Design, synthesis and evaluation of cytotoxicity of novel chromeno[4,3-b]quinoline derivatives

Archiv der Pharmazie

Volumn 344, Issue 2, 2011, Pages 111-118

  Miri, Ramin ^a   Motamedi, Radineh ^b   Rezaei, Mohammad Reza ^b   Firuzi, Omidreza ^a   Javidnia, Azita ^c   Shafiee, Abbas ^c  

^a SHIRAZ UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b PAYAME NOOR UNIVERSITY   (Iran)

^c TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

1,4 Dihydropyridines; 4 Hydroxycoumarins; Calcium channel antagonist activity; Cytotoxicity

Indexed keywords

7 (2 CHLOROPHENYL) 8,9,10,12 TETRAHYDRO 7H CHROMENO[4,3 B]QUINOLINE 6,8 DIONE; 7 (2 METHOXYPHENYL) 8,9,10,12 TETRAHYDRO 7H CHROMENO[4,3 B]QUINOLINE 6,8 DIONE; 7 (2 METHYLPHENYL) 8,9,10,12 TETRAHYDRO 7H CHROMENO[4,3 B]QUINOLINE 6,8 DIONE; 7 (2 NITROPHENYL) 8,9,10,12 TETRAHYDRO 7H CHROMENO[4,3 B]QUINOLINE 6,8 DIONE; 7 (3 BROMOPHENYL) 8,9,10,12 TETRAHYDRO 7H CHROMENO[4,3 B]QUINOLINE 6,8 DIONE; 7 (3 CHLOROPHENYL) 8,9,10,12 TETRAHYDRO 7H CHROMENO[4,3 B]QUINOLINE 6,8 DIONE; 7 (3 METHOXYPHENYL) 8,9,10,12 TETRAHYDRO 7H CHROMENO[4,3 B]QUINOLINE 6,8 DIONE; 7 (3 METHYLPHENYL) 8,9,10,12 TETRAHYDRO 7H CHROMENO[4,3 B]QUINOLINE 6,8 DIONE; 7 (4 BROMOPHENYL) 8,9,10,12 TETRAHYDRO 7H CHROMENO[4,3 B]QUINOLINE 6,8 DIONE; 7 (4 CHLOROPHENYL) 8,9,10,12 TETRAHYDRO 7H CHROMENO[4,3 B]QUINOLINE 6,8 DIONE; 7 (4 METHOXYPHENYL) 8,9,10,12 TETRAHYDRO 7H CHROMENO[4,3 B]QUINOLINE 6,8 DIONE; 7 (4 METHYLPHENYL) 8,9,10,12 TETRAHYDRO 7H CHROMENO[4,3 B]QUINOLINE 6,8 DIONE; 7 (4 NITROPHENYL) 8,9,10,12 TETRAHYDRO 7H CHROMENO[4,3 B]QUINOLINE 6,8-DIONE; ANTINEOPLASTIC AGENT; NIFEDIPINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL STRAIN K 562; CELL STRAIN LS 180; CELL STRAIN MCF 7; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; HELA CELL; HUMAN; HUMAN CELL; IC 50; PRIORITY JOURNAL;

ANIMALS; ANTINEOPLASTIC AGENTS; CALCIUM CHANNEL BLOCKERS; CELL LINE, TUMOR; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; GUINEA PIGS; HUMANS; MALE; MOLECULAR STRUCTURE; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79551714931     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.201000196     Document Type: Article

References (40)

1. D. J. Triggle, Mini Rev. Med. Chem. 2003, 3, 215-223.
2. A. M. Katz, N. M. Leach, J. Clin. Pharmacol. 1987, 27, 825-834.
3. A. Davood, N. Mansouri, A. R. Dehpour, H. Shafaroudi, et al., Arch. Pharm. Chem. Life Sci. 2006, 339, 299-304.
4. A. Shafiee, N. Rastkary, M. Jorjani, B. Shafaghi, Arch. Pharm. 2002, 2, 69-76.
5. A. Shafiee, N. Rastkary, M. Jorjani, Arzneim. Forsch. Drug Res. 2002, 52, 537-542.
6. M. Amini, A. Golabchifar, A. R. Dehpour, M. Pirali Hamedani, A. Shafiee, Arzneim. Forsch. Drug Res. 2002, 52, 21-26.
7. F. Fusi, S. Saponara, M. Valoti, S. Dragoni, et al., Curr. Drug Targets 2006, 7, 949-959.
8. L. Bazargan, S. Fouladdel, A. Shafiee, M. Amini, et al., Cell Biol. Toxicol. 2008, 24, 165-174.
9. R. Miri, A. R. Mehdipour, Bioorg. Med. Chem. 2008, 16, 8329-8334.
10. K. A. Hahn, A. M. Legendre, H. M. Schuller, J. Cancer Res. Clin. Oncol. 1997, 123, 34-38.
11. S. R. Morshed, K. Hashimoto, Y. Murotani, M. Kawase, et al., Anticancer Res. 2005, 25, 2033-2038.
12. L. Fedeli, M. Colozza, E. Boschetti, I. Sabalich, et al., Cancer 1989, 6, 1805-1811.
13. J. Jiang, J. Yu, X. X. Sun, Q. Q. Rao, L. Z. Gong, Angew. Chem. Int. Ed. 2008, 47, 2458-2462.
14. C. O. Kappe, W. M. F. Fabian, M. A. Semones, Tetrahedron 1997, 53, 2803-2816.
15. D. J. Triggle, Cell Mol. Neurobiol. 2003, 23, 293-303.
16. M. Schramm, G. Thomas, R. Tower, G. Franckowiak, Nature 1983, 303, 535-537.
17. A. Hantsch, Justus Liebigs Ann. Chem. 1982, 215, 1.
18. B. Love, K. M. Snader, J. Org. Chem. 1965, 30, 1914-1916.
19. Y. Watanabe, K. Shiota, T. Hoshiko, S. Ozako, Synthesis 1983, 761.
20. R. Alajarin, J. J. Vaquero, J. L. G. Navio, J. Alvarez-Builla, Synlett. 1992, 297-298.
21. L. Ãhberg, J. Westman, Synlett. 2001, 1296-1298.
22. M. A. Zolfigol, M. Safaiee, Synlett. 2004, 827-828.
23. S. Tu, C. Miao, Y. Gao, F. Fang, et al., Synlett. 2004, 255-258.
24. W. G. Wang, C. B. Miao, Green Chem. 2006, 8, 1080-1085.
25. S. S. Kang, H. J. Kim, C. Jin, Y. S. Lee, Bioorg. Med. Chem. Lett. 2009, 19, 188-191.
26. A. O. Obaseki, W. R. Porter, J. Heterocycl. Chem. 1982, 19, 385-390.
27. A. K. D. Gupta, R. M. Chaterjee, K. R. Das, Indian J. Chem. 1981, 20B, 511-515.
28. M. A. Hermodson, W. M. Barker, K. P. Link, J. Med. Chem. 1971, 14, 167-169.
29. C. R. Su, S. F. Yeh, C. M. Liu, A. G. Damu, et al., Bioorg. Med. Chem. 2009, 17, 6137-6143.
30. S. Stanchev, G. Momekov, F. Jensen, I. Manolov, Eur. J. Med. Chem. 2008, 43, 694-706.
31. E. Azizi, M. H. Abdolmohammadi, Sh. Fouladdel, A. Shafiee, et al., Daru 2009, 17, 181-186.
32. L. Navidpour, H. Shafaroodi, R. Miri, A. R. Dehpour, A. Shafiee, Il Farmaco 2004, 59, 261-269.
33. I. C. Iranov, S. K. Karagiosov, I. Manolov, Arch. Pharm. 1991, 324, 61-62.
34. Y. Jacquot, L. Bermont, H. Giorgi, B. Refouvelet, et al., Eur. J. Med. Chem. 2001, 36, 127-136.
35. Y. Jacquot, A. Cleern, I. Loios, Y. Ma, et al., Biol. Pharm. Bull. 2002, 25, 335-341.
36. K. Tabakovic, I. Tabakovic, N. Ajdini, O. Leci, Synthesis 1987, 1987, 308-310.
37. R. Miri, H. Niknahad, G. Vesal, A. Shafiee, Farmaco 2002, 57, 123-128.
38. A. R. Mehdipour, K. Javidnia, B. Hemmateenejad, Z. Amirghofran, R. Miri, Chem. Biol. Drug Des. 2007, 70, 337-346.
39. A. Shafiee, R. Motamedi, O. Firuzi, S. Meili, et al., Med. Chem. Res. 2010, published online. DOI 10.1007/s00044-010-9340-3
40. S. A. Jabbar, P. R. Twentyman, J. V. Watson, Br. J. Cancer 1989, 60, 523-528.