Synthesis and structure-activity relationships of N-benzyl-N-(X-2-hydroxybenzyl)-N′-phenylureas and thioureas as antitumor agents

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 1, 2010, Pages 305-313

  Li, Huan Qiu ^a   Yan, Tao ^a   Yang, Ying ^a   Shi, Lei ^a   Zhou, Chang Fang ^a   Zhu, Hai Liang ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

Anticancer agents; EGFR; HER 2; Structure activity relationship; Thiourea; Urea

Indexed keywords

1 (2 HYDROXY 3,5 DIMETHYLBENZYL) 1 (4 HYDROXYBENZYL) 3 PHENYLTHIOUREA; 1 (2 HYDROXY 3,5 DIMETHYLBENZYL) 1 (4 HYDROXYBENZYL) 3 PHENYLUREA; 1 (2 HYDROXY 5 METHYLBENZYL) 1 (4 HYDROXYBENZYL) 3 PHENYLUREA; 1 (3,5 DIBROMO 2 HYDROXYBENZYL) 1 (4 FLUOROBENZYL) 3 PHENYLTHIOUREA; 1 (3,5 DIBROMO 2 HYDROXYBENZYL) 1 (4 FLUOROBENZYL) 3 PHENYLUREA; 1 (3,5 DIBROMO 2 HYDROXYBENZYL) 1 (4 HYDROXYBENZYL) 3 PHENYLTHIOUREA; 1 (3,5 DIBROMO 2 HYDROXYBENZYL) 1 (4 HYDROXYBENZYL) 3 PHENYLUREA; 1 (3,5 DICHLORO 2 HYDROXYBENZYL) 1 (4 FLUOROBENZYL) 3 PHENYLTHIOUREA; 1 (3,5 DICHLORO 2 HYDROXYBENZYL) 1 (4 FLUOROBENZYL) 3 PHENYLUREA; 1 (3,5 DICHLORO 2 HYDROXYBENZYL) 1 (4 HYDROXYBENZYL) 3 PHENYLUREA; 1 (4 FLUOROBENZYL) 1 (2 HYDROXY 3,5 DIMETHYLBENZYL) 3 PHENYLTHIOUREA; 1 (4 FLUOROBENZYL) 1 (2 HYDROXY 5 METHYLBENZYL) 3 PHENYLTHIOUREA; 1 (4 FLUOROBENZYL) 1 (2 HYDROXY 5 METHYLBENZYL) 3 PHENYLUREA; 1 (5 BROMO 2 HYDROXYBENZYL) 1 (4 FLUOROBENZYL) 3 PHENYLTHIOUREA; 1 (5 BROMO 2 HYDROXYBENZYL) 1 (4 FLUOROBENZYL) 3 PHENYLUREA; 1 (5 BROMO 2 HYDROXYBENZYL) 1 (4 HYDROXYBENZYL) 3 PHENYLTHIOUREA; 1 (5 BROMO 2 HYDROXYBENZYL) 1 (4 HYDROXYBENZYL) 3 PHENYLUREA; 1 (5 BROMO 2 HYDROXYBENZYL) 1 BUTYL 3 PHENYLUREA; 1 (5 CHLORO 2 HYDROXYBENZYL) 1 (4 FLUOROBENZYL) 3 PHENYLTHIOUREA; 1 (5 CHLORO 2 HYDROXYBENZYL) 1 (4 FLUOROBENZYL) 3 PHENYLUREA; 1 (5 CHLORO 2 HYDROXYBENZYL) 1 (4 HYDROXYBENZYL) 3 PHENYLTHIOUREA; 1 (5 CHLORO 2 HYDROXYBENZYL) 1 (4 HYDROXYBENZYL) 3 PHENYLUREA; 1 BUTYL 1 (2 HYDROXY 3,5 DIMETHYLBENZYL) 3 PHENYLUREA; 1 BUTYL 1 (2 HYDROXY 5 METHYLBENZYL) 3 PHENYLUREA; 1 BUTYL 1 (3,5 DIBROMO 2 HYDROXYBENZYL) 3 PHENYLUREA; 1 BUTYL 1 (3,5 DICHLORO 2 HYDROXYBENZYL) 3 PHENYLTUREA; 1 BUTYL 1 (5 CHLORO 2 HYDROXYBENZYL) 3 PHENYLUREA; CARBANILAMIDE DERIVATIVE; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; CELL PROLIFERATION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MODELS, MOLECULAR; NEOPLASMS; PHENYLUREA COMPOUNDS; PROTEIN BINDING; PROTEIN CONFORMATION; RECEPTOR, EPIDERMAL GROWTH FACTOR; RECEPTOR, ERBB-2; STRUCTURE-ACTIVITY RELATIONSHIP; THIOUREA;

EID: 72049109416     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.10.054     Document Type: Article

References (24)

1. Hickey K., Grehan D., Reid I.M., O'Briain S., Walsh T.N., and Hennessy T.P.J. Cancer 74 (1994) 1693
2. Yarden Y., and Sliwkowski M.X. Mol. Cell. Biol. 2 (2001) 127
3. Hynes N.E., and Stern D.F. Biochim. Biophys. Acta 1198 (1994) 165
4. Ross J.S., and Fletcher J.A. Stem Cells 16 (1998) 413
5. Slamon D.J., Clark G.M., Wong S.G., Levin W.J., Ullrich A., and McGuire W.L. Science 235 (1987) 177
6. Slamon D.J., Godolphin W., and Jones L.A. Science 244 (1989) 707
7. Scheurle D., Jahanzeb M., Aronsohn R.S., Watzek L., and Narayanan R.H. Anticancer Res. 20 (2000) 2091
8. Cox G., Vyberg M., Melgaard B., Askaa J., Oster A., and O'Byrne K.J. Int. J. Cancer 92 (2001) 480
9. Gullick W.J. Br. Med. Bull. 47 (1991) 87
10. Moscatello D.K., Holgado-Mudruga M., Godwin A.K., Ramirez G., Gunn G., Zoltick P.W., Biegel J.A., Hayes R.L., and Wong A.J. Cancer Res. 55 (1995) 5536
11. Wikstrand C.J., McLendon R.E., Friedman A., and Bigner D.D. Cancer Res. 57 (1997) 4130
12. Bridges A.J. Curr. Med. Chem. 6 (1999) 825
13. Boschelli D.H. Drugs Future 24 (1999) 515
14. Ullrich A., and Schlessinger J. Cell 61 (1990) 203
15. Hubbard S.R., and Till J.H. Rev. Biochem. 69 (2000) 373
16. Dai Y., Guo Y., Frey R.R., Ji Z., Curtin M.L., Ahmed A.A., Albert D.H., Arnold L., Arries S.S., Barlozzari T., Bauch J.L., Bouska J.J., Bousquet P.F., Cunha G.A., Glaser K.B., Guo J., Li J., Marcotte P.A., Marsh K.C., Moskey M.D., Pease L.J., Stewart K.D., Stoll V.S., Tapang P., Wishart N., Davidsen S.K., and Michaelides M.R. J. Med. Chem. 48 (2005) 6066
17. Dai Y., Hartandi K., Ji Z., Ahmed A.A., Albert D.H., Arnold L., Arries S.S., Barlozzari T., Bauch J.L., Bouska J.J., Bousquet P.F., Cunha G.A., Glaser K.B., Guo J., Li J., Marcotte P.A., Marsh K.C., Moskey M.D., Pease L.J., Stewart K.D., Stoll V.S., Tapang P., Wishart N., Davidsen S.K., and Michaelides M.R. J. Med. Chem. 50 (2007) 1584
18. Li H.Q., Yan T., Lv P.C., and Zhu H.L. Anti-Cancer Agents Med. Chem. 9 (2009) 471
19. Li H.Q., Zhu T.T., Yan T., Luo Y., and Zhu H.L. Eur. J. Med. Chem. 44 (2009) 453
20. Cao P., Huang X.F., Ding H., Ge H.M., Li H.Q., Ruan B.F., and Zhu H.L. Chem. Biodivers. 4 (2007) 881
21. Shi L., Ge H.M., Tan S.H., Li H.Q., Song Y.C., Zhu H.L., and Tan R.X. Eur. J. Med. Chem. 42 (2007) 558
22. Fátima C., Raul S.M., Mónica C., Miren K.U., Xavier S., Imanol T., and Esther D. J. Org. Chem. 70 (2005) 3178
23. Jeffrey D.S., Christopher G.V.S., and Caldwell W.S. J. Med. Chem. 42 (1999) 3066
24. Tsou H.-R., Mamuya N., Johnson B.D., Reich M.F., Gruber B.C., Ye F., Nilakantan R., Shen R., Discafani C., DeBlanc R., Davis R., Koehn F.E., Greenberger L.M., Wang Y.-F., and Wissner A. J. Med. Chem. 44 (2001) 2719