Optimization of 2-(3-(arylalkyl amino carbonyl) phenyl)-3-(2-methoxyphenyl) -4-thiazolidinone derivatives as potent antitumor growth and metastasis agents

European Journal of Medicinal Chemistry

Volumn 80, Issue , 2014, Pages 340-351

  Wu, Jing ^a   Yu, Linxi ^a   Yang, Feifei ^a   Li, Jingjie ^a   Wang, Peng ^a   Zhou, Wenbo ^a   Qin, Liwen ^a   Li, Yunqi ^a   Luo, Jian ^a   Yi, Zhengfang ^a   Liu, Mingyao ^a,b   Chen, Yihua ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b TEXAS A AND M HEALTH SCIENCE CENTER   (United States)

Author keywords

Antitumor growth and metastasis; Structure activity relationships; Thiazolidinone derivatives

Indexed keywords

2 (3 N,N DIALLYLAMINO CARBONYLPHENYL) 3 (2 METHOXYPHENYL) 4 THIAZOLIDINONE; 2 (3 N,N DIETHYLAMINO CARBONYLPHENYL) 3 (2 METHOXYPHENYL) 4 THIAZOLIDINONE; 2 [3 (1 PIPERIDINYL)CARBONYLPHENYL] 3 (2 METHOXYPHENYL) 4 THIAZOLIDINONE; 2 [3 (2 BROMOPHENYLETHYL AMINO CARBONYL) PHENYL] 3 (2 METHOXYPHENYL) 4 THIAZOLIDINONE; 2 [3 (4 BROMOPHENYLETHYL AMINO CARBONYL) PHENYL] 3 (2 METHOXYPHENYL) 4 THIAZOLIDINONE; 2 [3 (4 CHLOROPHENYLETHYL AMINO CARBONYL) PHENYL] 3 (2 METHOXYPHENYL) 4 THIAZOLIDINONE; 2 [3 (4 FLUOROPHENYLETHYL AMINO CARBONYL) PHENYL] 3 (2 METHOXYPHENYL) 4 THIAZOLIDINONE; 2 [3 (4 HYDROXYPHENYLETHYL AMINO CARBONYL) PHENYL] 3 (2 METHOXYPHENYL) 4 THIAZOLIDINONE; 2 [3 (4 METHOXYPHENYLETHYL AMINO CARBONYL) PHENYL] 3 (2 METHOXYPHENYL) 4 THIAZOLIDINONE; 2 [3 (BENZYL AMINO CARBONYL)PHENYL] 3 (2 METHOXYPHENYL) 4 THIAZOLIDINONE; 2 [3 (PHENYL AMINO CARBONYL)PHENYL] 3 (2 METHOXYPHENYL) 4 THIAZOLIDINONE; 2 [3 (PHENYLETHYL AMINO CARBONYL)PHENYL] 3 (2 METHOXYPHENYL) 4 THIAZOLIDINONE; 2 [3 (PHENYLPROPYL AMINO CARBONYL)PHENYL] 3 (2 METHOXYPHENYL) 4 THIAZOLIDINONE; 3 [3 (2 METHOXYPHENYL) 4 OXO 2 THIAZOLIDINYL]BENZOIC ACID; 4 THIAZOLIDINONE DERIVATIVE; ANTINEOPLASTIC AGENT; UNCLASSIFIED DRUG; THIAZOLIDINE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS ASSAY; ARTICLE; BIOLUMINESCENCE; BREAST CANCER; CANCER CELL; CANCER GROWTH; CELL CYCLE ARREST; CELL MIGRATION; CELL PROLIFERATION; CONTROLLED STUDY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROLYSIS; IC 50; LUNG SMALL CELL CANCER; M PHASE CELL CYCLE CHECKPOINT; METASTASIS; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; SURVIVAL RATE; ANIMAL; BREAST TUMOR; CELL CYCLE CHECKPOINT; CHEMISTRY; DRUG DESIGN; DRUG EFFECTS; DRUG SCREENING; FEMALE; LUNG TUMOR; PATHOLOGY; SYNTHESIS; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL CYCLE CHECKPOINTS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DESIGN; FEMALE; HUMANS; LUNG NEOPLASMS; MICE; NEOPLASM METASTASIS; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLIDINES; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84899889800     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.04.068     Document Type: Article

References (33)

1. A. Jemal, R. Siegel, J. Xu, and E. Ward Cancer statistics, 2010 Ca - a Cancer Journal for Clinicians 60 2010 277 300
2. A. Jemal, R. Siegel, E. Ward, Y. Hao, J. Xu, T. Murray, and M.J. Thun Cancer statistics, 2008 Ca - a Cancer Journal for Clinicians 58 2008 71 96 (Pubitemid 351521864)
3. T. Mitsudomi Advances in target therapy for lung cancer Japanese Journal of Clinical Oncology 40 2010 101 106
4. S.G. Spiro, N.T. Tanner, G.A. Silvestri, S.M. Janes, E. Lim, J.F. Vansteenkiste, and R. Pirker Lung cancer: progress in diagnosis, staging and therapy Respirology: Official Journal of the Asian Pacific Society of Respirology 15 2010 44 50
5. E. Warner, A. Jotkowitz, and N. Maimon Lung cancer screening-are we there yet? European Journal of Internal Medicine 21 2010 6 11
6. Helen M. Coley Mechanisms and strategies to overcome chemotherapy resistance in metastatic breast cancer Cancer Treatment Reviews 34 2008 378 390
7. K. McPherson, C.M. Steel, and J.M. Dixon ABC of breast diseases. Breast cancer-epidemiology, risk factors, and genetics Bmj: British Medical Journal 321 2000 624 628
8. K.K. Deeb, A.M. Michalowska, C.Y. Yoon, S.M. Krummey, M.J. Hoenerhoff, C. Kavanaugh, M.C. Li, F.J. Demayo, I. Linnoila, C.X. Deng, E.Y. Lee, D. Medina, J.H. Shih, and J.E. Green Identification of an integrated SV40 T/t-antigen cancer signature in aggressive human breast, prostate, and lung carcinomas with poor prognosis Cancer Research 67 2007 8065 8080 (Pubitemid 47395141)
9. C. To, B.H. Shilton, and G.M. Di Guglielmo Synthetic triterpenoids target the Arp2/3 complex and inhibit branched actin polymerization The Journal of Biological Chemistry 285 2010 27944 27957
10. G. Christofori New signals from the invasive front Nature 441 2006 444 450 (Pubitemid 44050139)
11. P. Mehlen, and A. Puisieux Metastasis: a question of life or death Nature Reviews Cancer 6 2006 449 458
12. C. Zheng, Y. Fang, W. Tong, G. Li, H. Wu, W. Zhou, Q. Lin, F. Yang, Z. Yang, P. Wang, Y. Peng, X. Pang, Z. Yi, J. Luo, M. Liu, and Y. Chen Synthesis and biological evaluation of novel tetrahydro-beta-carboline derivatives as anti-tumor growth and metastasis agents through inhibiting the transforming growth factor-beta signaling pathway Journal of Medicinal Chemistry 57 2014 600 612
13. A. Verma, and S.K. Saraf 4-thiazolidinone-a biologically active scaffold European Journal of Medicinal Chemistry 43 2008 897 905
14. B. Goel, T. Ram, R. Tyagi, E. Bansal, A. Kumar, D. Mukherjee, and J.N. Sinha 2-Substituted-3-(4-bromo-2-carboxyphenyl)-5-methyl-4-thiazolidinones as potential anti-inflammatory agents European Journal of Medicinal Chemistry 34 1999 265 269
15. A.A. Elbarbary, A.I. Khodair, E.B. Pedersen, and C. Nielsen Synthesis and evaluation of antiviral activity of 2′-deoxyuridines with 5-methylene-2-thiohydantoin substituents in the 5-position Monatshefte Fur Chemie 125 1994 593 598
16. R. Ottana, S. Carotti, R. Maccari, I. Landini, G. Chiricosta, B. Caciagli, M.G. Vigorita, and E. Mini In vitro antiproliferative activity against human colon cancer cell lines of representative 4-thiazolidinones. Part I Bioorganic & Medicinal Chemistry Letters 15 2005 3930 3933 (Pubitemid 41095497)
17. Y.J. Chen, C.C. Chen, T.K. Li, P.H. Wang, L.R. Liu, F.Y. Chang, Y.C. Wang, Y.H. Yu, S.P. Lin, H.J. Mersmann, and S.T. Ding Docosahexaenoic acid suppresses the expression of FoxO and its target genes The Journal of Nutritional Biochemistry 23 2012 1609 1616
18. T. Zhang, J. Li, Y. Dong, D. Zhai, L. Lai, F. Dai, H. Deng, Y. Chen, M. Liu, and Z. Yi Cucurbitacin E inhibits breast tumor metastasis by suppressing cell migration and invasion Breast Cancer Research and Treatment 135 2012 445 458
19. G.J. Murphy, and J.C. Holder PPAR-gamma agonists: therapeutic role in diabetes, inflammation and cancer Trends in Pharmacological Sciences 21 2000 469 474
20. V. Gududuru, E. Hurh, J.T. Dalton, and D.D. Miller Synthesis and antiproliferative activity of 2-aryl-4-oxo-thiazolidin-3-yl-amides for prostate cancer Bioorganic & Medicinal Chemistry Letters 14 2004 5289 5293 (Pubitemid 39348915)
21. V. Gududuru, E. Hurh, J.T. Dalton, and D.D. Miller Discovery of 2-arylthiazolidine-4-carboxylic acid amides as a new class of cytotoxic agents for prostate cancer Journal of Medicinal Chemistry 48 2005 2584 2588 (Pubitemid 40516447)
22. M.M. Kamel, H.I. Ali, M.M. Anwar, N.A. Mohamed, and A.M. Soliman Synthesis, antitumor activity and molecular docking study of novel sulfonamide-Schiff's bases, thiazolidinones, benzothiazinones and their C-nucleoside derivatives European Journal of Medicinal Chemistry 45 2010 572 580
23. B.J. Nolen, N. Tomasevic, A. Russell, D.W. Pierce, Z. Jia, C.D. McCormick, J. Hartman, R. Sakowicz, and T.D. Pollard Characterization of two classes of small molecule inhibitors of Arp2/3 complex Nature 460 2009 1031 1034
24. O. Akin, and R.D. Mullins Capping protein increases the rate of actin-based motility by promoting filament nucleation by the Arp2/3 complex Cell 133 2008 841 851 (Pubitemid 351707682)
25. J. Yu, Q. Wang, X. Shi, X. Ma, H. Yang, Y.G. Chen, and X. Fang Single-molecule force spectroscopy study of interaction between transforming growth factor beta1 and its receptor in living cells The Journal of Physical Chemistry: B 111 2007 13619 13625 (Pubitemid 350275466)
26. E.D. Goley, and M.D. Welch The ARP2/3 complex: an actin nucleator comes of age Nature Reviews. Molecular Cell Biology 7 2006 713 726 (Pubitemid 44450456)
27. T. Srivastava, W. Haq, and S.B. Katti Carbodiimide mediated synthesis of 4-thiazolidinones by one-pot three-component condensation Tetrahedron 58 2002 7619 7624 (Pubitemid 35251835)
28. A.R. Surrey 4-Thiazolidones. V. The reaction of some semicarbazones with thioglycolic acid Journal of the American Chemical Society 74 1952 3450 3451
29. A.R. Surrey, and R.A. Cutler 4-Thiazolidones. VI.1 the preparation of some 2-substituted derivatives Journal of the American Chemical Society 76 1954 578 580
30. A.K. Yadav, M. Kumar, T. Yadav, and R. Jain An ionic liquid mediated one-pot synthesis of substituted thiazolidinones and benzimidazoles Tetrahedron Letters 50 2009 5031 5034
31. Z. Zhou, and Z. Ruan Multicontext wavelet-based thresholding segmentation of brain tissues in magnetic resonance images Magnetic Resonance Imaging 25 2007 381 385 (Pubitemid 46413640)
32. M. Bendre, D. Gaddy, R.W. Nicholas, and L.J. Suva Breast cancer metastasis to bone: it is not all about PTHrP Clinical Orthopaedics and Related Research 2003 S39 S45
33. L. Catley, E. Weisberg, Y.T. Tai, P. Atadja, S. Remiszewski, T. Hideshima, N. Mitsiades, R. Shringarpure, R. LeBlanc, D. Chauhan, N.C. Munshi, R. Schlossman, P. Richardson, J. Griffin, and K.C. Anderson NVP-LAQ824 is a potent novel histone deacetylase inhibitor with significant activity against multiple myeloma Blood 102 2003 2615 2622 (Pubitemid 37193603)