Discovery and optimization of novel dual dithiocarbamates as potent anticancer agents

European Journal of Medicinal Chemistry

Volumn 93, Issue , 2015, Pages 381-391

  Li, Ri Dong ^a   Wang, Hui Ling ^a   Li, Ying Bo ^a,b   Wang, Zhong Qing ^a   Wang, Xin ^a   Wang, Yi Tao ^b   Ge, Ze Mei ^a   Li, Run Tao ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b UNIVERSITY OF MACAU   (Macao)

Author keywords

Anti tumor activity; Dual dithiocarbamate; Structureeactivity relationship; Synthesis

Indexed keywords

2 (1H PYRROLE 2 CARBONYL)PROPANE 1,3 DIYL BIS(DIMETHYLCARBAMODITHIOATE); 2 (2 FLUOROBENZOYL)PROPANE 1,3 DIYL BIS(DIMETHYLCARBAMODITHIOATE); 2 (2 METHOXYBENZOYL)PROPANE 1,3 DIYL BIS(DIMETHYLCARBAMODITHIOATE); 2 (3 METHOXYBENZOYL)PROPANE 1,3 DIYL BIS(DIMETHYLCARBAMODITHIOATE); 2 (4 FLUOROBENZOYL)PROPANE 1,3 DIYL BIS(DIMETHYLCARBAMODITHIOATE); 2 (4 HYDROXYBENZOYL)PROPANE 1,3 DIYL BIS(DIMETHYLCARBAMODITHIOATE); 2 (QUINOLINE 3 CARBONYL)PROPANE 1,3 DIYL BIS(DIETHYLCARBAMODITHIOATE); 2 (QUINOLINE 3 CARBONYL)PROPANE 1,3 DIYL BIS[METHYL(PYRIDIN 3 YLMETHYL)CARBAMODITHIOATE]; 2 (QUINOLINE 3 CARBONYL)PROPANE 1,3 DIYL DIMORPHOLINE 4 CARBODITHIOATE; 2 (QUINOLINE 3 CARBONYL)PROPANE 1,3 DIYL DIPIPERIDINE 1 CARBODITHIOATE; 2 (QUINOLINE 3 CARBONYL)PROPANE 1,3 DIYL DIPYRROLIDINE 1 CARBODITHIOATE; 2 (QUINOLINE 3 CARBONYL)PROPANE 1,3 DIYL DITHIOMORPHOLINE 4 CARBODITHIOATE; 2 (QUINOLINE 3 CARBONYL)PROPANE 1,3 DIYL METHYLPIPERAZINE 1 CARBODITHIOATE); 2 (THIAZOLE 2 CARBONYL)PROPANE 1,3 DIYL BIS(DIMETHYLCARBAMODITHIOATE); 2 BENZOYLPROPANE 1,3 DIYL BIS(DIMETHYLCARBAMODITHIOATE); 2 NICOTINOYLPROPANE 1,3 DIYL BIS(DIMETHYLCARBAMODITHIOATE); 2 [4 (BENZYLOXY)BENZOYL]PROPANE 1,3 DIYL BIS(DIMETHYLCARBAMODITHIOATE); AMINE; ANTINEOPLASTIC AGENT; BENZENE; COUMARIN; DIMETHYLAMINE; DITHIOCARBAMIC ACID; METHYL GROUP; MORPHOLINE; PYRIDINE; QUINOLINE; THIAZOLE; THIOPHENE; UNCLASSIFIED DRUG; CARBAMIC ACID DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL LINE; CANCER INHIBITION; DRUG DEVELOPMENT; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; MCF 7 CELL LINE; NON SMALL CELL LUNG CANCER; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; CELL PROLIFERATION; CHEMISTRY; DRUG DESIGN; DRUG EFFECTS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CARBAMATES; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DESIGN; HUMANS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84923608995     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.02.030     Document Type: Article

References (33)

1. H.-Y. Hung, E. Ohkoshi, M. Goto, K.F. Bastow, K. Nakagawa-Goto, K.-H. Lee, Antitumor agents. 293. nontoxicdimethyl-4, 4′-dimethoxy-5, 6, 5′, 6′-dimethy-lenedi oxybiphenyl-2, 2′-dicarboxylate (DDB) analogues chemosensitize multidrug-resistant cancer cells to clinical anticancer drugs, J. Med. Chem. 55 (2012) 5413-5424.
2. D.C. Swinney, J. Anthony, How were new medicines discovered, Nat. Rev. Drug Discov. 10 (2011) 507-519.
3. C. Len, A.S. Boulogne-merlot, D. Postel, G. Ronco, P. Villa, C. Goubert, E. Jeufrault, B. Mathon, H. Simon, Synthesis and antifungal activity of novel bis(dithiocarbamate) derivatives of glycerol, J. Agric. Food Chem. 44 (1996) 2856-2858.
4. H. Imamura, N. Ohtake, R. Nagano, S. Abe, K. Yamada, T. Hashizume, H. Morishima, Dicationic dithiocarbamate carbapenems with anti-MRSA activity, Bioorg. Med. Chem. 9 (2001) 1571-1578.
5. F. Carta, M. Aggarwal, A. Maresca, R. McKenna, E. Masini, CT. Supuran, Di-thiocarbamates strongly inhibit carbonic anhydrases and show antiglaucoma action in vivo, J. Med. Chem. 55 (2012) 1721 e 1730.
6. F. Carta, CT. Supuran, Dithiocarbamates: a new class of carbonic anhydrase inhibitors. Crystallographic and kinetic investigations, Chem. Commun. 48 (2012) 1868-1870.
7. M.A.-H. Zahran, T.A.-R. Salem, R.M. Samaka, H.S. Agwa, A.R. Awad, Design, synthesis and antitumor evaluation of novel thalidomide dithiocarbamate and dithioate analogs against ehrlich ascites carcinoma-induced solid tumor in Swiss albino mice, Bioorg. Med. Chem. 16 (2008) 9708-9718.
8. W. Huang, Y. Ding, Y. Miao, M.Z. Liu, Y. Li, G.F. Yang, Synthesis and antitumor activity of novel dithiocarbamate substituted chromones, Eur. J. Med. Chem. 44 (2009) 3687-3696.
9. (a) S.L. Cao, Y.P. Feng, Y.Y. Jiang, S.Y. Liu, G.Y. Ding, R.T. Li, Synthesis andin vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains, Bioorg. Med. Chem. Lett. 15 (2005) 1915-1917
10. (b) S.L. Cao, Y.P. Feng, X.L. Zheng, Y.Y. Jiang, M. Zhang, Y. Wang, M. Xu, Synthesis of substituted-benzylamino-and heterocyclylmethylamino-carbodithioate derivatives of 4(3H)-quinazolinone and their cytotoxic activity, Arch. Pharm. 339 (2006) 250-254
11. (c) S.L. Cao, Y. Wang, L Zhu, J. Liao, Y.W. Guo, L.L. Chen, H.Q. Liu, X. Xu, Synthesis and cytotoxic activity of N-((2-methyl-4(3H)-quinazolinon-6-yl) methyl)dithiocarbamates, Eur. J. Med. Chem. 45 (2010) 3850-3857
12. (d) S.L. Cao, Y. Han, CZ. Yuan, Y. Wang, Z.-K. Xiahou, J. Liao, R.T. Gao, B.B. Mao, B.L. Zhao, Z.F. Li, X. Xu, Synthesis and antiproliferative activity of 4-substituted-piperazine-1-carbodithioate derivatives of 2, 4-diaminoquinazoline, Eur. J. Med. Chem. 64 (2013) 401-409.
13. X.J. Wang, H.W. Xu, L.L. Guo, X. Guo, CX. Zheng, H.M. Liu, Synthesis and in vitro antitumor activity of new butenolide-containing dithiocarbamates, Bioorg. Med. Chem. Lett. 21 (2011) 3074-3077.
14. (a) Y.C. Duan, Y.C. Ma, E. Zhang, XJ. Shi, M.M. Wang, X.W. Ye, H.M. Liu, Design and synthesis of novel 1, 2, 3-triazole-dithiocarbamate hybrids as potential anticancer agents, Eur. J. Med. Chem. 62 (2013) 11-19
15. (b) Y.C. Duan, Y.C. Zheng, X.C. Li, M.M. Wang, X.W. Ye, Y.Y. Guan, G.Z. Liu, J.X. Zheng, H.M. Liu, Design, synthesis and antiproliferative activity studies of novel 1, 2, 3-triazole-dithiocarbamate-urea hybrids, Eur. J. Med. Chem. 64 (2013) 99-110
16. (c) Y.C. Zheng, Y.C. Duan, J.L. Ma, R.M. Xu, X.L. Zi, W.L. Lv, M.M. Wang, X.W. Ye, S. Zhu, D. Mobley, Y.Y. Zhu, J.W. Wang, J.F. Li, Z.R. Wang, W. Zhao, H.M. Liu, Triazole-dithiocarbamate based selective lysine specific demethylase 1 (LSD1) inactivators inhibit gastric cancer cell growth, invasion, and migration, J. Med. Chem. 56 (2013) 8543-8560.
17. (a) B.G. Guo, Z.M. Ge, T.M. Cheng, R.T. Li, Synthesis and anti-tumor activity of 1, 4-bis[3-(aminodithiocarboxyl)propionyl]piperazine derivatives, Acta Pharmacol. Sin. 36 (2001) 185-187
18. (b) Z.M. Ge, R.T. Li, T.M. Cheng, J.R. Cui, Synthesis and biological activities of dipiperazinium salts containing dithiocarboxyl, Arch. Pharm. Pharm. Med. Chem. 334 (2001) 173-176
19. (c) X.L. Hou, Z.M. Ge, T.M. Wang, W. Guo, J.R. Cui, T.M. Cheng, CS. Lai, R.T. Li, Dithiocarbamic acid esters as anticancer agent. Part 1: 4-Substituted-pipera-zine-1-carbodithioic acid 3-cyano-3, 3-diphenyl-propyl esters, Bioorg. Med. Chem. Lett. 16 (2006) 4214-4219
20. (d) X.L. Hou, Z.M. Ge, T.M. Wang, W. Guo, J. Wu, J.R. Cui, CS. Lai, R.T. Li, Synthesis and structure-activity relationships of a novel class of dithiocarbamic acid esters as anticancer agent, Arch. Pharm. Chem. Life Sci. 11 (2011) 320-332
21. (e) R.D. Li, X. Zhang, Q.Y. Li, Z.M. Ge, R.T. Li, Novel EGFR inhibitors prepared by combination of dithiocarbamic acid esters and 4-anilinoquinazolines, Bioorg. Med. Chem. Lett. 21 (2011) 3637-3640
22. (f) X. Zhang, R.D. Li, K. Qiao, Z.M. Ge, LR. Zhang, T.M. Cheng, R.T. Li, Novel dithiocarbamic acid esters derived from 6-aminomethyl-4-anilinoquinazolines and 6-aminomethyl-4-anilino-3-cyanoquinolines as potent EGFR inhibitors, Arch. Pharm. Chem. Life Sci. 346 (2013) 44-52
23. (g) N. Zhang, W. Guo, L Wang, W. Huang, B. Xu, Z.M. Ge, M. Li, R.T. Li, J.R. Cui, Effect of TM208 on QGY-7703 xenograft tumor growth, Anti-Cancer Drugs 19 (2008) 593-598
24. (h) Y.B. Li, Z.Q. Wang, X. Yan, M.W. Chen, J.L. Bao, G.S. Wu, Z.M. Ge, D.M. Zhou, Y.T. Wang, R.T. Li, IC-4, a new irreversible EGFR inhibitor, exhibits prominent anti-tumor and anti-angiogenesis activities, Cancer Lett. 340 (2013) 88-96.
25. H.N. Pati, U. Das, I.J.R. amirez-E rosa, D.M. Dunlop, R.A. Hickie, J.R. Dimmock, a-substituted 1-aryl-3-dimethylaminopropanone hydrochlorides: potent cyto-toxins towards human WiDr colon cancer cells, Chem. Pharm. Bull. 55 (2007) 511-515.
26. D.I. Perez, V. Palomo, C Perez, C Gil, P.D. Dans, F.J. Luque, S. Conde, A. Martínez, Switching reversibility to irreversibility in glycogen synthase kinase 3 inhibitors: clues for specific design of new compounds, J. Med. Chem. 54 (2011) 4042-4056.
27. S. Patnaik, H.C. Dietz, W. Zheng, C Austin, J.J. Marugan, Multi-gram scale synthesis of FR180204, J. Org. Chem. 74 (2009) 8870-8873.
28. F.X. Tavares, J.A. Boucheron, S.H. Dickerson, R.J. Griffin, F. Preugschat, S.A. Thomson, T.Y. Wang, H.-Q. Zhou, N-phenyl-4-pyrazolo[1, 5-b]pyridazin-3-ylpyrimidin-2-amines as potent and selective inhibitors of glycogen syn-thase kinase 3 with good cellular efficacy, J. Med. Chem. 47 (2004) 4716-4730.
29. M. Hayakawa, H. Kaizawa, K. Kawaguchi, N. Ishikawa, T. Koizumi, T. Ohishi, M. Yamano, M. Okada, M. Ohta, S. Tsukamoto, F.I. Raynaud, M.D. Waterfield, P. Parker, P. Workman, Synthesis and biological evaluation of imidazo [1, 2-a] pyridine derivatives as novel PI3 kinase p110a inhibitors, Bioorg. Med. Chem. 15 (2007) 403-412.
30. D. Gerard, R. Bernard, 2-Nitrodiphenylamine, Meml. Poudres 40 (1958) 225-239.
31. M. asuyoshi, N. Noriko, H. Hiroko, T. Shoji, Acid-catalyzed reactions of 3-(hydroxymethyl)-and 3-(1-hydroxyethyl)pyrazolo[1, 5-a]pyridines, J. Heterocycl. Chem. 26 (1989) 1739-1745.
32. S. Kurt, K. Fritz, K. Botho, Imidazopyridines and related ring systems. I. Syntheses of imidazopyridines. 1, Chem. Ber. 88 (1955) 1093-1102.
33. J.E. Starrett Jr., T.A. Montzka, A.R. Crosswell, R.L. Cavanagh, Synthesis and biological activity of 3-substituted imidazo[1, 2-a ]pyridines as antiulcer agents, J. Med. Chem. 32 (1989) 2204-2210.