1-Acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles: Exhibiting anticancer activity through intracellular ROS scavenging and the mitochondria-dependent death pathway

Archiv der Pharmazie

Volumn 347, Issue 10, 2014, Pages 717-727

  Alex, Jimi M ^a   Singh, Sandeep ^a   Kumar, Raj ^a  

^a CENTRAL UNIVERSITY OF PUNJAB   (India)

Author keywords

Antiproliferative; MCF cell lines; Mitochondria dependent cell death; Pyrazoles; Synthesis

Indexed keywords

1 ACETYL 3,5 DIARYL 4,5 DIHYDRO(1H)PYRAZOLE DERIVATIVE; 1 [3 (2,4 DICHLOROPHENYL) 5 (FURAN 2 YL) 4,5 DIHYDRO(1H)PYRAZOL 1 YL]ETHANONE; 1 [3 (2,4 DICHLOROPHENYL) 5 (THIOPHEN 2 YL) 4,5 DIHYDRO(1H)PYRAZOL 1 YL]ETHANONE; 1 [3 (4 BROMOPHENYL) 5 (FURAN 2 YL) 4,5 DIHYDRO(1H)PYRAZOL 1 YL]ETHANONE; 1 [3 (4 BROMOPHENYL) 5 (THIOPHEN 2 YL) 4,5 DIHYDRO(1H)PYRAZOL 1 YL]ETHANONE; 1 [3 (4 CHLOROPHENYL) 5 (FURAN 2 YL) 4,5 DIHYDRO(1H)PYRAZOL 1 YL]ETHANONE; 1 [3 (4 CHLOROPHENYL) 5 (THIOPHEN 2 YL) 4,5 DIHYDRO(1H)PYRAZOL 1 YL]ETHANONE; 1 [3 (4 METHOXYPHENYL) 5 (THIOPHEN 2 YL) 4,5 DIHYDRO(1H)PYRAZOL 1 YL]ETHANONE; 1 [3 (PYRIDIN 2 YL) 5 (THIOPHEN 2 YL) 4,5 DIHYDRO(1H)PYRAZOL 1 YL]ETHANONE; 1 [3 PHENYL 5 (THIOPHEN 2 YL) 4,5 DIHYDRO(1H)PYRAZOL 1 YL]ETHANONE; 1 [5 (4 CHLOROPHENYL) 3 (THIOPHEN 2 YL) 4,5 DIHYDRO(1H)PYRAZOL 1 YL]ETHANONE; 1 [5 (FURAN 2 YL) 3 (4 METHOXYPHENYL) 4,5 DIHYDRO(1H)PYRAZOL 1 YL]ETHANONE; 1 [5 (FURAN 2 YL) 3 (4 TOLYL) 4,5 DIHYDRO(1H)PYRAZOL 1 YL]ETHANONE; 1 [5 (FURAN 2 YL) 3 (PYRIDIN 3 YL) 4,5 DIHYDRO(1H)PYRAZOL 1YL]ETHANONE; 1 [5 (THIOPHEN 2 YL) 3 (4 TOLYL) 4,5 DIHYDRO(1H)PYRAZOL 1 YL]ETHANONE; 1 [5 PHENYL 3 (PYRIDIN 2 YL) 4,5 DIHYDRO(1H)PYRAZOL 1 YL]ETHANONE; 1 [5 PHENYL 3 (THIOPHEN 2 YL) 4,5 DIHYDRO(1H)PYRAZOL 1 YL]ETHANONE; ANTINEOPLASTIC AGENT; ETOPOSIDE; PYRAZOLE DERIVATIVE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG; SCAVENGER;

A549 CELL LINE; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CARCINOGENICITY; CELL DEATH; CONTROLLED STUDY; CRYSTALLIZATION; CYCLIZATION; DRUG ACETYLATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC50; MCF 7 CELL LINE; MITOCHONDRIAL MEMBRANE POTENTIAL; MITOCHONDRION; OXIDATIVE STRESS; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; APOPTOSIS; CELL PROLIFERATION; CHEMICAL STRUCTURE; DOSE RESPONSE; DRUG DESIGN; DRUG EFFECTS; METABOLISM; NEOPLASM; PATHOLOGY; SYNTHESIS;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; FREE RADICAL SCAVENGERS; HUMANS; INHIBITORY CONCENTRATION 50; MCF-7 CELLS; MEMBRANE POTENTIAL, MITOCHONDRIAL; MITOCHONDRIA; MOLECULAR STRUCTURE; NEOPLASMS; OXIDATIVE STRESS; PYRAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84908049543     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.201400199     Document Type: Article

References (44)

1. R. W. Ruddon, in Cancer Biology, Oxford University Press, New York 2007.
2. R. Siegel, J. Ma, Z. Zou, A. Jemal, CA: Cancer J. Clin. 2014, 64, 9-29.
3. D. Hanahan, R. A. Weinberg, Cell 2011, 144, 646-674.
4. W. A. Denny, Anti-Cancer Drug Des. 1989, 4, 241-263.
5. M. J. Moore, D. Goldstein, J. Hamm, A. Figer, J. R. Hecht, S. Gallinger, H. J. Au, P. Murawa, D. Walde, R. A. Wolff, J. Clin. Oncol. 2007, 25, 1960-1966.
6. N. J. Robert, V. Diéras, J. Glaspy, A. M. Brufsky, I. Bondarenko, O. N. Lipatov, E. A. Perez, D. A. Yardley, S. Y. Chan, X. Zhou, J. Clin. Oncol. 2011, 29, 1252-1260.
7. D. J. Kuhn, Q. Chen, P. M. Voorhees, J. S. Strader, K. D. Shenk, C. M. Sun, S. D. Demo, M. K. Bennett, F. W. B. van Leeuwen, A. A. Chanan-Khan, Blood 2007, 110, 3281-3290.
8. P. G. Richardson, B. Barlogie, J. Berenson, S. Singhal, S. Jagannath, D. Irwin, S. V. Rajkumar, G. Srkalovic, M. Alsina, R. Alexanian, N. Engl. J. Med. 2003, 348, 2609-2617.
9. C. B. Yoo, P. A. Jones, Nat. Rev. 2006, 5, 37-50.
10. F. Zagouri, T. N. Sergentanis, D. Chrysikos, M. Filipits, R. Bartsch, Gynecol. Oncol. 2012, 127, 662-672.
11. N. M. N. Hari, V. Pratheepa, M. Ramos, V. Vasconcelos, P. Fernandes, Curr. Drug Targets 2014, 15, 681-688.
12. W. R. Pitt, D. M. Parry, B. G. Perry, C. R. Groom, J. Med. Chem. 2009, 52, 2952-2963.
13. A. Gomtsyan, Chem. Heterocycl. Compd. 2012, 48, 7-10.
14. J. M. Alex, R. Kumar, J. Enzyme Inhib. Med. Chem. 2014, 29, 427-442.
15. R. Brown, R. Fischer, J. Blunk, K. D. Berlin, K. Ramalingam, N. N. Durham, Proc. Okla. Acad. Sci. 1976, 56, 15-17.
16. N. N. Durham, R. W. Chesnut, D. F. Haslam, K. D. Berlin, Ann. Okla. Acad. Sci. 1974, 4, 77-86.
17. V. Sharma, V. Kumar, P. Kumar, Anticancer Agents Med. Chem. 2013, 13, 422-432.
18. B. P. Bandgar, S. S. Gawande, R. G. Bodade, N. M. Gawande, C. N. Khobragade, Bioorg. Med. Chem. 2009, 17, 8168-8173.
19. U. K. Jain, R. K. Bhatia, A. R. Rao, R. Singh, A. K. Saxena, I. Sehar, Trop. J. Pharm. Res. 2014, 13, 73-80.
20. A. Repanas, A. Katsori, D. Hadjipavlou-Litina, Mini Rev. Med. Chem. 2013, 13, 952-970.
21. B. Bhat, K. Dhar, S. Puri, A. Saxena, M. Shanmugavel, G. Qazi, Bioorg. Med. Chem. Lett. 2005, 15, 3177-3180.
22. T. Liu, R. Cui, J. Chen, J. Zhang, Q. He, B. Yang, Y. Hu, Arch. Pharm. 2011, 344, 279-286.
23. C. Congiu, V. Onnis, L. Vesci, M. Castorina, and, P. C. Bioorg, Med. Chem. 2010, 18, 6238-6248.
24. R. LeBlanc, J. Dickson, T. Brown, M. Stewart, H. N. Pati, D. VanDerveer, H. Arman, J. Harris, W. Pennington, H. L. Holt, Jr., Bioorg. Med. Chem. 2005, 13, 6025-6034.
25. M. Lee, O. Brockway, A. Dandavati, S. Tzou, R. Sjoholm, V. Satam, C. Westbrook, S. L. Mooberry, M. Zeller, B. Babu, Eur. J. Med. Chem. 2011, 46, 3099-3104.
26. K. Nepali, G. Singh, A. Turan, A. Agarwal, S. Sapra, R. Kumar, U. C. Banerjee, P. K. Verma, N. K. Satti, M. K. Gupta, Bioorg. Med. Chem. 2011, 19, 1950-1958.
27. A. T. Baviskar, U. C. Banerjee, M. Gupta, R. Singh, S. Kumar, M. K. Gupta, S. Kumar, S. K. Raut, M. Khullar, S. Singh, Bioorg. Med. Chem. 2013, 21, 5782-5793.
28. Y. Shi, X. Fu, Y. Hua, Y. Han, Y. Lu, J. Wang, PLoS ONE 2012, 7, e33358.
29. J. A. Aka, S.-X. Lin, PLoS ONE 2012, 7, e31532.
30. S. Blein, S. Berndt, A. D. Joshi, D. Campa, R. G. Ziegler, E. Riboli, D. G. Cox, Free Radic. Res. 2014, 48, 380-386.
31. G. Borges Bubols, D. da Rocha Vianna, A. Medina-Remon, G. von Poser, R. Maria Lamuela-Raventos, V. Lucia Eifler-Lima, S. Cristina Garcia, Mini Rev. Med. Chem. 2013, 13, 318-334.
32. M. Valko, D. Leibfritz, J. Moncol, M. T. Cronin, M. Mazur, J. Telser, Int. J. Biochem. Cell Biol. 2007, 39, 44-84.
33. V. Fuchs-Tarlovsky, Nutrition 2013, 29, 15-21.
34. C. Adrain, S. J. Martin, Trends Biochem. Sci. 2001, 26, 390-397.
35. X. Jiang, X. Wang, Annu. Rev. Biochem. 2004, 73, 87-106.
36. K. M. Heiskanen, M. B. Bhat, H.-W. Wang, J. Ma, A.-L. Nieminen, J. Biol. Chem. 1999, 274, 5654-5658.
37. M. Reers, T. W. Smith, L. B. Chen, Biochemistry 1991, 30, 4480-4486.
38. A. K. Tengli, S. Badami, B. R. P. Kumar, S. K. H. Dongre, S. Ravi, A. K. T. Durai, Indian J. Heterocycl. Chem. 2007, 16, 333-336.
39. M. M. El-Kerdawy, M. N. Tolba, A. A. El-Agamey, Egypt. J. Chem. 1976, 17, 7-14.
40. H.-M. Guo, Acta Crystallogr. 2007, 63, 3165.
41. D. M. Ferguson, J. Goodell, Regents of the University of Minnesota. Pyrazoline derivatives for treatment of viral infections. USA. Patent WO 2007038425, 2007.
42. A. V. Ingle, A. G. Doshi, A. W. Raut, Orient. J. Chem. 2010, 26, 951-9957.
43. A. D. B. Ciupa, A. Paul, M. F. Mahon, P. J. Wood, L. Caggiano, Med. Chem. Commun. 2013, 4, 956-996.
44. A. M. Attia, M. Michael, Acta. Chim. Hung. 1983, 114, 337-348.