New triarylpyrazoles as broad-spectrum anticancer agents: Design, synthesis, and biological evaluation

European Journal of Medicinal Chemistry

Volumn 65, Issue , 2013, Pages 315-322

  El Gamal, Mohammed I ^a,b,c   Park, Yi Seul ^a,d   Chi, Dae Yoon ^d   Yoo, Kyung Ho ^a   Oh, Chang Hyun ^a,b  

^a Korea Institute of Science and Technology   (South Korea)

^b University of Science and Technology (UST)   (South Korea)

^c Mansoura University 35516   (Egypt)

^d Sogang University   (South Korea)

Author keywords

1,3,4 Triarylpyrazole; Anticancer; Cytotoxicity; Diarylamide; Diarylurea

Indexed keywords

1 [3 [3 (4 CHLORO 3 HYDROXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL] 3 (3,4 DICHLOROPHENYL)UREA; 1 [3 [3 (4 CHLORO 3 HYDROXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL] 3 PHENYLUREA; 1 [3 [3 (4 CHLORO 3 HYDROXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL] 3 [3 (TRIFLUOROMETHYL)PHENYL]UREA; 1 [3 [3 (4 CHLORO 3 METHOXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL] 3 (3,4 DICHLOROPHENYL)UREA; 1 [3 [3 (4 CHLORO 3 METHOXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL] 3 PHENYLUREA; 1 [3 [3 (4 CHLORO 3 METHOXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL] 3 [3 (TRIFLUOROMETHYL)PHENYL]UREA; 1 [3,5 BIS(TRIFLUOROMETHYL)PHENYL] 3 [3 [3 (4 CHLORO 3 HYDROXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL]UREA; 1 [3,5 BIS(TRIFLUOROMETHYL)PHENYL] 3 [3 [3 (4 CHLORO 3 METHOXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL]UREA; 1 [4 CHLORO 3 (TRIFLUOROMETHYL)PHENYL] 3 [3 [3 (4 CHLORO 3 HYDROXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL]UREA; 1 [4 CHLORO 3 (TRIFLUOROMETHYL)PHENYL] 3 [3 [3 (4 CHLORO 3 METHOXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL]UREA; 4 BROMO N [3 [3 (4 CHLORO 3 HYDROXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL] 3 METHYLBENZAMIDE; 4 BROMO N [3 [3 (4 CHLORO 3 METHOXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL] 3 METHYLBENZAMIDE; 4 CHLORO N [3 [3 (4 CHLORO 3 HYDROXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL] 3 (TRIFLUOROMETHYL)BENZAMIDE; 4 CHLORO N [3 [3 (4 CHLORO 3 METHOXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL] 3 (TRIFLUOROMETHYL)BENZAMIDE; ANTINEOPLASTIC AGENT; N [3 [3 (4 CHLORO 3 HYDROXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL] 3 (TRIFLUOROMETHYL)BENZAMIDE; N [3 [3 (4 CHLORO 3 HYDROXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL] 4 MORPHOLINO 3 (TRIFLUOROMETHYL)BENZAMIDE; N [3 [3 (4 CHLORO 3 HYDROXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL] BENZAMIDE; N [3 [3 (4 CHLORO 3 METHOXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL] 3 (TRIFLUOROMETHYL)BENZAMIDE; N [3 [3 (4 CHLORO 3 METHOXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL] 4 MORPHOLINO 3 (TRIFLUOROMETHYL)BENZAMIDE; N [3 [3 (4 CHLORO 3 METHOXYPHENYL) 4 (PYRIDIN 4 YL) 1H PYRAZOL 1 YL]PHENYL]BENZAMIDE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; MELANOMA CELL;

EID: 84878411252     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.04.067     Document Type: Article

References (24)

1. WHO website. http://www.who.int/mediacentre/factsheets/fs297/en/.
2. M.-H. Jung, C.-H. Oh, Bull. Korean Chem. Soc. 29 (2008) 2231-2236.
3. M.-H. Jung, H. Kim, W.-K. Choi, M.I. El-Gamal, J.-H. Park, K.H. Yoo, T.B. Sim, S.H. Lee, D. Baek, J.-M. Hah, J.-H. Cho, C.-H. Oh, Bioorg. Med. Chem. Lett. 19 (2009) 6538-6543.
4. B.S. Nam, H. Kim, C.-H. Oh, S.H. Lee, S.J. Cho, T.B. Sim, J.-M. Hah, D.J. Kim, J.H. Choi, K.H. Yoo, Bioorg. Med. Chem. Lett. 19 (2009) 3517-3520.
5. D.-Q. Song, N.-N. Du, Y.-M. Wang, W.-Y. He, E.-Z. Jiang, S.-X. Cheng, Y.-X. Wang, Y.-H. Li, Y.-P. Wang, X. Li, J.-D. Jiang, Bioorg. Med. Chem. 17 (2009) 3873-3878.
6. W.-K. Choi, C.-H. Oh, Bull. Korean Chem. Soc. 30 (2009) 2027-2031.
7. H.J. Kim, M.-H. Jung, H. Kim, M.I. El-Gamal, T.B. Sim, S.H. Lee, J.H. Hong, J.-M. Hah, J.-H. Cho, J.H. Choi, K.H. Yoo, C.-H. Oh, Bioorg. Med. Chem. Lett. 20 (2010) 413-417.
8. H. Yu, Y. Jung, H. Kim, J. Lee, C.-H. Oh, K.H. Yoo, T. Sim, J.-M. Hah, Bioorg. Med. Chem. Lett. 20 (2010) 3805-3808.
9. J. Lee, H. Kim, H. Yu, J.Y. Chung, C.-H. Oh, K.H. Yoo, T. Sim, J.-M. Hah, Bioorg. Med. Chem. Lett. 20 (2010) 1573-1577.
10. P. Yao, X. Zhai, D. Liu, B.H. Qi, H.L. Tan, Y.C. Jin, P. Gong, Arch. Pharm. Chem. Life Sci. 343 (2010) 17-23.
11. M.I. El-Gamal, M.-H. Jung, W.S. Lee, T. Sim, K.H. Yoo, C.-H. Oh, Eur. J. Med. Chem. 46 (2011) 3218-3226.
12. W.-K. Choi, M.I. El-Gamal, H.S. Choi, D. Baek, C.-H. Oh, Eur. J. Med. Chem. 46 (2011) 5754-5762.
13. H.J. Kim, H.J. Cho, H. Kim, M.I. El-Gamal, C.-H. Oh, S.H. Lee, T. Sim, J.-M. Hah, K.H. Yoo, Bioorg. Med. Chem. Lett. 22 (2012) 3269-3273.
14. M.I. El-Gamal, C.-H. Oh, Bull. Korean Chem. Soc. 33 (2012) 1571-1576.
15. M.-H. Jung, M.I. El-Gamal, M.S. Abdel-Maksoud, T. Sim, K.H. Yoo, C.-H. Oh, Bioorg. Med. Chem. Lett. 22 (2012) 4362-4367.
16. W.-K. Choi, M.I. El-Gamal, H.S. Choi, J.H. Hong, D. Baek, K. Choi, C.-H. Oh, Bull. Korean Chem. Soc. 33 (2012) 2991-2998.
17. H.J. Cho, M.I. El-Gamal, C.-H. Oh, G. Kim, J.H. Hong, H.S. Choi, K.H. Yoo, Bull. Korean Chem. Soc. 33 (2012) 3635-3639.
18. S. Wilhelm, C. Carter, M. Lynch, T. Lowinger, J. Dumas, R.A. Smith, B. Schwartz, R. Simantov, S. Kelley, Nat. Rev. Drug Discov. 5 (2006) 835-844.
19. DGNews website. http://www.pslgroup.com/news/content.nsf/medicalnews/ 852571020057CCF685257384005A45B1?OpenDocument&id=&count=10.
20. R. Capdeville, E. Buchdunger, J. Zimmermann, A. Matter, Nat. Rev. Drug Discov. 1 (2002) 493-502.
21. J. Weinstock, D. Gaitanopoulos, H.J. Oh, F.R. Pfeiffer, C.B. Karash, J.W. Venslavsky, H.M. Sarau, K.E. Flaim, J.P. Hieble, C. Kaiser, J. Med. Chem. 29 (1986) 1615-1627.
22. F. Claudi, G. Giorgioni, A. Di Stefano, M.P. Abbracchio, A.M. Paoletti, W. Balduini, J. Med. Chem. 35 (1992) 4408-4414.
23. M.I. El-Gamal, H.S. Choi, H.-G. Cho, J.H. Hong, K.H. Yoo, C.-H. Oh, Arch. Pharm. Chem. Life Sci. 344 (2011) 745-754.
24. NCI website. www.dtp.nci.nih.gov.