Synthesis and antiproliferative activity of 4-substituted-piperazine-1- carbodithioate derivatives of 2,4-diaminoquinazoline

European Journal of Medicinal Chemistry

Volumn 64, Issue , 2013, Pages 401-409

  Cao, Sheng Li ^a   Han, Ying ^a   Yuan, Chong Zhen ^a   Wang, Yao ^a   Xiahou, Zhi Kai ^a   Liao, Ji ^a   Gao, Rui Ting ^a   Mao, Bei Bei ^a   Zhao, Bao Li ^a   Li, Zhong Feng ^a   Xu, Xingzhi ^a  

^a CAPITAL NORMAL UNIVERSITY   (China)

Author keywords

2,4 Diaminoquinazoline; Antiproliferative activity; DNA damage; Piperazine 1 carbodithioate; Synthesis

Indexed keywords

(2,4 DIAMINOQUINAZOLIN 6 YL)METHYL 4 (2 CHLOROPHENYL)PIPERAZINE 1 CARBODITHIOATE; (2,4 DIAMINOQUINAZOLIN 6 YL)METHYL 4 (2 FLUOROPHENYL)PIPERAZINE 1 CARBODITHIOATE; (2,4 DIAMINOQUINAZOLIN 6 YL)METHYL 4 (2 METHYLPHENYL)PIPERAZINE 1 CARBODITHIOATE; (2,4 DIAMINOQUINAZOLIN 6 YL)METHYL 4 (2,4 DIMETHYLPHENYL)PIPERAZINE 1 CARBODITHIOATE; (2,4 DIAMINOQUINAZOLIN 6 YL)METHYL 4 (3,4 DICHLOROPHENYL)PIPERAZINE 1 CARBODITHIOATE; (2,4 DIAMINOQUINAZOLIN 6 YL)METHYL 4 (4 CHLOROPHENYL)PIPERAZINE 1 CARBODITHIOATE; (2,4 DIAMINOQUINAZOLIN 6 YL)METHYL 4 (4 FLUOROPHENYL)PIPERAZINE 1 CARBODITHIOATE; (2,4 DIAMINOQUINAZOLIN 6 YL)METHYL 4 (4 HYDROXYPHENYL)PIPERAZINE 1 CARBODITHIOATE; (2,4 DIAMINOQUINAZOLIN 6 YL)METHYL 4 (4 METHOXYPHENYL)PIPERAZINE 1 CARBODITHIOATE; (2,4 DIAMINOQUINAZOLIN 6 YL)METHYL 4 (4 METHYLPHENYL)PIPERAZINE 1 CARBODITHIOATE; (2,4 DIAMINOQUINAZOLIN 6 YL)METHYL 4 BENZYLPIPERAZINE 1 CARBODITHIOATE; (2,4 DIAMINOQUINAZOLIN 6 YL)METHYL 4 CYCLOHEXYLPIPERAZINE 1 CARBODITHIOATE; (2,4 DIAMINOQUINAZOLIN 6 YL)METHYL 4 METHYLPIPERAZINE 1 CARBODITHIOATE; (2,4 DIAMINOQUINAZOLIN 6 YL)METHYL 4 PHENYLPIPERAZINE 1 CARBODITHIOATE; 2 AMINO 5 METHYLBENZONITRILE; 2,4 BIS(PIVALOYLAMINO) 6 (BROMOMETHYL)QUINAZOLINE; 2,4 BIS(PIVALOYLAMINO) 6 METHYLQUINAZOLINE; 2,4 DIAMINO 6 METHYLQUINAZOLINE; 2,4 DIAMINOQUINAZOLINE DERIVATIVE; 3 (HYDROXYIMINO) 5 METHYLINDOLIN 2 ONE; 4 SUBSTITUTED PIPERAZINE 1 CARBODITHIOATE DERIVATIVE; 6 (BROMOMETHYL) 2,4 DIAMINOQUINAZOLINE; DIHYDROFOLATE REDUCTASE; FLUOROURACIL; METHOTREXATE; PIPERAZINE DERIVATIVE; RALTITREXED; THYMIDYLATE SYNTHASE; TRIMETREXATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BREAST ADENOCARCINOMA; CANCER CELL CULTURE; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL STRAIN A549; CELL STRAIN HCT116; COLORECTAL CANCER; CONTROLLED STUDY; DNA DAMAGE; DRUG SYNTHESIS; ENZYME ACTIVITY; FEMALE; HUMAN; HUMAN CELL; IC 50; LUNG CANCER; UTERINE CERVIX CARCINOMA;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; HCT116 CELLS; HELA CELLS; HT29 CELLS; HUMANS; MCF-7 CELLS; MOLECULAR STRUCTURE; PIPERAZINES; QUINAZOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; THIOCARBAMATES;

EID: 84877254062     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.04.017     Document Type: Article

References (25)

1. A.L. Jackman, F.T. Boyle, and K.R. Harrap Tomudex (ZD1694), from concept to care, a program in rational drug discovery Invest. New Drugs 14 1996 305 316
2. D. Cunningham, J. Zalcberg, J. Maroun, R. James, S. Clarke, T.S. Maughan, M. Vincent, J. Schulz, M.G. Baron, and T. Facchini Efficacy, tolerability and management of raltitrexed (Tomudex™) monotherapy in patients with advanced colorectal cancer: a review of phase II/III trials Eur. J. Cancer 38 2002 478 486 (Pubitemid 34185386)
3. S.E. Webber, T.M. Bleckman, J. Attard, J.G. Deal, V. Katherdekar, K.M. Welsh, S. Webber, C.A. Janson, D.A. Matthews, W.W. Smith, S.T. Freer, S.R. Jordan, R.J. Bacquet, E.F. Howland, C.J.L. Booth, R.W. Ward, S.M. Hermann, J. White, C.A. Morse, J.A. Hilliard, and C.A. Bartlett Design of thymidylate synthase inhibitors using protein crystal structures: the synthesis and biological evaluation of a novel class of 5-substituted quinazolines J. Med. Chem. 36 1993 733 746 (Pubitemid 23105727)
4. S. Webber, C.A. Bartlett, T.J. Boritzki, J.A. Hilliard, E.F. Howland, A.L. Johnston, M. Kosa, S.A. Margosiak, C.A. Morse, and B.V. Shetty AG337, a novel lipophilic thymidylate synthase inhibitor: in vitro and in vivo preclinical studies Cancer Chemother. Pharmacol. 37 1996 509 517 (Pubitemid 26080147)
5. A. Gangjee, W. Li, J. Yang, and R.L. Kisliuk Design, synthesis, and biological evaluation of classical and nonclassical 2-amino-4-oxo-5-substituted- 6-methylpyrrolo[3,2-d]pyrimidines as dual thymidylate synthase and dihydrofolate reductase inhibitors J. Med. Chem. 51 2008 68 76
6. A. Gangjee, X. Lin, R.L. Kisliuk, and J.J. McGuire Synthesis of N-{4-[(2,4-diamino-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio] benzoyl}-L-glutamic acid and N-{4-[(2-Amino-4-oxo-5-methyl-4,7-dihydro-3H- pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid as dual inhibitors of dihydrofolate reductase and thymidylate synthase and as potential antitumor agents J. Med. Chem. 48 2005 7215 7222 (Pubitemid 41743635)
7. A. Gangjee, H.D. Jain, and S. Kurup Recent advances in classical and non-classical antifolates as antitumor and antiopportunistic infection agents: part I Anti-Cancer Agents Med. Chem. 7 2007 524 542 (Pubitemid 351836124)
8. A. Gangjee, H.D. Jain, and S. Kurup Recent advances in classical and non-classical antifolates as antitumor and antiopportunistic infection agents: part II Anti-Cancer Agents Med. Chem. 8 2008 205 231 (Pubitemid 351761445)
9. A. Ciccia, and S.J. Elledge The DNA damage response: making it safe to play with knives Mol. Cell. 40 2010 179 204
10. M. Pilátová, M. Šarišský, P. Kutschy, A. Miroššay, R. Mezencev, Z. Čurillová, M. Suchý, K. Monde, L. Mirossay, and J. Mojžiš Cruciferous phytoalexins: antiproliferative effects in T-Jurkat leukemic cells Leuk. Res. 29 2005 415 421 (Pubitemid 40255816)
11. P. Csomós, I. Zupkó, B. Réthy, L. Fodor, G. Falkay, and G. Bernáth Isobrassinin and its analogues: novel types of antiproliferative agents Bioorg. Med. Chem. Lett. 16 2006 6273 6276 (Pubitemid 44709904)
12. X. Hou, Z. Ge, T. Wang, W. Guo, J. Cui, T. Cheng, C. Lai, and R. Li Dithiocarbamic acid esters as anticancer agent. Part 1: 4-substituted- piperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl esters Bioorg. Med. Chem. Lett. 16 2006 4214 4219
13. M.A.-H. Zahran, T.A.-R. Salem, R.M. Samaka, H.S. Agwa, and 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
14. P. Gaspari, T. Banerjee, W.P. Malachowski, A.J. Muller, G.C. Prendergast, J. DuHadaway, S. Bennett, and A.M. Donovan Structure-activity study of brassinin derivatives as indoleamine 2,3-dioxygenase inhibitors J. Med. Chem. 49 2006 684 692 (Pubitemid 43157498)
15. S.L. Cao, Y.P. Feng, Y.Y. Jiang, S.Y. Liu, G.Y. Ding, and R.T. Li Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains Bioorg. Med. Chem. Lett. 15 2005 1915 1917
16. S.L. Cao, Y.P. Feng, X.L. Zheng, Y.Y. Jiang, M. Zhang, Y. Wang, and M. Xu Synthesis of substituted-benzylamino- and heterocyclylmethylamino- carbodithioate derivatives of 4(3H)-quinazolinone and their cytotoxic activity Arch. Pharm. 339 2006 250 254 (Pubitemid 43798340)
17. S.L. Cao, Y. Wang, L. Zhu, J. Liao, Y.W. Guo, L.L. Chen, H.Q. Liu, and 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
18. G.R. Bedford, and M.W. Partridge A convenient preparation of o-aminoaryl cyanides J. Chem. Soc. 1959 1633 1634
19. N.S.A. Zeni Preparation of o-cyanoanilines from Isatin Oximes. JP 2003064039A 2003
20. L.M. Werbel, E.F. Elslager, and L.S. Newton Antimalarial agents. Part 62. Synthesis and antimalarial activity of a series of 2,4-diamino-6-[(N- alkylanilino)methyl]quinazolines J. Heterocycl. Chem. 24 1987 345 349 (Pubitemid 17107859)
21. I.D. Goldman, S. Chattopadhyay, R. Zhao, and R. Moran The antifolates: evolution, new agents in the clinic, and how targeting delivery via specific membrane transporters is driving the development of a next generation of folate analogs Curr. Opin. Investig. Drugs 11 2010 1409 1423
22. A.P. Stankevicius, P.B. Terentiev, L.N. Janushene1, and A.B. Savickas Chem. Heterocycl. Compd. 41 2005 98 104
23. X. Xu, J.H. Lee, and D.F. Stern Microcephalin is a DNA damage response protein involved in regulation of CHK1 and BRCA1 J. Biol. Chem. 279 2004 34091 34094 (Pubitemid 39318029)
24. X. Xu, and D.F. Stern NFBD1/MDC1 regulates ionizing radiation-induced focus formation of DNA checkpoint signaling and repair factors FASEB J. 17 2003 1842 1848 (Pubitemid 37214778)
25. X. Xu, and D.F. Stern NFBD1/KIAA0170 is a chromatin-associated protein involved in DNA damage signaling pathways J. Biol. Chem. 278 2003 8795 8803 (Pubitemid 36800637) Higher Learning