Synthesis and antimalarial activity of 7-benzylamino-1-isoquinolinamines

Journal of Heterocyclic Chemistry

Volumn 44, Issue 3, 2007, Pages 633-637

  Gutteridge, Clare E ^a   Hoffman, Marshall M ^a   Bhattacharjee, Apurba K ^b   Gerena, Lucia ^b  

^a UNITED STATES NAVAL ACADEMY   (United States)

^b WALTER REED ARMY INSTITUTE OF RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,7 ISOQUINOLINEDIAMINE; 7 BENZYLAMINO 1 ISOQUINOLINAMINE DERIVATIVE; ANTIMALARIAL AGENT; CHLOROQUINE; ISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ANTIMALARIAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PLASMODIUM FALCIPARUM; REACTION ANALYSIS;

EID: 38949120336     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570440319     Document Type: Article

References (24)

1. Greenwood, B.; Mutabingwa, T. Nature 2002, 415, 670.
2. Chen, M.; Theander, T. G.; Christensen, S. B.; Hviid, L.; Zhai, L.; Kharazmi, A. Antimicrob. Agents Chemother. 1994, 37, 1470.
3. Chen, M.; Christensen, S. B.; Zhai, L.; Rasmussen, R.; Theander, T. G.; Frokjaer, S.; Steffansen, B.; Davidsen, J.; Kharazmi, A. J. of Infectious Diseases 1997, 176, 1327.
4. Li, R.; Kenyon, G. L.; Cohen, F. E.; Chen, X.; Gong, B.; Dominguez, J. N.; Davidson, E.; Kurzban, G.; Miller, R. E.; Nuzum, E. O.; Rosenthal, P. J.; McKerrow, J. H. J. Med. Chem. 1995, 38, 5031.
5. Liu, M.; Wilairat, P.; Go, M.-L. J. Med. Chem. 2001, 44, 4443.
6. Dominguez, J. N.; Charris, J. E.; Lobo, G.; Gamboa de Dominguez, N.; Moreno, M. M.; Riggione, F.; Sanchez, E.; Olsen, J.; Rosenthal, P. J. Eur. J. Med. Chem. 2001, 36, 555.
7. Go, M.-L.; Liu, M.; Wilairat, P.; Rosenthal, P. J.; Saliba, K. J.; Kirk, K. Antimicrob. Agents Chemother. 2004, 48, 3241.
8. Ziegler, H. L.; Hansen, H. S.; Staerk, D.; Christensen, S. B.; Hägerstrand, H.; Jaroszewski, J. W. Antimicrob. Agents Chemother. 2004, 48, 4067.
9. Dominguez, J. N.; Leon, C.; Rodrigues, J.; Gamboa de Dominguez, N.; Gut, J.; Rosenthal, P. J. J. Med. Chem. 2005, 48, 3654.
10. Gutteridge, C. E.; Nichols, D. A.; Curtis, S. M.; Thota, D. S.; Vo, J. V.; Gerena, L.; Montip, G.; Asher, C. O.; Diaz, D. S.; DiTusa, C. A.; Smith, K. S.; Bhattacharjee, A. K. Bioorg. Med. Chem. Lett. 2006, 16, 5682.
11. Bhattacharjee, A. K.; Nichols, D. A.; Gerena, L.; Gutteridge, C. E. Medicinal Chemistry 2007 manuscript in press.
12. Davoll, J.; Johnson, A. M.; Davies, H. J.; Bird, O. D.; Clarke, J.; Elslager, E. F. J. Med. Chem. 1972, 15, 812.
13. Schmidt, L. H. Am. J. Trop. Med. Hyg. 1979, 28, 793.
14. Roth, B.; Cheng, C. C. Prog. Med. Chem. 1982, 19, 269.
15. Ghose, A. K.; Crippen, G. M. J. Med. Chem. 1984, 27, 901.
16. Rydon, H. N.; Undheim, K. J. Chem. Soc. 1962, 4689.
17. Shinkai, H.; Ito, T.; Yamada, H. Worldwide Patent WO9948492, 1999; Chem. Abstr. 1999, 131, 257447.
18. Zhu, B.-Y.; Su, T.; Zhaozhong, J. J.; Scarborough, R. M. Worldwide Patent WO0071507, 2000; Chem. Abstr. 2000, 134, 29203.
19. Gunzenhauser, S.; Balli, H. Helv. Chim. Acta 1989, 72, 1186.
20. Ajao, J. F.; Bird, C. W. J. Heterocycl. Chem. 1985, 22, 329.
21. Grunewald, G. L.; Dahanukar, V. H.; Jalluri, R. K.; Criscione, K. R. J. Med. Chem. 1999, 42, 118.
22. Potter, M. D.; Taylor, E. P. J. Chem. Soc. 1953, 1320.
23. This was seen in a structurally-related series of 2,4- quinazolinediamines, Werbel, L. M.; Elslager, E. F.; Newton, L. S. J. Heterocycl. Chem. 1987, 24, 345.
24. Armarego, W. L. F.; Batterham, T. J. J. Chem. Soc., Section B 1966, 750.