Microwave supported synthesis of some novel 1,3-Diarylpyrazino[1,2-a] benzimidazole derivatives and investigation of their anticancer activities

European Journal of Medicinal Chemistry

Volumn 46, Issue 1, 2011, Pages 411-416

  Demirayak, Seref ^a   Kayagil, Ismail ^b   Yurttas, Leyla ^c  

^a ISTANBUL MEDIPOL UNIVERSITY   (Turkey)

^b MEHMET AKIF ERSOY UNIVERSITY   (Turkey)

^c ANADOLU UNIVERSITY   (Turkey)

Author keywords

2 Aryloylbenzimidazole; Anticancer activity; Pyrazino 1,2 a benzimidazole

Indexed keywords

1 (2 PHENYL 2 OXOETHYL) 2 (4 CHLOROBENZOYL)BENZIMIDAZOLE; 1 (2 PHENYL 2 OXOETHYL) 2 (4 METHOXYBENZOYL)BENZOYLBENZIMIDAZOLE; 1 (4 CHLOROPHENYL) 3 (4 CHLOROPHENYL)PYRAZINO[1,2 A]BENZIMIDAZOLE; 1 (4 CHLOROPHENYL) 3 (4 FLUOROPHENYL)PYRAZINO[1,2 A]BENZIMIDAZOLE; 1 (4 CHLOROPHENYL) 3 (4 METHOXYPHENYL)PYRAZINO[1,2 A]BENZIMIDAZOLE; 1 (4 CHLOROPHENYL) 3 (4 METHYLPHENYL)PYRAZINO[1,2 A]BENZIMIDAZOLE; 1 (4 CHLOROPHENYL) 3 PHENYLPYRAZINO[1,2 A]BENZIMIDAZOLE; 1 (4 METHOXYPHENYL) 3 (4 CHLOROPHENYL)PYRAZINO[1,2 A]BENZIMIDAZOLE; 1 (4 METHOXYPHENYL) 3 (4 FLUOROPHENYL)PYRAZINO[1,2 A]BENZIMIDAZOLE; 1 (4 METHOXYPHENYL) 3 (4 METHOXYPHENYL)PYRAZINO[1,2 A]BENZIMIDAZOLE; 1 (4 METHOXYPHENYL) 3 (4 METHYLPHENYL)PYRAZINO[1,2 A]BENZIMIDAZOLE; 1 (4 METHOXYPHENYL) 3 PHENYLPYRAZINO[1,2 A]BENZIMIDAZOLE; 1 [2 (4 CHLOROPHENYL) 2 OXOETHYL] 2 (4 CHLOROBENZOYL)BENZIMIDAZOLE; 1 [2 (4 CHLOROPHENYL) 2 OXOETHYL] 2 (4 METHOXYBENZOYL)BENZOYLBENZIMIDAZOLE; 1 [2 (4 FLUOROPHENYL) 2 OXOETHYL] 2 (4 CHLOROBENZOYL)BENZIMIDAZOLE; 1 [2 (4 FLUOROPHENYL) 2 OXOETHYL] 2 (4 METHOXYBENZOYL)BENZOYLBENZIMIDAZOLE; 1 [2 (4 FLUOROPHENYL) 2 OXOETHYL] 2 BENZOYLBENZIMIDAZOLE; 1 [2 (4 METHOXYPHENYL) 2 OXOETHYL] 2 (4 CHLOROBENZOYL)BENZIMIDAZOLE; 1 [2 (4 METHOXYPHENYL) 2 OXOETHYL] 2 (4 METHOXYBENZOYL)BENZOYLBENZIMIDAZOLE; 1 [2 (4 METHOXYPHENYL) 2 OXOETHYL] 2 BENZOYLBENZIMIDAZOLE; 1 [2 (4 METHYLPHENYL) 2 OXOETHYL] 2 (4 CHLOROBENZOYL)BENZIMIDAZOLE; 1 [2 (4 METHYLPHENYL) 2 OXOETHYL] 2 (4 METHOXYBENZOYL)BENZOYLBENZIMIDAZOLE; 1 PHENYL 3 (4 FLUOROPHENYL)PYRAZINO[1,2 A]BENZIMIDAZOLE; 1 PHENYL 3 (4 METHOXYPHENYL)PYRAZINO[1,2 A]BENZIMIDAZOLE; ACETIC ACID; AMMONIUM ACETATE; ANTINEOPLASTIC AGENT; BENZIMIDAZOLE DERIVATIVE; CISPLATIN; MELPHALAN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MICROWAVE RADIATION;

ANTINEOPLASTIC AGENTS; BENZIMIDAZOLES; CELL LINE, TUMOR; HUMANS; MICROWAVES; SPECTRUM ANALYSIS;

EID: 78650515063     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.11.007     Document Type: Article

References (23)

1. S. Demirayak, and I. Kayagil Synthesis of some 6,8-diarylimidazo[1,2-a] pyrazine derivatives by using either reflux or microwave irradiation method and investigation of their anticancer activities J. Heterocycl Chem. 42 2005 319 325
2. S. Demirayak, and K. Güven Synthesis of some pyrido- and pyrazino-benzimidazole derivatives and their antifungal activity Pharmazie 50 1995 527 529
3. S. Demirayak, and U. Abu Mohsen Anticancer and anti-HIV activities of some pyrido/pyrazino-benzimidazole derivatives Acta Pharm. Turc. 40 1998 9 12
4. A.A. Adjei, and J.K. Buolamwini Novel Anticancer Agents, Strategies for Discovery and Clinical Testing 2006 Elsevier Academic Press New York
5. D.J. Brown The pyrazines Chem. Heterocycl. Compd. Suppl. I 2001 1 346 John Wiley & Sons Inc., Canada
6. C.A. Thurieau, L.F. Poitout, M.O. Galcera, T.D. Gordon, B. Morgan, C.P. Moinet, Preparation of Imidazolyl Derivatives as Agonists or Antagonists of Somatostatin Receptors, WO 99 64,401 (2000).
7. M.O. Contour-Galcera, L. Poitout, C. Moinet, B. Morgan, T. Gordon, P. Roubert, and C. Thurieau Synthesis of imidazopyrazines as ligands for the human somatostatin receptor subtype 5 Bioorg. Med. Chem. Lett. 11 2001 741 745
8. C.A. Thurieau, L.F. Poitout, M.O. Galcera, T. Gordon, B.A. Morgan, C.P. Moinet, D. Bigg, Preparation of Imidazolyl Derivatives as Agonists or Antagonists of Somatostatin Receptors, WO 02 10,140 (2002).
9. C. Prevost, H. Coulomb, O. Lavergne, C. Lanco, B.P. Teng, Preparation of Pharmaceutical Compositions Containing Mikanolide, Dihydromikanolide or an Analog there of Combined with Another Anticancer Agent for Therapeutic Use in Cancer Treatment, WO 02 96,348 (2003).
10. T.D. Gordon, B.A. Morgan, Preparation of Amino Acid Heterobicyclic Amide Derivatives as Farnesyl Transferase Inhibitors, WO 97 30,053 (1997).
11. A. Miyake, Y. Yoshimura, Preparation of (Tetrahydroimidazopyrazinyl) Dihydroquinolines as Antibacterial Agents, JP 01,203,383 (1990).
12. W.C. Lumma, W.C. Randall, E.L. Cresson, J.R. Huff, R.D. Hartman, and T.F. Lyon Piperazinylimidazo[1,2-a]pyrazines with selective affinity for in vitro α-adrenergic receptor subtypes J. Med. Chem. 26 1983 357 363
13. E. Muler-Schweinitzer, and J.R. Fozard SCA 40: studies of the relaxant effects on cryopreserved human airway and vascular amooth muscle Br. J. Pharmacol. 120 1997 1241 1248
14. P.A. Bonnet, A. Michel, F. Laurent, C. Sablayrolles, E. Rechencq, J.C. Mani, M. Boucard, and J.P. Chapat Synthesis and antibronchospastic activity of 8-alkoxy- and 8-(alkylamino)imidazo[1,2-a]pyrazines J. Med. Chem. 35 1992 3353 3358
15. E. Naline, Y.Y. Cui, A. Michel, P.A. Bonnet, H. Bakdach, and C. Advenier Effects of SCA40 on human bronchi and on guinea pig main bronchi n vitro. comparison with cromakalim Fundam. Clin. Pharmacol. 10 1996 368 378
16. O. Vitse, F. Laurent, T.M. Pocock, V. Benezech, L. Zanik, K.R.F. Elliott, G. Subra, K. Portet, J. Bompart, J.P. Chapat, R.C. Small, A. Michel, and P.A. Bonnet New imidazo[1,2-a]pyrazine derivatives with bronchodilatory and cyclic nucleotide phosphodiesterase inhibitory activities Bioorg. Med. Chem. 7 1999 1059 1065
17. W.A. Spitzer, F. Victor, G. Don Pollock, and J.S. Hayes Imidazo[1,2-a]pyrimidines and imidazo[1,2-a]pyrazines: the role of nitrogen position in inotropic activity J. Med. Chem. 31 1988 1590 1595
18. S. Demirayak, U.A. Mohsen, and A.C. Karaburun Synthesis and anticancer and anti-HIV testing of some pyrazino[1,2-a]benzimidazole derivatives Eur. J. Med. Chem. 37 2002 255 260
19. S. Demirayak, U.A. Mohsen, and K. Güven A facile synthesis of 2-aryl-4,5-di(2-thienyl)imidazoles under microwave irradiation and their antimicrobial activities Boll. Chim. Farm. 141 2002 443 664
20. R.N. Cawper, and L.H. Davidson α-Bromoacetophenone Org. Syn. Coll. vol. 2 1943 480
21. M.R. Boyd Status of the NCI preclinical antitumor drug discovery screen Princip. Prac. Oncol. 3 1989 1 12
22. A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, M. Gray-Goodrich, H. Campbell, J. Mayo, and M. Boyd Feasibility of a high-Flux anticancer drug screen using a diverse panel of cultured human tumor cell J. Natl. Cancer Inst. 83 1991 757 766
23. M.R. Boyd, and K.D. Paull Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen Drug Dev. Res. 34 1995 91 109