Synthesis and evaluation of a series of novel imidazolidinone analogues of 6-aminoflavone as anticancer and anti-inflammatory agents

Medicinal Chemistry Research

Volumn 22, Issue 10, 2013, Pages 5066-5075

  Moorkoth, Sudheer ^a   Srinivasan, K K ^a   Gopalan Kutty, N ^a   Joseph, Alex ^a   Naseer, M ^a  

^a MANIPAL COLLEGE OF PHARMACEUTICAL SCIENCES   (India)

Author keywords

6 Aminoflavone; Anti inflammatory; Carrageenan; Cytotoxicity; Ehrlich's ascites; Imidazolidinone

Indexed keywords

2 IMIDAZOLIDINONE DERIVATIVE; 4 (3,4 DICHLOROBENZYLIDENE) 1 (4 OXO 2 PHENYL 4H CHROMEN 6 YL) 2 PHENYL 1H IMIDAZOL 5 ONE; 4 (3,4 DIMETHOXYBENZYLIDENE) 1 (4 OXO 2 PHENYL 4H CHROMEN 6 YL) 2 PHENYL 1H IMIDAZOL 5 ONE; 4 (4 HYDROXYBENZYLIDENE) 1 (4 OXO 2 PHENYL 4H CHROMEN 6 YL) 2 PHENYL 1H IMIDAZOL 5 ONE; 4 (4 METHOXYBENZYLIDENE) 1 (4 OXO 2 PHENYL 4H CHROMEN 6 YL) 2 PHENYL 1H IMIDAZOL 5 ONE; 4 BENZYLIDENE 1 (4 OXO 2 PHENYL 4H CHROMEN 6 YL) 2 PHENYL 1H IMIDAZOL 5 ONE; 6 AMINOFLAVONE; ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC AGENT; CARRAGEENAN; DNA; DOXORUBICIN; FLAVONE DERIVATIVE; HETEROCYCLIC COMPOUND; IMIDAZOLE; PARACETAMOL; SCAFFOLD PROTEIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; ASCITES TUMOR; CANCER RESEARCH; CELL CYCLE PHASE; CONTROLLED STUDY; DNA FRAGMENTATION; DRUG CYTOTOXICITY; DRUG SCREENING; HELA CELL; HUMAN; HUMAN CELL; HYPOTHESIS; IC 50; IN VITRO STUDY; IN VIVO STUDY; LIFESPAN; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

EID: 84883453603     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0486-7     Document Type: Article

References (31)

1. Akama T, Ishida H, Shida Y, Kimura U, Gomi K, Saito H, Fuse E, Kobayashi S, Yoda N, Kasai M (1997) Design and synthesis of potent antitumor 5,4′-diaminoflavone derivatives based on metabolic considerations. J Med Chem 40(12):1894-1900
2. Al-Madi SH, Al-Obaid AM, EI-Subbagh HI (2001) The in vitro antitumor assay of 5-(Z)-arylidene-4-imidazolidinones in screens of AIDS-related leukemia and lymphomas. Anticancer Drugs 12(10):835-839
3. Brian SF, Antony JH, Smith Peter WG, Austin RT (1989) Vogel's Textbook of practical organic chemistry. Longman Scientific & Technical, England
4. 2 histocompatibility antigens in Ehrlich ascites tumour cells. Nature 225(5234):734-735
5. Chern JH, Shia KS, Chang CM, Lee CC, Lee YC, Tai CL, Lin YT, Chang CS, Tseng HY (2004) Synthesis and in vitro cytotoxicity of 5-substituted 2-cyanoimino-4-imidazodinone and 2-cyanoimino-4-pyrimidinone derivatives. Bioorg Med Chem Lett 14(5):1169-1172
6. Cushman M, Zhu H, Geahlen RL, Kraker AJ (1994) Synthesis and biochemical evaluation of a series of aminoflavones as potential inhibitors of protein-tyrosine kinases p56lck, EGFr, and p60v-src. J Med Chem 37(20):3353-3362
7. Denizot F, Lang R (1986) Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J Immunol Methods 89(2):271-277
8. Devi PU, Rao BS, Solomon FE (1998) Effect of plumbagin on the radiation induced cytogenetic and cell cycle changes in mouse Ehrlich ascites carcinoma in vivo. Indian J Exp Biol 36(9):891-895
9. Duvall E, Wyllie AH (1986) Death and the cell. Immunol Today 7(4):115-119
10. Ferte J, Kuhnel JM, Chapuis G, Rolland Y, Lewin G, Schwaller MA (1999) Flavonoid-related modulators of multidrug resistance: synthesis, pharmacological activity, and structure-activity relationships. J Med Chem 42(3):478-489
11. Fotsis T, Pepper MS, Aktas E, Breit S, Rasku S, Adlercreutz H, Wahala K, Montesano R, Schweigerer L (1997) Flavonoids, dietary-derived inhibitors of cell proliferation and in vitro angiogenesis. Cancer Res 57(14):2916-2921
12. Ghosh MN (1984) Toxicity studies: fundamentals of Experimental Pharmacology. Scientific Book Agency, Calcutta
13. Hu YW, Liu CY, Du CM, Zhang J, Wu WQ, Gu ZL (2009) Induction of apoptosis in human hepatocarcinoma SMMC-7721 cells in vitro by flavonoids from Astragalus complanatus. J Ethnopharmacol 123(2):293-301
14. Jung SH, Lee HS, Song JS, Kim HM, Han SB, Lee CW, Lee M, Choi DR, Lee JA, Chung YH, Yoon SJ, Moon EY, Hwang HS, Seong SK, Lee DK (1998) Synthesis and antitumor activity of 4-phenyl-1-arylsulfonyl imidazolidinones. Bioorg Med Chem Lett 8(12):1547-1550
15. Jung SH, Park KL, Lee HS, Whang JS (2001) Evaluation of the role of imidazolidinone motif of antineoplastic 4-phenyl-1-arylsulfonylimidazolidinones using 4-phenyl-2-arylsulfonyloxazolines. Arch Pharm Res 24(6):499-502
16. Khaksari M, Mahani SE, Mahmoodi M (2004) Calcium chanel blockers reduce inflammatory edema in the rat. Indian J Pharmacol 36(6):351-354
17. Khodair AI, El-subbagh HI, Al-obaid AM (1998) Synthesis, conformational analysis and antitumor testing of 5-(Z)-arylidene-4-imidazolidinone derivatives. Phosphorus Sulfur Silicon Relat Elem 140(1):159-181
18. Kim IW, Jung SH (2002) Recognition of the importance of imidazolidinone motif for cytotoxicity of 4-phenyl-1-arylsulfonylimidazolidinones using thiadiazolidine-1,1-dioxide analogs. Arch Pharm Res 25(4):421-427
19. Kuffel MJ, Schroeder JC, Pobst LJ, Naylor S, Reid JM, Kaufmann SH, Ames MM (2002) Activation of the antitumor agent aminoflavone (NSC 686288) is mediated by induction of tumor cell cytochrome P450 1A1/1A2. Mol Pharmacol 62(1):143-153
20. Loaiza-Perez AI, Kenney S, Boswell J, Hollingshead M, Alley MC, Hose C, Ciolino HP, Yeh GC, Trepel JB, Vistica DT, Sausville EA (2004) Aryl hydrocarbon receptor activation of an antitumor aminoflavone: basis of selective toxicity for MCF-7 breast tumor cells. Mol Cancer Ther 3(6):715-725
21. McLean L, Soto U, Agama K, Francis J, Jimenez R, Pommier Y, Sowers L, Brantley E (2008) Aminoflavone induces oxidative DNA damage and reactive oxidative species-mediated apoptosis in breast cancer cells. Int J Cancer 122(7):1665-1674
22. Meng LH, Kohlhagen G, Liao ZY, Antony S, Sausville E (2005) DNA-protein cross-links and replication-dependent histone H2AX phosphorylation induced by aminoflavone (NSC 686288), a novel anticancer agent active against human breast cancer cells. Cancer Res 65(12):5337-5343
23. Nijveldt RJ, Van Nood E, Van Hoorn DE, Boelens PG, Van Norren K, Van Leeuwen PA (2001) Flavonoids: a review of probable mechanisms of action and potential applications. Am J Clin Nutr 74(4):418-425
24. Nitin NA, Soni PA (2005) Reaction of 2′-hydroxy-5′- acetamidochalcones with dimethyl sulfoxide-iodine, pyridine-mercuric(II) acetate and triethanolamine. Indian J Chem 44B:2601-2603
25. Ren W, Qiao Z, Wang H, Zhu L, Zhang L (2003) Flavonoids: promising anticancer agents. Med Res Rev 23(4):519-534
26. Scambia G, Ranelletti FO, Benedetti P, Panici R, Vincenzo G, Bonanno G, Ferrandina, Piantelli MS, Bussa CR, Cianfriglia M (1994) Quercetin potentiates the effect of adriamycin in a multidrug-resistant MCF-7 human breast-cancer cell line: p-glycoprotein as a possible target. Cancer Chemother Pharmacol 34(6):459-464
27. Skehan P, Storeng R, Scudiero D, Monks A, Mc Mohan J, Vistica D, Warren JT, Bokesch H, Kenny S, Boyd MR (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 82(13):1107-1112
28. Stefani ED, Boffetta P, Deneo-Pellegrini H, Mendilaharsu M, Carzoglio JC, Ronco A, Olivera L (1999) Dietary antioxidants and lung cancer risk: a case-control study in Uruguay. Nutr Cancer 34(1):100-110
29. Telford WG, King LE, Fraker PJ (1991) Evaluation of glucocorticoid- induced DNA fragmentation in mouse thymocytes by flow cytometry. Cell Prolif 24(5):447-459
30. Telford WG, King LE, Fraker PJ (1992) Comparative evaluation of several DNA binding dyes in the detection of apoptosis-associated chromatin degradation by flow cytometry. Cytometry 13(2):137-143
31. Winter CA, Risley EA, Nuss GW (1962) Carrageenan induced edema in hind paw of rat as an assay for anti-inflammatory drugs. Proc Soc Exp Biol Med 111:544-547