Synthesis and antiproliferative activity evaluation of imidazole-based indeno[1,2-b]quinoline-9,11-dione derivatives

Archives of Pharmacal Research

Volumn 36, Issue 4, 2013, Pages 436-447

  Sarkarzadeh, Hasti ^a   Miri, Ramin ^b   Firuzi, Omidreza ^b   Amini, Mohsen ^a   Razzaghi Asl, Nima ^b   Edraki, Najmeh ^a,b   Shafiee, Abbas ^a  

^a TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b SHIRAZ UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Antiproliferative; Indeno 1,2 b quinoline 9, 11 dione; MTT assay; Synthesis

Indexed keywords

10 (1 METHYL 1H IMIDAZOL 5 YL) 7,8 DIHYDRO 5H INDENO[1,2 B]QUINOLINE 9,11(6H,10H) DIONE; 10 (1 METHYL 1H IMIDAZOL 5 YL) 7,8 DIHYDRO 6H INDENO[1,2 B]QUINOLINE 9,11 DIONE; 10 (1 METHYL 2 (METHYLTHIO) 1H IMIDAZOL 5 YL) 5 PHENYL 7,8 DIHYDRO 5H INDENO[1,2 B]QUINOLINE 9,11(6H,10H) DIONE; 10 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 7,8 DIHYDRO 5H INDENO[3,2 B]QUINOLINE 9,11(6H,10H) DIONE; 10 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 7,8 DIHYDRO 6H INDENO[1,2 B]QUINOLINE 9,11 DIONE; 10 (1H IMIDAZOL 2 YL) 5 PHENYL 7,8 DIHYDRO 5H INDENO[1,2 B]QUINOLINE 9,11(6H,10H) DIONE; 10 (1H IMIDAZOL 2 YL) 7,7 DIMETHYL 5 PHENYL 7,8 DIHYDRO 5H INDENO[1,2 B]QUINOLINE 9,11(6H,10H) DIONE; 10 (1H IMIDAZOL 2 YL) 7,7 DIMETHYL 7,8 DIHYDRO 5H INDENO[1,2 B]QUINOLINE 9,11(6H,10H) DIONE; 10 (1H IMIDAZOL 2 YL) 7,7 DIMETHYL 7,8 DIHYDRO 6H INDENO[1,2 B]QUINOLINE 9,11 DIONE; 10 (1H IMIDAZOL 2 YL) 7,8 DIHYDRO 6H INDENO[1,2 B]QUINOLINE 9,11 DIONE; 10 (4,5 DICHLORO 1H IMIDAZOL 2 YL) 7,7 DIMETHYL 5 PHENYL 7,8 DIHYDRO 5H INDENO[1,2 B]QUINOLINE 9,11(6H,10H) DIONE; 10 (4,5 DICHLORO 1H IMIDAZOL 2 YL) 7,7 DIMETHYL 7,8 DIHYDRO 5H INDENO[1,2 B]QUINOLINE 9,11(6H,10H) DIONE; 10 (4,5 DICHLORO 1H IMIDAZOL 2 YL) 7,7 DIMETHYL 7,8 DIHYDRO 6H INDENO[1,2 B]QUINOLINE 9,11 DIONE; 10 (4,5 DICHLORO 1H IMIDAZOL 2 YL) 7,8 DIHYDRO 5H INDENO[1,2 B]QUINOLINE 9,11(6H,10H) DIONE; 10 (4,5 DICHLORO 1H IMIDAZOL 2 YL) 7,8 DIHYDRO 6H INDENO[1,2 B]QUINOLINE 9,11 DIONE; 7,7 DIMETHYL 10 (1 METHYL 1H IMIDAZOL 5 YL) 7,8 DIHYDRO 5H INDENO[1,2 B]QUINOLINE 9,11(6H,10H) DIONE; 7,7 DIMETHYL 10 (1 METHYL 1H IMIDAZOL 5 YL) 7,8 DIHYDRO 6H INDENO[1,2 B]QUINOLINE 9,11 DIONE; 7,7 DIMETHYL 10 (1 METHYL 2 (METHYLTHIO) 1H IMIDAZOL 5YL) 7,8 DIHYDRO 5H INDENO[1,2 B] QUINOLINE 9,11(6H,10H) DIONE; 7,7 DIMETHYL 10 (1 METHYL 2 (METHYLTHIO) 1H IMIDAZOL 5YL) 7,8 DIHYDRO 6H INDENO[1,2 B]QUINOLINE 9,11 DIONE; 7,7 DIMETHYL 10 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 5 PHENYL 7,8 DIHYDRO 5H INDENO[1,2 B]QUINOLINE 9,11(6H,10H) DIONE; 7,7 DIMETHYL 10 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 7,8 DIHYDRO 5H INDENO[1,2 B]QUINOLINE 9,11(6H,10H) DIONE; 7,7 DIMETHYL 10 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 7,8 DIHYDRO 6H INDENO[1,2 B]QUINOLINE 9,11 DIONE; ANTINEOPLASTIC AGENT; CISPLATIN; DOXORUBICIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON; HUMAN; HUMAN CELL; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION;

ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; HELA CELLS; HUMANS; IMIDAZOLES; INHIBITORY CONCENTRATION 50; JURKAT CELLS; MCF-7 CELLS; MOLECULAR STRUCTURE; NEOPLASMS; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84877876064     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-013-0032-7     Document Type: Article

References (37)

1. Abbas, H.A.S., W.A. El Sayed, and N.M. Fathy. 2010. Synthesis and antitumor activity of new dihydropyridine thioglycosides and their corresponding dehydrogenated forms. European Journal of Medicinal Chemistry 45(3): 973-982.
2. Amini, M., L. Navidpour, and A. Shafiee. 2002. Synthesis and antitubercular activity of new N,N-diaryl-4-(4,5-dichloroimidazole-2-yl)-1,4- dihydro-2,6-dimethyl-3,5-pyridinedicarboxamides. Drug Research 52: 21-26.
3. Bazargan, L., S. Fouladdel, A. Shafiee, M. Amini, S.M. Ghaffari, and E. Azizi. 2008. Evaluation of anticancer effects of newly synthesized dihydropyridine derivatives in comparison to verapamil and doxorubicin on T47D parental and resistant cell lines in vitro. Cell Biology and Toxicology 24(2): 165-174.
4. Brana, M.F., M. Cacho, A. Gradillas, B. Pascual-Teresa, and A. Ramos. 2001. Intercalators as anticancer drugs. Current Pharmaceutical Design 7(17): 1745-1780.
5. Davood, A., N. Mansouri, A.R. Dehpour, H. Shafaroudi, E. Alipour, and A. Shafiee. 2006. Design, synthesis, and calcium channel antagonist activity of new 1,4-dihydropyridines containing 4-(5)-chloro-2-ethyl-5-(4)-imidazolyl substituent. Archiv der Pharmazie - Chemistry in Life Sciences 339: 299-304.
6. Engi, H., H. Sakagami, M. Kawase, A. Parecha, D. Manvar, H. Kothari, P. Adlakha, A. Shan, N. Motohashi, I. Ocsovszki, and J. Molnar. 2006. Tumour-specific cytotoxicity and MDR-reversal activity of dihydropyridines. In vivo 20: 637-644.
7. Fassihi, A., H. Sadeghi, A. Zarghi, and A. Shafiee. 2004. Synthesis and evaluation of calcium channel antagonist activity of new 1,4-dihydropyridines containing phenylamineimidazolyl substitute in guinea-pig ileal smooth muscle. Journal of Research in Medical Sciences 1: 5-10.
8. Fedeli, L., M. Colozza, E. Boschetti, I. Sabalich, C. Aristei, R. Guerciolini, A. Del Favero, R. Rossetti, M. Tonato, P. Rambotti, and S. Davis. 1989. Pharmacokinetics of vincristine in cancer patients treated with nifedipine. Cancer 64(9): 1805-1811.
9. Foroughinia, F., K. Javidnia, Z. Amirghofran, A.R. Mehdipour, and R. Mir. 2008. Design and synthesis of new symmetrical derivatives of dihydropyridine containing a pyridyl group on the 3,5-positions and evaluation of their cytotoxic and multidrug resistance reversal activity. Journal of Pharmacy and Pharmacology 60(11): 1481-1489.
10. Hahn, K.A., A.M. Legendre, and H.M. Schuller. 1997. Amputation and dexniguldipine as treatment for canine appendicular osteosarcoma. Journal of Cancer Research and Clinical Oncology 123(1): 34-38.
11. Hantzsch, A. 1882. Ueber die synthese pyridinartiger verbindungen aus acetessigÃther und aldehydammoniak. Liebigs Annalen der Chemie 215(1): 1-82.
12. Hugel, H.M. 2009. Microwave multicomponent synthesis. Molecules 14(12): 4936-4972.
13. Jabbar, S.A., P.R. Twentyman, and J.V. Watson. 1989. The MTT assay underestimates the growth inhibitory effects of interferons. British Journal of Cancer 60(4): 523-528.
14. Jamalian, A., A. Shafiee, B. Hemmateenejad, M. Khoshneviszadeh, R. Miri, A. Madadkar-Sobhani, S.Z. Bathaie, and A.A. Moosavi-Movahedi. 2011. Novel imidazolyl derivatives of 1,8-acridinedione as potential DNA-intercalating agents. Journal of the Iranian Chemical Society 8(4): 1098-1112.
15. Javidnia, A., T. Akbarzadeh, L. Firoozpour, M. Khoobi, A. Shafiee, and A. Foroumadi. 2011. Synthesis of novel 2-(2-methylsulfonyl-1-methyl-1H-imidazol-5- yl)-5-(alkylsulfonyl)-1,3,4-thiadiazoles. Journal of Heterocyclic Chemistry 48(2): 454-457.
16. Javidnia, K., R. Miri, H. Rezai, A. Jafari, A. Azarmehr, and Z. Amirghofran. 2005. Biological activity and aryltetraline lignans of Linum persicum. Pharmaceutical Biology 43(6): 547-550.
17. Kiue, A., T. Sano, K. Suzuki, H. Inada, M. Okumura, J. Kikuchi, S. Sato, K. Kohno, and M. Kuwano. 1990. Activities of newly synthesized dihydropyridines in overcoming of vincristine resistance, calcium antagonism, and inhibition of photoaffinity labeling of P-glycoprotein in rodents. Cancer Research 50(2): 310-317.
18. Kumar, A., R.A. Maurya, S. Sharma, M. Kumar, and G. Bhatia. 2010. Synthesis and biological evaluation of N-aryl-1,4-dihydropyridines as novel antidyslipidemic and antioxidant agents. European Journal of Medicinal Chemistry 45(2): 501-509.
19. Kumar, R.S., A. Idhayadhullaa, A. Jamal Abdul Nassera, and J. Selvin. 2011. Synthesis and anticoagulant activity of a new series of 1,4-dihydropyridine derivatives. European Journal of Medicinal Chemistry 46(2): 804-810.
20. Leon, R., C. de los RI′os, J. Marco-Contelles, M.G. Lo′pez, A.G. GarcI′a, and M. Villarroya. 2008. Synthesis of 6-amino-1,4- dihydropyridines that prevent calcium overload and neuronal death. European Journal of Medicinal Chemistry 43(3): 668-674.
21. Miri, R., O. Firuzi, P. Peymani, Z. Nazarian, and A. Shafiee. 2011. Synthesis and cytotoxicity study of new cyclopenta [b]quinoline-1,8-dione derivatives. Iranian Journal of Pharmaceutical Research 10(3): 489-496.
22. Miri, R., O. Firuzi, P. Peymani, M. Zamani, A.R. Mehdipour, Z. Heydari, M. Masteri Farahani, and A. Shafiee. 2012. Synthesis, cytotoxicity, and QSAR study of new aza-cyclopenta[b]fluorene-1,9-dione derivatives. Chemical Biology & Drug Design 79(1): 68-75.
23. Miri, R., K. Javidnia, B. Hemmateenejad, A. Azarpira, and Z. Amirghofran. 2004. Synthesis, cytotoxicity, QSAR, and intercalation study of new diindenopyridine derivatives. Bioorganic & Medicinal Chemistry 12(10): 2529-2536.
24. Miri, R., K. Javidnia, H. Mirkhani, F. Kazemi, B. Hemmateenejad, N. Edraki, and A.R. Mehdipour. 2008. Synthesis and in vitro dual calcium channel antagonist-agonist activity of some 1,4-dihydo-2,6-dimethyl-3-nitro and cyano-4-(1-methyl-5-nitro-1H-imidazol-2-yl)-5 pyridinecarboxylates. DARU 16(4): 263-270.
25. Miri, R., R. Motamedi, M.R. Rezaei, O. Firuzi, A. Javidnia, and A. Shafiee. 2010. Design, synthesis and evaluation of cytotoxicity of novel chromeno[4,3-b]quinoline derivatives. Archiv der Pharmazie 1: 111-118.
26. Nekooeian, A.A., A. Khalili, K. Javidnia, A.R. Mehdipour, and R. Miri. 2010. Antihypertensive effects of some new nitroxyalkyl 1,4-dihydropyridine derivatives in rat model of two-kidney, one-clip hypertension. Iranian Journal of Pharmaceutical Research 8(3): 193-199.
27. Ryabokon, N.I., R.I. Goncharova, G. Duburs, and J. Rzeszowska-Wolny. 2005. A 1,4-dihydropyridine derivative reduces DNA damage and stimulates DNA repair in human cells in vitro. Mutation Research - Genetic Toxicology and Environmental Mutagenesis 587(1-2): 52-58.
28. Saini, A., S. Kumar, and J.S. Sandhu. 2008. Hantzsch reaction: Recent advances in Hantzsch 1,4-dihydropyridines. Journal of Scientific and Industrial Research 67(2): 95-111.
29. Shafiee, A., N. Rastkary, M. Jorjani, and B. Shafaghi. 2002. Synthesis and antihypertensive activities of new 1,4-dihydropyridine containing nitroimidazolyl substituent with a nitrooxy group at the 3-ester position. Archiv der Pharmazie 2: 69-76.
30. Shafii, B., M. Amini, T. Akbarzadeh, and A. Shafiee. 2008. Synthesis and antitubercular activity of N3, N5-diaryl-4-(5-arylisoxazol-3-yl)-1,4- dihydropyridine 3,5-dicarboxamide. Journal of Sciences Islamic Republic of Iran 19(4): 323-328.
31. Sirisha, K., G. Achaiah, and V.M. Reddy. 2010. Facile synthesis and antibacterial, antitubercular, and anticancer activities of novel 1,4-dihydropyridines. Archiv der Pharmazie - Chemistry in Life Sciences 343: 342-352.
32. Swarnalatha, G., G. Prasanthi, N. Sirisha, and C. Madhusudhana Chetty. 2011. 1,4-Dihydropyridines: A multtifunctional molecule - A review. International Journal of ChemTech Research 3(1): 75-89.
33. Tallarida, R.J., and R.B. Murray. 1987. Manual of pharmacologic calculations with computer programs. New York: Springer.
34. Tasaka, S., H. Ohmori, N. Gomi, M. Iino, T. Machida, A. Kiue, S. Naito, and M. Kuwano. 2001. Synthesis and structure-activity analysis of novel dihydropyridine derivatives to overcome multidrug resistance. Bioorganic & Medicinal Chemistry Letters 11(2): 275-277.
35. Tolomeo, M., R.A. Gancitano, M. Musso, F. Porretto, R. Perricone, V. Abbadessa, and A. Cajozzo. 1994. Effects of R-enantiomer (GR66234A) and l-enantiomer (GR66235A) of telupidine, a new dihydropyridine derivative, on cell lines displaying the multidrug resistant phenotype. Haematologica 79(4): 328-333.
36. Vanden Eynde, J.J., and A. Mayence. 2003. Synthesis and aromatization of Hantzsch 1,4-dihydropyridines under microwave irradiation: An overview. Molecules 8(4): 381-391.
37. Zhu, L.J., C.L. Zhuang, N. Lei, C.Q. Sheng, W. Guo, Z.Y. Miao, W.F. Liu, J.Z. Yao, and W.N. Zhang. 2011. Synthesis and pharmacological evaluation of novel homocamptothecin-dihydropyridine derivative conjugates as potent topoisomerase I inhibitors. Australian Journal of Chemistry 64(10): 1390-1396.