Synthesis, anticancer activity and pharmacokinetic analysis of 1-[(substituted 2-alkoxyquinoxalin-3-yl)aminocarbonyl]-4-(hetero)arylpiperazine derivatives

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 3, 2012, Pages 1303-1309

  Lee, Young Bok ^a   Gong, Young Dae ^b   Kim, Deog Joong ^a   Ahn, Chang Ho ^a   Kong, Jae Yang ^c   Kang, Nam Sook ^d  

^a Rexahn Pharmaceuticals Inc   (United States)

^b Dongguk University   (South Korea)

^c Gyeongsang National University   (South Korea)

^d Chungnam National University   (South Korea)

Author keywords

2 Alkoxyquinoxalin (hetero) arylpiperazine; Anti cancer; Bioavailability; Oral; Pharmacokinetics

Indexed keywords

1 (3,5 DIMETHOXYPHENYL) 4 [(3 METHOXY 5 METHYLQUINOXALIN 2 YL)AMINOCARBONYL] PIPERAZINE; 1 (3,5 DIMETHOXYPHENYL) 4 [(3,5 DIMETHOXYQUINOXALIN 2 YL)AMINOCARBONYL]PIPERAZINE; 1 (3,5 DIMETHOXYPHENYL) 4 [(6 FLUORO 2 METHOXYQUINOXALIN 3 YL)AMINOCARBONYL] PIPERAZINE; 1 (3,5 DIMETHYLPHENYL) 4 [(3 METHOXY 5 METHYLQUINOXALIN 2 YL)AMINOCARBONYL] PIPERAZINE; 1 (3,5 DIMETHYLPHENYL) 4 [(3 METHOXY 6 METHYLQUINOXALIN 2 YL)AMINOCARBONYL] PIPERAZINE; 1 [(3,5 DIMETHOXYQUINOXALIN 2 YL)AMINOCARBONYL] 4 (3,5 DIMETHYLPHENYL)PIPERAZINE; 1 [(3,6 DIMETHOXYQUINOXALIN 2 YL)AMINOCARBONYL] 4 (3,5 DIMETHYLPHENYL)PIPERAZINE; 1 [(6 FLUORO 3 METHOXYQUINOXALIN 2 YL)AMINOCARBONYL] 4 (3,5 DIMETHYLPHENYL)PIPERAZINE; 1 [(SUBSTITUTED 2 ALKOXYQUINOXALIN 3 YL)AMINOCARBONYL] 4 (HETERO)ARYLPIPERAZINE DERIVATIVE; ANTINEOPLASTIC AGENT; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CANCER CELL CULTURE; CELL PROLIFERATION; CONCENTRATION RESPONSE; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG HALF LIFE; DRUG IDENTIFICATION; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; MALE; NONHUMAN; PHARMACOKINETICS; RAT;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MALE; NEOPLASMS; PIPERAZINES; QUINOXALINES; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP;

RATTUS;

EID: 84856235620     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.12.026     Document Type: Article

References (32)

1. M. Kovalenko, A. Gazit, A. Böhmer, C. Rorsman, L. Rönnstrand, C.H. Heldin, J. Waltenberger, F.D. Böhmer, and A. Levitzki Cancer Res. 54 1994 6106
2. A. Levitzki, and A. Gazit Science 267 1995 1782
3. S. Banai, Y. Wolf, G. Golomb, A. Pearle, J. Waltenberger, I. Fishbein, A. Schneider, A. Gazit, L. Perez, R. Huber, G. Lazarovichi, L. Rabinovich, A. Levitzki, and S.D. Gertz Circulation 97 1998 1960
4. M.N. Noolvi, H.M. Patel, V. Bhardwaj, and A. Chauhan Eur. J. Med. Chem. 46 2011 2327
5. H. Gao, E.F. Yamasaki, K.K. Chan, L.L. Shen, and R.M. Snapka Mol. Pharmacol. 63 2003 1382
6. H.U. Gali-Muhtasib, M.J. Haddadin, D.N. Rahhal, and I.H. Younes Oncol. Rep. 8 2001 679
7. M. Diab-Assef, M.J. Haddadin, P. Yared, C. Assaad, and H.U. Gali-Muhtasib Mol. Carcinog. 33 2002 198
8. A. Monge, F.J. Martínez-Crespo, A. López de Ceráin, J.A. Palop, S. Narro, V. Senador, A. Marín, Y. Sainz, M. González, E. Hamilton, and A.J. Barker J. Med. Chem. 38 1995 4488
9. N.C. Kakodkar, R. Peddinti, M. Kletzel, Y. Tian, L.J. Guerrero, S.D. Undevia, D. Geary, A. Chlenski, Q. Yang, H.R. Salwen, and S.L. Cohn Pediatr. Blood Cancer 56 2011 164
10. R.H. Shoemaker Cancer Treat. Rep. 70 1986 9
11. F. Valeriote, T. Corbett, M. Edelstein, and L. Baker Clin. Sci. Rev. 14 1996 124
12. T.H. Corbett, P. LoRusso, L. Demchick, C. Simpson, S. Pugh, K. White, J. Kushner, L. Polin, J. Meyer, J. Czarnecki, L. Heilbrun, J.P. Horwitz, J.L. Gross, C.H. Behrens, B.A. Harrison, R.J. McRipley, and G. Trainor Investig. New Drugs 16 1998 129
13. S. Undevia, F. Innocenti, J. Ramirez, L. House, A.A. Desai, L.A. Skoog, D.A. Singh, T. Karrison, H.L. Kindler, and M.J. Ratain Eur. J. Cancer 44 2008 1684
14. J.R. Rigas, W.P. Tong, M.G. Kris, J.P. Orazem, C.W. Young, and R.P. Warrell Jr. Cancer Res. 52 1992 6619
15. V.A. Miller, J.R. Rigas, W.P. Tong, J.R. Reid, K.M. Pisters, S.C. Grant, R.T. Heelan, and M.G. Kris Cancer Chemother. Pharmacol. 40 1997 415
16. Cho, E.-H.; Chung, S.-G.; Lee, S.-H.; Kwon, H.-S.; Kang, D.-W.; Joo, J.-H.; Lee, Y.-H. U.S. Patent 6,683,184, 2004.
17. E.-Y. Yi, E.-J. Jeong, H.S. Song, M.-S. Lee, D.-W. Kang, J.-H. Joo, H.-S. Kwon, S.-H. Lee, S.-K. Park, S.-G. Chung, E.-H. Cho, and Y.-J. Kim Int. J. Oncol. 25 2004 365
18. Y.B. Lee, Y.D. Gong, H. Yoon, C.-H. Ahn, M.K. Jeon, and J.Y. Kong Biorg. Med. Chem. 18 2010 7966
19. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney, and M.R. Boyd J. Natl. Cancer Inst. 82 1990 1107
20. D.F. Veber, S.R. Jhonson, H.Y. Cheng, B.R. Smith, K.W. Ward, and K.D. Kopple J. Med. Chem. 45 2002 2615
21. T. Takagi, C. Ramachandran, M. Bermejo, S. Yamashita, L.X. Yu, and G.L. Amidon Mol. Pharm. 3 2006 631
22. M.M. Hann, and T.I. Oprea Curr. Opin. Chem. Biol. 8 2004 255
23. J. Chou, and P. Jurs J. Chem. Inf. Comput. Sci. 19 1979 172
24. A. Cheng, and K. Merz Jr. J. Med. Chem. 46 2003 3572
25. J.H. Kim, C.H. Chae, S.M. Kang, J.Y. Lee, G.N. Lee, S.H. Hwang, and N.S. Kang Bull. Kor. Chem. Soc. 32 2011 1237
26. Y. Dong, and S.S. Feng Biomaterials 26 2005 6068
27. D.R. Kalaria, G. Sharma, V. Beniwal, and M.N. Ravi Kumar Pharm Res. 26 2009 492
28. H. Chen, Y. Zheng, G. Tian, Y. Tian, X. Zeng, G. Liu, K. Liu, L. Li, Z. Li, L. Mei, and L. Huang Nanoscale Res. Lett. 6 2011 4
29. D.J. Hauss Adv. Drug Deliv. Rev. 59 2007 667
30. J.L. Arias, B. Clares, M.E. Morales, V. Gallardo, and M.A. Ruiz Curr. Drug Targets 12 2011 1151
31. G. Gaucher, P. Satturwar, M.C. Jones, A. Furtos, and J.C. Leroux Eur. J. Pharm. Biopharm. 76 2010 147
32. M.S. Lam Pharmacotherapy 31 2011 164