Synthetic studies on isoquinoline derivatives with multidrug resistance (MDR) modulating activity

Heterocycles

Volumn 63, Issue 1, 2004, Pages 75-85

  Ma, Chen ^a   Cho, Su Dong ^b   Falck, J R ^c   Shin, Dong Soo ^b  

^a SHANDONG UNIVERSITY   (China)

^b Changwon National University   (South Korea)

^c UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 OXAZINE DERIVATIVE; 2 (4 FLUOROBENZYL) 9,10 DIMETHOXY 12 METHYL 6,7,11B,12 TETRAHYDROPYRIDAZINO[4',5',5,6][1,4]OXAZINE[3,4 A]ISOQUINOLIN 1(2H) ONE; ACETONITRILE; ISOQUINOLINE DERIVATIVE; POTASSIUM CARBONATE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG ACTIVITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; MULTIDRUG RESISTANCE; TOXICITY;

EID: 0347024177     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-03-9918     Document Type: Article

References (38)

1. J. E. Van Muijlwijk-Koezen, H. Timmerman, R. Link, H. Vander Goot, and A. P. Ijzerman, J. Med. Chem., 1998, 41, 3987; Q. Zeng, Y. Kwok, S. M. Kerwin, V. Mangold, and L. H. Hurley, J. Med. Chem., 1998, 41, 4273.
2. J. E. Van Muijlwijk-Koezen, H. Timmerman, R. Link, H. Vander Goot, and A. P. Ijzerman, J. Med. Chem., 1998, 41, 3987; Q. Zeng, Y. Kwok, S. M. Kerwin, V. Mangold, and L. H. Hurley, J. Med. Chem., 1998, 41, 4273.
3. F. Fogelman and H. F. Grundy, Br. J. Pharmac., 1970, 38,416.
4. C. A. Winter and J. T. Lehman, J. Pharm. Exp. Ther., 1950, 100, 489.
5. E. Hope, F. L. Pyman, F. G. P. Remfry, and R. Robinson, J. Chem. Soc., 1931, 236.
6. R. D. Larsen, R. A. Reamer, E. G. Corley, P. Davis, E. J. Grabowski, P. J. Reider, and I. Shinkai, J. Org. Chem., 1991, 56, 6034; M. Cushman, D. Nagarathnam, D. Gopal, H. M. He, C. M. Lin, and E. Hamel, J. Med. Chem., 1992, 35, 2293; S. Kirschbaum and H. Waldmann, J. Org. Chem., 1998, 63, 4936; L. Carrillo, D. Badia, E. Dominguez, and E. Aankabe, J. Org. Chem., 1999, 64, 1115.
7. R. D. Larsen, R. A. Reamer, E. G. Corley, P. Davis, E. J. Grabowski, P. J. Reider, and I. Shinkai, J. Org. Chem., 1991, 56, 6034; M. Cushman, D. Nagarathnam, D. Gopal, H. M. He, C. M. Lin, and E. Hamel, J. Med. Chem., 1992, 35, 2293; S. Kirschbaum and H. Waldmann, J. Org. Chem., 1998, 63, 4936; L. Carrillo, D. Badia, E. Dominguez, and E. Aankabe, J. Org. Chem., 1999, 64, 1115.
8. R. D. Larsen, R. A. Reamer, E. G. Corley, P. Davis, E. J. Grabowski, P. J. Reider, and I. Shinkai, J. Org. Chem., 1991, 56, 6034; M. Cushman, D. Nagarathnam, D. Gopal, H. M. He, C. M. Lin, and E. Hamel, J. Med. Chem., 1992, 35, 2293; S. Kirschbaum and H. Waldmann, J. Org. Chem., 1998, 63, 4936; L. Carrillo, D. Badia, E. Dominguez, and E. Aankabe, J. Org. Chem., 1999, 64, 1115.
9. R. D. Larsen, R. A. Reamer, E. G. Corley, P. Davis, E. J. Grabowski, P. J. Reider, and I. Shinkai, J. Org. Chem., 1991, 56, 6034; M. Cushman, D. Nagarathnam, D. Gopal, H. M. He, C. M. Lin, and E. Hamel, J. Med. Chem., 1992, 35, 2293; S. Kirschbaum and H. Waldmann, J. Org. Chem., 1998, 63, 4936; L. Carrillo, D. Badia, E. Dominguez, and E. Aankabe, J. Org. Chem., 1999, 64, 1115.
10. A. Pictet and T. Spengler, Bery 1911, 44, 2030; P. D. Bailey and K. M. Morgan, Chem. Commun., 1996, 1479; E. J. Corey, D. Y. Gin, and R. S. Kania, J. Am. Chem. Soc., 1996, 118, 9202; T. Hino and M. Nakagawa, Heterocycles, 1997, 46, 473; A. Czarnocke and Z. Arazby, Heterocycles, 1999, 44, 2871; E. D. Cox, L. K. Hamaker, J. Li, P. Yu, K. M. Czerwinski, L. Deng, D. W. Bennet, and J. M. Cook, J. Org. Chem., 1997, 62, 44; R. R. Cesati and J. A. Katzenellenbogen, Org. Lett., 2000, 2, 3635.
11. A. Pictet and T. Spengler, Bery 1911, 44, 2030; P. D. Bailey and K. M. Morgan, Chem. Commun., 1996, 1479; E. J. Corey, D. Y. Gin, and R. S. Kania, J. Am. Chem. Soc., 1996, 118, 9202; T. Hino and M. Nakagawa, Heterocycles, 1997, 46, 473; A. Czarnocke and Z. Arazby, Heterocycles, 1999, 44, 2871; E. D. Cox, L. K. Hamaker, J. Li, P. Yu, K. M. Czerwinski, L. Deng, D. W. Bennet, and J. M. Cook, J. Org. Chem., 1997, 62, 44; R. R. Cesati and J. A. Katzenellenbogen, Org. Lett., 2000, 2, 3635.
12. A. Pictet and T. Spengler, Bery 1911, 44, 2030; P. D. Bailey and K. M. Morgan, Chem. Commun., 1996, 1479; E. J. Corey, D. Y. Gin, and R. S. Kania, J. Am. Chem. Soc., 1996, 118, 9202; T. Hino and M. Nakagawa, Heterocycles, 1997, 46, 473; A. Czarnocke and Z. Arazby, Heterocycles, 1999, 44, 2871; E. D. Cox, L. K. Hamaker, J. Li, P. Yu, K. M. Czerwinski, L. Deng, D. W. Bennet, and J. M. Cook, J. Org. Chem., 1997, 62, 44; R. R. Cesati and J. A. Katzenellenbogen, Org. Lett., 2000, 2, 3635.
13. A. Pictet and T. Spengler, Bery 1911, 44, 2030; P. D. Bailey and K. M. Morgan, Chem. Commun., 1996, 1479; E. J. Corey, D. Y. Gin, and R. S. Kania, J. Am. Chem. Soc., 1996, 118, 9202; T. Hino and M. Nakagawa, Heterocycles, 1997, 46, 473; A. Czarnocke and Z. Arazby, Heterocycles, 1999, 44, 2871; E. D. Cox, L. K. Hamaker, J. Li, P. Yu, K. M. Czerwinski, L. Deng, D. W. Bennet, and J. M. Cook, J. Org. Chem., 1997, 62, 44; R. R. Cesati and J. A. Katzenellenbogen, Org. Lett., 2000, 2, 3635.
14. A. Pictet and T. Spengler, Bery 1911, 44, 2030; P. D. Bailey and K. M. Morgan, Chem. Commun., 1996, 1479; E. J. Corey, D. Y. Gin, and R. S. Kania, J. Am. Chem. Soc., 1996, 118, 9202; T. Hino and M. Nakagawa, Heterocycles, 1997, 46, 473; A. Czarnocke and Z. Arazby, Heterocycles, 1999, 44, 2871; E. D. Cox, L. K. Hamaker, J. Li, P. Yu, K. M. Czerwinski, L. Deng, D. W. Bennet, and J. M. Cook, J. Org. Chem., 1997, 62, 44; R. R. Cesati and J. A. Katzenellenbogen, Org. Lett., 2000, 2, 3635.
15. A. Pictet and T. Spengler, Bery 1911, 44, 2030; P. D. Bailey and K. M. Morgan, Chem. Commun., 1996, 1479; E. J. Corey, D. Y. Gin, and R. S. Kania, J. Am. Chem. Soc., 1996, 118, 9202; T. Hino and M. Nakagawa, Heterocycles, 1997, 46, 473; A. Czarnocke and Z. Arazby, Heterocycles, 1999, 44, 2871; E. D. Cox, L. K. Hamaker, J. Li, P. Yu, K. M. Czerwinski, L. Deng, D. W. Bennet, and J. M. Cook, J. Org. Chem., 1997, 62, 44; R. R. Cesati and J. A. Katzenellenbogen, Org. Lett., 2000, 2, 3635.
16. A. Pictet and T. Spengler, Bery 1911, 44, 2030; P. D. Bailey and K. M. Morgan, Chem. Commun., 1996, 1479; E. J. Corey, D. Y. Gin, and R. S. Kania, J. Am. Chem. Soc., 1996, 118, 9202; T. Hino and M. Nakagawa, Heterocycles, 1997, 46, 473; A. Czarnocke and Z. Arazby, Heterocycles, 1999, 44, 2871; E. D. Cox, L. K. Hamaker, J. Li, P. Yu, K. M. Czerwinski, L. Deng, D. W. Bennet, and J. M. Cook, J. Org. Chem., 1997, 62, 44; R. R. Cesati and J. A. Katzenellenbogen, Org. Lett., 2000, 2, 3635.
17. A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 2001, 57, 8297; Z. Czarnocki, D. B. Maclean, and W. Szarek, Heterocycles, 1992, 34, 943; M. Kitamura, Y. Hsiao, M. Ohta, M. Tsukamoto, T. Ohta, H. Takaya, and R. Noyori, J. Org. Chem., 1994, 59, 297.
18. A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 2001, 57, 8297; Z. Czarnocki, D. B. Maclean, and W. Szarek, Heterocycles, 1992, 34, 943; M. Kitamura, Y. Hsiao, M. Ohta, M. Tsukamoto, T. Ohta, H. Takaya, and R. Noyori, J. Org. Chem., 1994, 59, 297.
19. A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 2001, 57, 8297; Z. Czarnocki, D. B. Maclean, and W. Szarek, Heterocycles, 1992, 34, 943; M. Kitamura, Y. Hsiao, M. Ohta, M. Tsukamoto, T. Ohta, H. Takaya, and R. Noyori, J. Org. Chem., 1994, 59, 297.
20. C. B. Ziegler and R. F. Heck, J. Org. Chem., 1978, 46, 4416; R. F. Heck, Org. React., 1982, 27, 345; R. F. Heck, Palladium Reagents in Organic Synthesis; Academic Press: London, 1985; H. Waldmann and S. Kirschbaum, J. Org. Chem., 1998, 63, 4936.
21. C. B. Ziegler and R. F. Heck, J. Org. Chem., 1978, 46, 4416; R. F. Heck, Org. React., 1982, 27, 345; R. F. Heck, Palladium Reagents in Organic Synthesis; Academic Press: London, 1985; H. Waldmann and S. Kirschbaum, J. Org. Chem., 1998, 63, 4936.
22. C. B. Ziegler and R. F. Heck, J. Org. Chem., 1978, 46, 4416; R. F. Heck, Org. React., 1982, 27, 345; R. F. Heck, Palladium Reagents in Organic Synthesis; Academic Press: London, 1985; H. Waldmann and S. Kirschbaum, J. Org. Chem., 1998, 63, 4936.
23. C. B. Ziegler and R. F. Heck, J. Org. Chem., 1978, 46, 4416; R. F. Heck, Org. React., 1982, 27, 345; R. F. Heck, Palladium Reagents in Organic Synthesis; Academic Press: London, 1985; H. Waldmann and S. Kirschbaum, J. Org. Chem., 1998, 63, 4936.
24. W. E. Parham and C. K. Bradsher, Acc. Chem. Res., 1982, 15, 300; M. I. Collado, N. Sotomayor, M. J. Villa, and E. Lete, Tetrahedron Lett., 1996, 37, 6193.
25. W. E. Parham and C. K. Bradsher, Acc. Chem. Res., 1982, 15, 300; M. I. Collado, N. Sotomayor, M. J. Villa, and E. Lete, Tetrahedron Lett., 1996, 37, 6193.
26. M. Schlosser, G. Simig, and H. Geneste, Tetrahedron, 1998, 54, 9023; G. Simig and M. Schlosser, Synlett, 1990, 50; A. Gluszynska and M. D. Rozwadowska, Tetrahedron: Asymmetry, 2000, 11, 2359.
27. M. Schlosser, G. Simig, and H. Geneste, Tetrahedron, 1998, 54, 9023; G. Simig and M. Schlosser, Synlett, 1990, 50; A. Gluszynska and M. D. Rozwadowska, Tetrahedron: Asymmetry, 2000, 11, 2359.
28. M. Schlosser, G. Simig, and H. Geneste, Tetrahedron, 1998, 54, 9023; G. Simig and M. Schlosser, Synlett, 1990, 50; A. Gluszynska and M. D. Rozwadowska, Tetrahedron: Asymmetry, 2000, 11, 2359.
29. I. Coldham, M. L. Middleton, and P. L. Taylor, J. Chem. Soc., Perkin Trans. II, 1997, 2951; A. P. A. Arbore, D. J. Cane-Honeysett, I. Coldham, and M. L. Middleton, Synlett, 2000, 236; T. Shinonara, J. Toda, and T. Sano, Chem. Pharm. Bull., 1997, 45, 813.
30. I. Coldham, M. L. Middleton, and P. L. Taylor, J. Chem. Soc., Perkin Trans. II, 1997, 2951; A. P. A. Arbore, D. J. Cane-Honeysett, I. Coldham, and M. L. Middleton, Synlett, 2000, 236; T. Shinonara, J. Toda, and T. Sano, Chem. Pharm. Bull., 1997, 45, 813.
31. I. Coldham, M. L. Middleton, and P. L. Taylor, J. Chem. Soc., Perkin Trans. II, 1997, 2951; A. P. A. Arbore, D. J. Cane-Honeysett, I. Coldham, and M. L. Middleton, Synlett, 2000, 236; T. Shinonara, J. Toda, and T. Sano, Chem. Pharm. Bull., 1997, 45, 813.
32. G. P. Ellis and G. P. P. West, Eds. Pharmacologically active pyridazines, Elsevier: Amsterdam, 1999, pp. 1-49.
33. W. H. Moos, C. C. Humblet, I. Sircar, C. Rithner, R. E. Weishar, J. A. Bristol, and A. J. Mcphail, J. Med. Chem., 1987, 30, 1963.
34. D. T. Mowry, J. Am. Chem. Soc., 1953, 75, 1909; J. Dury, K. Meier and K. Eichenberger, Helv. Chem. Acta, 1954, 37, 121; T. Kuraishi, Pharm. Bull., 1956, 5, 376.
35. D. T. Mowry, J. Am. Chem. Soc., 1953, 75, 1909; J. Dury, K. Meier and K. Eichenberger, Helv. Chem. Acta, 1954, 37, 121; T. Kuraishi, Pharm. Bull., 1956, 5, 376.
36. D. T. Mowry, J. Am. Chem. Soc., 1953, 75, 1909; J. Dury, K. Meier and K. Eichenberger, Helv. Chem. Acta, 1954, 37, 121; T. Kuraishi, Pharm. Bull., 1956, 5, 376.
37. S. D. Cho, W. Y. Choi, and Y. J. Yoon, J. Heterocycl. Chem., 1996, 33, 1579.
38. R. D. Bryant, F. A. Kunng, and M. S. South, J. Heterocycl. Chem., 1995, 32, 1473.