Design, synthesis and in vitro antitumor activity of novel N -substituted-4-phenyl/benzylphthalazin-1-ones

European Journal of Medicinal Chemistry

Volumn 89, Issue , 2015, Pages 549-560

  Eldehna, Wagdy M ^a   Ibrahim, Hany S ^a   Abdel Aziz, Hatem A ^b,c   Farrag, Noha N ^d   Youssef, Mohieldin M ^a,d  

^a Egyptian Russian University   (Egypt)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

^c NATIONAL RESEARCH CENTRE   (Egypt)

^d The American University in Cairo   (Egypt)

Author keywords

Antitumor activity; Apoptosis; HepG2; Phthalazin 1 one

Indexed keywords

2 (1 OXO 4 PHENYLPHTHALAZIN 2(1H) YL) N [3 (TRIFLUOROMETHYL)PHENYL]ACETAMIDE; 2 (1 OXO 4 PHENYLPHTHALAZIN 2(1H) YL)N PHENYLACETAMIDE; 2 (4 BENZYL 1 OXOPHTHALAZIN 2(1H) YL) N (2 CHLOROPHENYL)ACETAMIDE; 2 (4 BENZYL 1 OXOPHTHALAZIN 2(1H) YL) N (3 CHLOROPHENYL)ACETAMIDE; 2 (4 BENZYL 1 OXOPHTHALAZIN 2(1H) YL) N (4 FLUOROPHENYL)ACETAMIDE; 2 (4 BENZYL 1 OXOPHTHALAZIN 2(1H) YL) N (4 METHOXYPHENYL)ACETAMIDE; 2 (4 BENZYL 1 OXOPHTHALAZIN 2(1H) YL) N PHENYLACETAMIDE; 2 (4 BENZYL 1 OXOPHTHALAZIN 2(1H) YL) N [3 (TRIFLUOROMETHYL)PHENYL)ACETAMIDE; ANTINEOPLASTIC AGENT; CARBENE; CASPASE 3; DOXORUBICIN; FLUORESCEIN ISOTHIOCYANATE; LIPOCORTIN 5; N (2 CHLOROPHENYL) 2 (1 OXO 4 PHENYLPHTHALAZIN 2(1H) YL)ACETAMIDE; N (3 CHLOROPHENYL) 2 (1 OXO 4 PHENYLPHTHALAZIN 2(1H) YL)ACETAMIDE; N (4 CHLOROPHENYL) 2 (1 OXO 4 PHENYLPHTHALAZIN 2(1H) YL)ACETAMIDE; N (4 FLUOROPHENYL) 2 (1 OXO 4 PHENYLPHTHALAZIN 2(1H) YL)ACETAMIDE; N (4 METHOXYPHENYL) 2 (1 OXO 4 PHENYLPHTHALAZIN 2(1H) YL)ACETAMIDE; PHENYL GROUP; PHTHALAZINE DERIVATIVE; PROTEIN BAX; PROTEIN BCL 2; SORAFENIB; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER CELL LINE; COLON CANCER; CONTROLLED STUDY; CYTOTOXICITY; DOWN REGULATION; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; LIVER CELL CARCINOMA; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE; UPREGULATION; CELL CYCLE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; DRUG SCREENING; HEPG2 CELL LINE; HT 29 CELL LINE; MCF 7 CELL LINE; SYNTHESIS; TUMOR CELL CULTURE;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HEP G2 CELLS; HT29 CELLS; HUMANS; MCF-7 CELLS; MOLECULAR STRUCTURE; PHTHALAZINES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 84908541353     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.10.064     Document Type: Article

References (44)

1. C. Avendano J.C. Menéndez Medicinal Chemistry of Anticancer Drugs First ed. 2008 Elsevier 1 (Chapter 1)
2. K. Nepali S. Sharma M. Sharma P.M.S. Bedi K.L. Dhar Eur. J. Med. Chem. 77 2014 422 487
3. I.H. Hall B.J. Barnes E.S. Ward J.R. Wheaton K.A. Shaffer S.E. Cho A.E. Warren Arch. Pharm. Pharm. Med. Chem. 334 2001 229 234
4. I.H. Hall E.S. Hall O.T. Wong Anti Cancer Drugs 3 1992 55 62
5. I.H. Hall D.W. Covington J.R. Wheaton R.A. Izydore X. Zhou Pharmazie 56 2001 168 174
6. M.C. Cardia S. Distinto E. Maccioni A. Plumitallo L. Sanna M.L. Sanna S. Vigo J. Heterocycl. Chem. 46 2009 674 679
7. S.L. Zhang Y.J. Liu Y.F. Zhao Q.T. Guo P. Gong Chin. Chem. Lett. 21 2010 1071 1074
8. S. Zhang Y. Zhao Y. Liu D. Chen W. Lan Q. Zhao C. Dong L. Xia P. Gong Eur. J. Med. Chem. 45 2010 3504 3510
9. Y. Liu S. Zhang Y. Li J. Wang Y. Song P. Gong Arch. Pharm. Chem. Life Sci. 345 2012 287 293
10. J. Li Y.F. Zhao X.Y. Yuan J.X. Xu P. Gong Molecules 11 2006 574 582
11. X. Zhai J. Li L. He S. Zheng Y.B. Zhang P. Gong Chin. Chem. Lett. 19 2008 29 32
12. K. Miller-Moslin S. Peukert R.K. Jain M.A. McEwan R. Karki L. Llamas N. Yusuff F. He Y. Li Y. Sun M. Dai L. Perez W. Michael T. Sheng H. Lei R. Zhang J. Williams A. Bourret A. Ramamurthy J. Yuan R. Guo M. Matsumoto A. Vattay W. Maniara A. Amaral M. Dorsch J.F. Kelleher J. Med. Chem. 52 2009 3954 3968
13. B.S. Lucas W. Aaron S. An R.J. Austin M. Brown H. Chan A. Chong R. Hungate T. Huang B. Jiang M.G. Johnson J.A. Kaizerman G. Lee D.L. McMinn J. Orf J.P. Powers M. Rong M.M. Toteva C. Uyeda D. Wickramasinghe G. Xu Q. Ye W. Zhong Bioorg. Med. Chem. Lett. 20 2010 3618 3622
14. J.A. Kaizerman W. Aaron S. An R. Austin M. Brown A. Chong T. Huang R. Hungate B. Jiang M.G. Johnson G. Lee B.S. Lucas J. Orf M. Rong M.M. Toteva D. Wickramasinghe G. Xu Q. Ye W. Zhong D.L. McMinn Bioorg. Med. Chem. Lett. 20 2010 4607 4610
15. V.J. Cee, H.L. Deak, B. Du, S.D. Geuns-Meyer, B.L. Hodous, H.N. Nguyen, P.R. Olivieri, V. F. Patel, K. Romero, L. Schenkel, US Patent, 2007, 2007/087276 A1.
16. M. Payton T.L. Bush G. Chung Cancer Res. 70 2010 9846 9854
17. V.J. Cee L.B. Schenkel B.L. Hodous H.L. Deak H.N. Nguyen P.R. Olivieri K. Romero A. Bak X. Be S. Bellon T.L. Bush A.C. Cheng G. Chung S. Coats P.M. Eden K. Hanestad P.L. Gallant Y. Gu X. Huang R.L. Kendall M.J. Lin M.J. Morrison V.F. Patel R. Radinsky P.E. Rose S. Ross J. Sun J. Tang H. Zhao M. Payton S.D. Geuns-Meyer J. Med. Chem. 53 2010 6368 6377
18. G. Bold, J. Frei, P. Traxler, K.-H. Altmann, H. Mett, D.R. Stover, J.M. Wood, EP Patent, 1998, 98/00764.
19. G. Bold K.-H. Altmann J. Frei M. Lang P.W. Manley P. Traxler B. Wietfeld J. Brüggen E. Buchdunger R. Cozens S. Ferrari P. Furet F. Hofmann G. Martiny-Baron J. Mestan J. Rösel M. Sills D. Stover F. Acemoglu E. Boss R. Emmenegger L. Lässer E. Masso R. Roth C. Schlachter W. Vetterli D. Wyss J.M. Wood J. Med. Chem. 43 2000 2310 2323
20. J. Dumas J.A. Dixon Expert Opin. Ther. Pat. 15 2005 647 658
21. E.L. Piatnitski M.A.J. Duncton A.S. Kiselyov R. Katoch-Rouse D. Sherman D.L. Milligan C. Balagtas W.C. Wong J. Kawakamia J.F. Doody Bioorg. Med. Chem. Lett. 15 2005 4696 4698
22. M.A.J. Duncton E.L. Piatnitski R. Katoch-Rouse L.M. Smith A.S. Kiselyov D.L. Milligan C. Balagtas W.C. Wong J. Kawakamia J.F. Doody Bioorg. Med. Chem. Lett. 16 2006 1579 1581
23. A.S. Kiselyov V.V. Semenov D. Milligan Chem. Biol. Drug Des. 68 2006 308 313
24. A.S. Kiselyov M. Semenova V.V. Semenov E.L. Piatnitski Chem. Biol. Drug Des. 68 2006 250 255
25. M.A.J. Duncton E.L.P. Chekler R. Katoch-Rouse D. Sherman W.C. Wong L.M. Smith J.K. Kawakami A.S. Kiselyov D.L. Milligan C. Balagtas Y.R. Hadari Y. Wang S.N. Patel R.L. Rolster J.R. Tonra D. Surguladze S. Mitelman P. Kussie P. Bohlen J.F. Doody Bioorg. Med. Chem. 17 2009 731 740
26. J.C. Tille J. Wood S.J. Mandriota C. Schnell S. Ferrari J. Mestan Z. Zhu L. Witte M.S. Pepper J. Pharm. Exp. Ther. 299 2001 1073 1085
27. G. Papeo E. Casale A. Montagnoli A. Cirla Expert Opin. Ther. Pat. 23 2013 503 514
28. V.M. Loh X.-l. Cockcroft K.J. Dillon L. Dixon J. Drzewiecki P.J. Eversley S. Gomez J. Hoare F. Kerrigan I.T.W. Matthews K.A. Menear N.M.B. Martin R.F. Newton J. Paul G.C.M. Smith J. Vilec A.J. Whittlec Bioorg. Med. Chem. Lett. 15 2005 2235 2238
29. X.L. Cockcroft K.J. Dillon L. Dixon J. Drzewiecki F. Kerrigan V.M. Loh N.M.B. Martin K.A. Menear G.C.M. Smith Bioorg. Med. Chem. Lett. 16 2006 1040 1044
30. K.A. Menear C. Adcock R. Boulter X.-l. Cockcroft L. Copsey A. Cranston K.J. Dillon J. Drzewiecki S. Garman S. Gomez H. Javaid F. Kerrigan C. Knights A. Lau V.M. Loh I.T.W. Matthews S. Moore M.J. O'Connor G.C.M. Smith N.M.B. Martin J. Med. Chem. 51 2008 6581 6591
31. M.E. Prime S.M. Courtney F.A. Brookfield R.W. Marston V. Walker J. Warne A.E. Boyd N.A. Kairies W.v.d. Saal A. Limberg G. Georges R.A. Engh B. Goller P. Rueger M. Rueth J. Med. Chem. 54 2011 312 319
32. P. Skehan R. Storeng D. Scudiero A. Monks J. McMahon D. Vistica J.T. Warren H. Bokesch S. Kenney M.R. Boyd J. Natl. Cancer Inst. 82 1990 1107 1112
33. A. Jemal F. Bray M.M. Center J. Ferlay E. Ward D. Forman CA Cancer. J. Clin. 61 2011 69 90
34. J.F. Perz G.L. Armstrong L.A. Farrington Y.J.F. Hutin B.P. Bell J. Hepatol. 45 2006 529 538
35. J. Massagué Nature 432 2004 298 306
36. Y. Tsujimoto C.M. Croce Proc. Natl. Acad. Sci. U. S. A. 83 1986 5214 5218
37. S. Krajewski C. Blomqvist K. Franssila Cancer Res. 55 1995 4471 4478
38. S. Haldar J. Chintapalli C.M. Croce Cancer Res. 56 1996 1253 1255
39. E. Hernández-Núñez H. Tlahuext R. Moo-Puc H. Torres-Gómez R. Reyes-Martínez R. Cedillo-Rivera C. Nava-Zuazo G. Navarrete-Vazquez Eur. J. Med. Chem. 44 2009 2975 2984
40. I.E. Virsis D.A. Silaraya B.A. Grinberga A.A. Prikulis I.D. Gerbashevska M.E. Orenish Khim. Farm. Zh. 15 1981 23 26
41. Z. Aktürk F. Klc K. Erol V. Pabuçcuolu Il Farm. 57 2002 201 206
42. H.M.B. Cid C. Tränkle K. Baumann R. Pick E. Mies-Klomfass E. Kostenis K. Mohr U. Holzgrabe J. Med. Chem. 43 2000 2155 2164
43. R. Weiss Org. Syn. Coll. 2 1943 61
44. P.A. Procopiou C. Browning J.M. Buckley K.L. Clark L. Fechner P.M. Gore A.P. Hancock S.T. Hodgson D.S. Holmes M. Kranz B.E. Looker K.M.L. Morriss D.L. Parton L.J. Russell R.J. Slack S.L. Sollis S. Vile C.J. Watts J. Med. Chem. 54 2011 2183 2195