. H. A Practical Guide to Combinatorial Chemistry; American Chemical Society: Washington, D. C. 1997.
79. Fenniri, H. Combinatorial Chemistry; Oxford University Press, Inc: New York. 2000.
80. Seneci, P. Solid-Phase Synthesis and Combinatorial Technologies; John Wileys & Sons, Inc: New York. 2000.
81. Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH Verlag GmbH: Weinheim, 2000.
82. Czarnik, A. W. Solid-Phase Organic Synthesis; John Wileys & Sons: New York. 2001.
83. Gravert, D. J., Janda, K. D. Chem. Rev. 1997, 97, 489-509.
84. For reviews of microwave-assisted reactions in solution phase and solvent free condition: Caddick, S. Tetrahedron 1995, 51, 10403-10432.
85. Galema, S. A. Chem. Soc. Rev. 1997, 26, 233-238.
86. Loupy, A., Petite, A., Hameline, J., Boultet, F. T., Jacqualt, P., Mathe, D. Synthesis 1998, 1213-1234.
87. Varma, R. S. Green Chem. 1999, 1, 43-55.
88. Loupy, A., Perreux, L. Tetrahedron 2001, 57, 9199-9223.
89. Lidström, P.; Tierney, J.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283.
90. Nawrocka, W. Bull. Chim. Farm. 1996, 135, 18-23.
91. Winstanley, P. Lancet 1998, 352, 1080-1081.
92. Carpio, A. J. Neurol. Neurosurg. Psychiatry 1999, 66, 411-412.
93. Navarrete-Vázquez, G.; Cedillo, R.; Hernandez-Campos, A.; Yépez, L.; Hernández-Luis, F.; Valdez, J.; Morales, R.; Cortés, R.; Hernández, M.; Castillo, R. Bioorg. Med. Chem. Lett. 2001, 11, 187-190.
94. Kucukbay, H.; Durmaz, R.; Guven, M.; Gunal, S. Arzneim. Forsch. 2001, 51, 420-424.
95. Zarrinmayeh, A.; Zimmerman, D. M.; Cantrell, B. E.; Schober, D. A.; Bruns, R. B.; Gackenheimer, S. L.; Ornstein, P. L.; Hipskind, P. A.; Brittan, T. C.; Gchiert, D. R. Bioorg. Med. Chem. Lett. 1999, 9, 647-652.
96. Spasov, A. A.; Yozhitsa, I. N.; Bugaeva, L. I.; Anisimova, V. A. Pharm. Chem. J. 1999, 33, 232-243.
97. Preston, P. N. Benzimidazoles and Congeneric Tricyclic Compounds. Part I; Preston, P. N; Ed.; The Chemistry of Heterocyclic Compounds, John Wileys & Sons: New York, 1981; Vol. 1.
98. Solid-pahse synthesis of benzimidazoles: Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1998, 39, 179-182.
99. Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204.
100. Smith, J. M.; Gard, J.; Cummings, W.; Kanizsai, A.; Krchnák, V. J. Comb. Chem. 1999, 1, 368-370.
101. Lee, J.; Coucette, A.; Wilson, N. S.; Lord, J. Tetrahedron Lett. 2001, 42, 2635-2638.
102. Hermkens, P. H. H.; Plate, R.; Kruse, C. G.; Scheeren, H. W.; Ottenheijm, H. C. J. J. Org. Chem. 1992, 57, 3881-3887.
103. Chi, D. Y.; O'Neil, J. P.; Anderson, C. J.; Welch, M. J.; Katzenellenbogen, J. A. J. Med. Chem. 1994, 37, 928-937.
104. Cui, C. B.; Kakeya, H.; Osada, A. Tetrahedron 1997, 53, 59-72.
105. Wu, C. Y.; Sun, C. M. Synlett 2002, 1709-1711.
106. Xia, M.; Wang, Y. G. Tetrahedron Lett. 2002, 43, 7703-7705.
107. Eynde, J. J. V.; Rutot, D. Tetrahedron 1999, 55, 2687-2694.
108. Klein, S. I.; Czekaj, M.; Gardner, C. J.; Guertin, K. R.; Cheney, D. L.; Spada, A. P.; Bolton, S. A.; Brown, K.; Colussi, D.; Heran, C. L.; Morgan, S. R.; Leadley, R. J.; Dunwiddie, C. T.; Perrone, M. H.; Chu, V. J. Med. Chem. 1998, 41, 437-450.
109. Blettner, C. G.; König, W. A.; Stenzel, W.; Schotten, T. J. Org. Chem. 1999, 64, 3885-3890.