Synthesis, evaluation of anticancer activity and COMPARE analysis of N-bis(trifluoromethyl)alkyl-N'-substituted ureas with pharmacophoric moieties

European Journal of Medicinal Chemistry

Volumn 53, Issue , 2012, Pages 364-373

  Luzina, Elena L ^a   Popov, Anatoliy V ^b  

^a INSTITUTE OF PHYSIOLOGICALLY ACTIVE COMPOUNDS   (Russian Federation)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Anticancer activity; COMPARE analysis; Fluorinated ureas; Synthesis

Indexed keywords

1 (1,5 DIMETHYL 3 OXO 2 PHENYL PYRAZOL 4 YL) 3 [2,2,2 TRIFLUORO 1 METHYL 1 (TRIFLUOROMETHYL)ETHYL]UREA; 1 (2,5 DIMETHOXYPHENYL) 3 [2,2,2 TRIFLUORO 1 METHYL 1 (TRIFLUOROMETHYL)ETHYL]UREA; 1 (4 CHLORO 1,3 BENZOTHIAZOL 2 YL) 3 [2,2,2 TRIFLUORO 1 METHYL 1 (TRIFLUOROMETHYL)ETHYL]UREA; 1 (4 METHYL 1,3 BENZOTHIAZOL 2 YL) 3 [2,2,2 TRIFLUORO 1 (TRIFLUOROMETHYL)ETHYL]UREA; 1 (4 METHYL 1,3 BENZOTHIAZOL 2 YL) 3 [2,2,2 TRIFLUORO 1 METHYL 1 (TRIFLUOROMETHYL)ETHYL]UREA; 1 (4,5 DIHYDROTHIAZOL 2 YL) 3 [2,2,2 TRIFLUORO 1 (TRIFLUOROMETHYL)ETHYL]UREA; 1 (4,6 DIMETHYL 1,3 BENZOTHIAZOL 2 YL) 3 [2,2,2 TRIFLUORO 1 (TRIFLUOROMETHYL)ETHYL]UREA; 1 (5 ETHYLSULFANYL 1,3,4 THIADIAZOL 2 YL) 3 [2,2,2 TRIFLUORO 1 (TRIFLUOROMETHYL)ETHYL]UREA; 1 [1,1 BIS(TRIFLUOROMETHYL)PROPYL] 3 (2,5 DIETHOXYPHENYL)UREA; 1 [1,1 BIS(TRIFLUOROMETHYL)PROPYL] 3 (3,4,5 TRIMETHOXYPHENYL) UREA; 1 [1,1 BIS(TRIFLUOROMETHYL)PROPYL] 3 (5 METHYLISOXAZOL 3 YL)UREA; 1 [2 (3,4 DIMETHOXYPHENYL)ETHYL] 3 [2,2,2 TRIFLUORO 1 (TRIFLUOROMETHYL)ETHYL]UREA; 1 [2 (3,4 DIMETHOXYPHENYL)ETHYL] 3 [2,2,2 TRIFLUORO 1 METHYL 1 (TRIFLUOROMETHYL)ETHYL]UREA; 1 [5(TRIFLUOROMETHYL) 1,3,4 THIADIAZOL 2 YL] 3 [2,2,2 TRIFLUORO 1 (TRIFLUOROMETHYL)ETHYL]UREA; ANTINEOPLASTIC AGENT; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA; LUNG NON SMALL CELL CANCER; MELANOMA; NATIONAL HEALTH ORGANIZATION; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CHEMISTRY TECHNIQUES, SYNTHETIC; DRUG SCREENING ASSAYS, ANTITUMOR; ELECTRON TRANSPORT; HUMANS; PATTERN RECOGNITION, AUTOMATED; STRUCTURE-ACTIVITY RELATIONSHIP; UREA;

EID: 84861590223     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.03.026     Document Type: Article

References (68)

1. E.L. Luzina, and A.V. Popov Eur. J. Med. Chem. 44 2009 4944 4953
2. E.L. Luzina, and A.V. Popov Eur. J. Med. Chem. 45 2010 5507 5512
3. C. Barinka, Y. Byun, C.L. Dusich, S.R. Banerjee, Y. Chen, M. Castanares, A.P. Kozikowski, R.C. Mease, M.G. Pomper, and J. Lubkowski J. Med. Chem. 51 2008 7737 7743
4. S.S. Chandran, S.R. Banerjee, R.C. Mease, M.G. Pomper, and S.R. Denmeade Cancer Biol. Ther. 7 2008 974 982
5. Y. Chen, C.A. Foss, Y. Byun, S. Nimmagadda, M. Pullambhatla, J.J. Fox, M. Castanares, S.E. Lupold, J.W. Babich, R.C. Mease, and M.G. Pomper J. Med. Chem. 51 2008 7933 7943
6. M.G. Pomper, J.L. Musachio, J. Zhang, U. Scheffel, Y. Zhou, J. Hilton, A. Maini, R.F. Dannals, D.F. Wong, and A.P. Kozikowski Mol. Imaging 1 2002 96 101
7. J.L. Arias Molecules 13 2008 2340 2369
8. F. Bunz Cancer Biol. Ther. 7 2008 995 996
9. W. Ichikawa Gastric Cancer 9 2006 145 155
10. N. Zhang, Y. Yin, S.-J. Xu, and W.-S. Chen Molecules 13 2008 1551 1569
11. R. Das, and E.F. Plow Cell Cycle 9 2010 638 639
12. A. Koski, M. Raki, P. Nokisalmi, I. Liikanen, L. Kangasniemi, T. Joensuu, A. Kanerva, S. Pesonen, R. Alemany, and A. Hemminki Mol. Ther. 2011
13. F. Wang, D. Zhang, Q. Zhang, Y. Chen, D. Zheng, L. Hao, C. Duan, L. Jia, G. Liu, and Y. Liu Biomaterials 32 2011 9444 9456
14. P. Conti, L. Tamborini, A. Pinto, L. Sola, R. Ettari, C. Mercurio, and M.C. De Eur. J. Med. Chem. 45 2010 4331 4338
15. S.A. Patel, T. Rajale, E. O'Brien, D.J. Burkhart, J.K. Nelson, B. Twamley, A. Blumenfeld, M.I. Szabon-Watola, J.M. Gerdes, R.J. Bridges, and N.R. Natale Bioorg. Med. Chem. 18 2010 202 213
16. J. Matysiak, and A. Opolski Bioorg. Med. Chem. 14 2006 4483 4489
17. K. Akamatsu, M.A. Shibata, Y. Ito, Y. Sohma, H. Azuma, and Y. Otsuki Anticancer Res. 29 2009 2195 2204
18. D.G. McArt, and S.D. Zhang PLoS One 6 2011 e16382
19. M. Yoshida, I. Hayakawa, N. Hayashi, T. Agatsuma, Y. Oda, F. Tanzawa, S. Iwasaki, K. Koyama, H. Furukawa, S. Kurakata, and Y. Sugano Bioorg. Med. Chem. Lett. 15 2005 3328 3332
20. A.M. Al-Obaid, S.G. Abdel-Hamide, H.A. El-Kashef, A.A.M. Abdel-Aziz, A.S. El-Azab, H.A. Al-Khamees, and H.I. El-Subbagh Eur. J. Med. Chem. 44 2009 2379 2391
21. J.S. Fisherman, B.L. Osborn, H.G. Chun, J. Plowman, A.C. Smith, M.C. Christian, D.S. Zaharko, and R.H. Shoemaker Invest. New Drugs 11 1993 1 9
22. H. Turkmen, G. Zengin, and B. Buyukkircali Bioorg. Chem. 39 2011 114 119
23. X.L. Wang, K. Wan, and C.H. Zhou Eur. J. Med. Chem. 45 2010 4631 4639
24. A. Kamal, D. Dastagiri, M. Janaki Ramaiah, J. Surendranadha Reddy, E. Vijaya Bharathi, M. Kashi Reddy, M. Victor Prem Sagar, T. Lakshminarayan Reddy, S.N. Pushpavalli, and M. Pal-Bhadra Eur. J. Med. Chem. 46 2011 5817 5824
25. A.A. Bekhit, and T. Abdel-Aziem Bioorg. Med. Chem. 12 2004 1935 1945
26. N. Benaamane, B. Nedjar-Kolli, Y. Bentarzi, L. Hammal, A. Geronikaki, P. Eleftheriou, and A. Lagunin Bioorg. Med. Chem. 16 2008 3059 3066
27. S.A.M. El-Hawash, E.-S.A.M. Badawey, and I.M. El-Ashmawey Eur. J. Med. Chem. 41 2006 155 165
28. O. Rosati, M. Curini, M.C. Marcotullio, A. Macchiarulo, M. Perfumi, L. Mattioli, F. Rismondo, and G. Cravotto Bioorg. Med. Chem. 15 2007 3463 3473
29. E.G. Vega-Hissi, M.F. Andrada, G.N. Zamarbide, M.R. Estrada, and F. Tomas-Vert J. Mol. Model. 17 2011 1317 1323
30. C. Isanbor, and D. O'Hagan J. Fluorine Chem. 127 2006 303 319
31. K.D. Paull, R.H. Shoemaker, L. Hodes, A. Monks, D.A. Scudiero, L. Rubinstein, J. Plowman, and M.R. Boyd J. Natl. Cancer Inst. 81 1989 1088 1092
32. D.W. Zaharevitz, S.L. Holbeck, C. Bowerman, and P.A. Svetlik J. Mol. Graph Model. 20 2002 297 303
33. Available from: http://dtp.nci.nih.gov/docs/compare/compare.html.
34. A.N. Chekhlov, A.V. Popov, E.L. Luzina, A.N. Pushin, and I.V. Martynov Dokl. Akad. Nauk 339 1994 65 69 [Dokl. Chem. 339(1994) 208-212 (Engl. Transl.)]
35. A.N. Chekhlov, A.V. Popov, and A.N. Pushin Dokl. Akad. Nauk 331 1993 62 65 [Dokl. Chem. 331(1993) 168-172 (Engl. Transl.)]
36. A.V. Popov, A.N. Pushin, and E.L. Luzina Russ. Chem. Bull. 45 1996 482
37. A.V. Popov, A.N. Pushin, and E.L. Luzina Russ. Chem. Bull. 46 1997 1032 1033
38. A.V. Popov, A.N. Pushin, and E.L. Luzina Russ. Chem. Bull. 47 1998 1232 1233
39. A.V. Popov, A.N. Pushin, and E.L. Luzina Russ. Chem. Bull. 49 2000 1202 1206
40. A.V. Popov, A.V. Shastin, E.L. Luzina, A.N. Pushin, and T.N. Gavrishova Russ. Chem. Bull. 48 1999 1548 1552
41. Y.V. Zeifman, E.G. Ter-Gabrielyan, N.P. Gambaryan, and I.L. Knunyants Russ. Chem. Rev. 53 1984 256 273
42. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Adv. Drug Deliv. Rev. 23 1997 3 25
43. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Adv. Drug Deliv. Rev. 46 2001 3 26
44. J.G. Gelovani Small molecules for nuclear diagnosis and therapy: tracers vs drugs 2011 World Molecular Imaging Congress 2011 September San Diego, CA, USA 19 7-10
45. I. Bytheway, M.G. Darley, and P.L. Popelier Chem. Med. Chem. 3 2008 445 453
46. D.E. Clark Future Med. Chem. 3 2011 469 484
47. P. Ertl, B. Rohde, and P. Selzer J. Med. Chem. 43 2000 3714 3717
48. J. Fernandes, and C.R. Gattass J. Med. Chem. 52 2009 1214 1218
49. J. Kelder, P.D. Grootenhuis, D.M. Bayada, L.P. Delbressine, and J.P. Ploemen Pharm. Res. 16 1999 1514 1519
50. J.J. Lu, K. Crimin, J.T. Goodwin, P. Crivori, C. Orrenius, L. Xing, P.J. Tandler, T.J. Vidmar, B.M. Amore, A.G. Wilson, P.F. Stouten, and P.S. Burton J. Med. Chem. 47 2004 6104 6107
51. H. Noorizadeh, A. Farmany, M. Noorizadeh, M. Kohzadi, Drug Test. Anal. 10.1002/dta.288 (2011).
52. T. Noshita, Y. Kidachi, H. Funayama, H. Kiyota, H. Yamaguchi, and K. Ryoyama Eur. J. Med. Chem. 44 2009 4931 4936
53. T. Osterberg, and U. Norinder J. Chem. Inf. Comput. Sci. 40 2000 1408 1411
54. K. Palm, K. Luthman, A.L. Ungell, G. Strandlund, and P. Artursson J. Pharm. Sci. 85 1996 32 39
55. K. Palm, K. Luthman, A.L. Ungell, G. Strandlund, F. Beigi, P. Lundahl, and P. Artursson J. Med. Chem. 41 1998 5382 5392
56. K. Palm, P. Stenberg, K. Luthman, and P. Artursson Pharm. Res. 14 1997 568 571
57. J.M. Campos, R.M. Sanchez-Martin, A. Conejo-Garcia, A. Entrena, M.A. Gallo, and A. Espinosa Curr. Med. Chem. 13 2006 1231 1248
58. P. Eleni, and H.L. Dimitra Mini Rev. Med. Chem. 3 2003 487 499
59. C. Kontogiorgis, and D. Hadjipavlou-Litina Curr. Med. Chem. 17 2010 3162 3214
60. C.A. Kontogiorgis, and D. Hadjipavlou-Litina Med. Res. Rev. 24 2004 687 747
61. E. Pontiki, and D. Hadjipavlou-Litina Med. Res. Rev. 28 2008 39 117
62. H.J. Smith Smith and Williams' Introduction to the Principles of Drug Design and Action 4ed. 2006 CRC Press Boca Raton FL, USA
63. Available from: http://scistore.cambridgesoft.com/ScistoreProductPage. aspx?ItemID=5423.
64. M.C. Alley, D.A. Scudiero, A. Monks, M.L. Hursey, M.J. Czerwinski, D.L. Fine, B.J. Abbott, J.G. Mayo, R.H. Shoemaker, and M.R. Boyd Cancer Res. 48 1988 589 601
65. M.R. Boyd, and K.D. Paull Drug Dev. Res. 34 1995 91 109
66. M.R. Grever, S.A. Schepartz, and B.A. Chabner Semin. Oncol. 19 1992 622 638
67. Available from: http://dtp.cancer.gov/docs/static-pages/compounds/19893. html.
68. T.M. Mawn, A.V. Popov, N.J. Beardsley, K. Stefflova, M. Milkevitch, G. Zheng, and E.J. Delikatny Bioconjug. Chem. 22 2011 2434 2443