Synthesis and anticancer activity of some novel 2-phenazinamine derivatives

European Journal of Medicinal Chemistry

Volumn 69, Issue , 2013, Pages 1-9

  Gao, Xiaochun ^a   Lu, Yuanyuan ^a   Fang, Lei ^b   Fang, Xubin ^b   Xing, Yingying ^a   Gou, Shaohua ^b   Xi, Tao ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b SOUTHEAST UNIVERSITY   (China)

Author keywords

2 Phenazinamine derivatives; Anticancer activity; Apoptosis; MTT assay

Indexed keywords

1,1 DIMETHYL 3 (PHENAZIN 2 YL)UREA; 2 CHLORO N (PHENAZIN 2 YL)BENZAMIDE; 2 METHYL N (PHENAZIN 2 YL)BENZAMIDE; 3 CHLORO N (PHENAZIN 2 YL)BENZAMIDE; 3 CYCLOPENTYL N (PHENAZIN 2 YL)PROPANAMIDE; 3 METHYL N (PHENAZIN 2 YL)BENZAMIDE; 4 METHOXY N (PHENAZIN 2 YL)BENZAMIDE; 4 METHYL N (PHENAZIN 2 YL)BENZAMIDE; ANTINEOPLASTIC AGENT; CISPLATIN; ETHYL PHENAZIN 2 YLCARBAMATE; N (PHENAAZIN 2 YL)CYCLOHEXANECARBOXAMIDE; N (PHENAZIN 2 YL) 1 NAPHTHAMIDE; N (PHENAZIN 2 YL) 2 (THIOPHEN 2 YL)ACETAMIDE; N (PHENAZIN 2 YL) 2 PHENYLACETAMIDE; N (PHENAZIN 2 YL)ACETAMIDE; N (PHENAZIN 2 YL)BENZAMIDE; N (PHENAZIN 2 YL)BENZENESULFONAMIDE; N (PHENAZIN 2 YL)BUTYRAMIDE; N (PHENAZIN 2 YL)FURAN 2 CARBOXAMIDE; N (PHENAZIN 2 YL)PROPANAMIDE; N (PHENAZIN 2 YL)PROPIONAMIDE; N (PHENAZIN 2 YL)THIOPHENE 2 CARBOXAMIDE; PHENAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST ADENOCARCINOMA; CELL STRAIN HCT116; CELL STRAIN HEPG2; CELL STRAIN MCF 7; CHRONIC MYELOID LEUKEMIA; COLORECTAL CARCINOMA; CRYSTALLIZATION; DRUG CYTOTOXICITY; DRUG SYNTHESIS; ELECTROPHILICITY; EMBRYO; FLOW CYTOMETRY; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IC 50; IN VITRO STUDY; LEUKEMIA CELL LINE; LIVER CELL CARCINOMA; MELTING POINT; MOLECULAR WEIGHT; NUCLEOPHILICITY; STOMACH CARCINOMA;

2-PHENAZINAMINE DERIVATIVES; ANTICANCER ACTIVITY; APOPTOSIS; MTT ASSAY;

ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; CELL SURVIVAL; CELLS, CULTURED; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HCT116 CELLS; HEK293 CELLS; HEP G2 CELLS; HUMANS; K562 CELLS; MCF-7 CELLS; MOLECULAR STRUCTURE; PHENAZINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84884494013     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.07.017     Document Type: Article

References (37)

1. J.R. Seffrin, D. Hill, W. Burkart, I. Magrath, R.A. Badwe, T. Ngoma, A. Mohar, and N. Grey It is time to include cancer and other noncommunicable diseases in the millennium development goals CA Cancer J. Clin. 59 2009 282 284
2. A. Jemal, R. Siegel, E. Ward, Y.P. Hao, J.Q. Xu, and M.J. Thun Cancer statistics, 2009 CA Cancer J. Clin. 59 2009 225 249
3. B.D. Smith, G.L. Smith, A. Hurria, G.N. Hortobagyi, and T.A. Buchholz Future of cancer incidence in the United States: burdens upon an aging, changing nation J. Clin. Oncol. 27 2009 2758 2765
4. Y.L. Chen, S.Z. Lin, J.Y. Chang, Y.L. Cheng, N.M. Tsai, S.P. Chen, W.L. Chang, and H.J. Harn In vitro and in vivo studies of a novel potential anticancer agent of isochaihulactone on human lung cancer A549 cells Biochem. Pharmacol. 72 2006 308 319
5. J.B. Laursen, and J. Nielsen Phenazine natural products: bio-synthesis, synthetic analogues, and biological activity Chem. Rev. 104 2004 1663 1685
6. H.J. Abken, M. Tietze, J. Brodersen, S. Bäumer, U. Beifuss, and U. Deppenmeier Isolation and characterization of methanophenazine and function of phenazines in membrane-bound electron transport of Methanosarcina mazei Gö1 J. Bacteriol. 180 1998 2027 2032 (Pubitemid 28212686)
7. M.E. Makgatho, R. Anderson, J.F. O'Sullivan, T.J. Egan, J.A. Freese, N. Cornelius, and C.E.J. van Rensburg Tetramethylpiperidine-substituted phenazines as novel anti-plasmodial agents Drug Dev. Res. 50 2000 195 202
8. V.F. de Andrade-Neto, M.O.F. Goulart, J.F. da Silva Filho, M.J. da Silva, M.d.C.F.R. Pinto, A.V. Pinto, M.G. Zalis, L.H. Carvalho, and A.U. Krettli Antimalarial activity of phenazines from lapachol, β-lapachone and its derivatives against plasmodium falciparum in vitro and plasmodium berghei in vivo Bioorg. Med. Chem. Lett. 14 2004 1145 1149 (Pubitemid 38229844)
9. H. Hussain, S. Specht, S.R. Sarite, M. Saeftel, A. Hoerauf, B. Schulz, and K. Krohn A new class of phenazines with activity against a chloroquine resistant Plasmodium falciparum strain and antimicrobial activity J. Med. Chem. 54 2011 4913 4917
10. C. Neves-Pinto, V.R.S. Malta, M.d.C.F.R. Pinto, R.H.A. Santos, S.L. de Castro, and A.V. Pinto A trypanocidal phenazine derived from β-lapachone J. Med. Chem. 45 2002 2112 2115
11. W. Wang, P. Préville, N. Morin, S. Mounir, W. Cai, and M. Arshad Siddiqui Hepatitis C viral IRES inhibition by phenazine and phenazine-like molecules Bioorg. Med. Chem. Lett. 10 2000 1151 1154 (Pubitemid 30345079)
12. G.W. Rewcastle, W.A. Denny, and B.C. Baguley Potential antitumor agents. 51. Synthesis and antitumor activity of substituted phenazine-1-carboxamides J. Med. Chem. 30 1987 843 851 (Pubitemid 17119530)
13. N. Imamura, M. Nishijima, T. Takadera, K. Adachi, M. Sakai, and H. Sano A new anticancer antibiotics pelagiomicins, produced by a new marine bacterium Pelagiobacter variabilis J. Antibiot. 50 1997 8 12 (Pubitemid 27078052)
14. M.S. Abdelfattah, T. Kazufumi, and M. Ishibashi Isolation and structure elucidation of izuminosides A-C: a rare phenazine glycosides from Streptomyces sp. IFM 11260 J. Antibiot. 64 2011 271 275
15. M.S. Abdelfattah, T. Kazufumi, and M. Ishibashi New pyranonaphthoquinones and a phenazine alkaloid isolated from Streptomyces sp. IFM 11307 with TRAIL resistance-overcoming activity J. Antibiot. 64 2011 729 734
16. K. Shinya, S. Shimizu, T. Kunigami, K. Furihata, and H. Seto A new neuronal cell protecting substance, lavanduquinocin, produced by Streptomyces viridochromogenes J. Antibiot. 48 1995 574 578
17. K. Shinya, S. Shimizu, T. Kunigami, K. Furihata, Y. Hayakawa, and H. Seto Novel neuronal cell protecting substances, aestivophoenins A and B, produced by Streptomyces purpeofuscus J. Antibiot. 48 1995 1378 1381
18. W.G. Kim, I.J. Ryoo, B.S. Yun, K. Shin-ya, H. Seto, and I.D. Yoo New diphenazines with neuronal cell protecting activity, phenazostatins A and B, produced by Streptomyces sp. J. Antibiot. 50 1997 715 721 (Pubitemid 27462596)
19. T. Kunigami, K. Shin-ya, K. Furihata, K. Furihata, Y. Hayakawa, and H. Seto A novel neuronal cell protecting substance, aestivophoenin C, produced by Streptomyces purpeofuscus J. Antibiot. 51 1998 880 882 (Pubitemid 28461727)
20. J.R. Kerr, G.W. Taylor, A. Rutman, N. Hoiby, P.J. Cole, and R. Wilson Pseudomonas aeruginosa pyocyanin and 1-hydroxyphenazine inhibit fungal growth J. Clin. Pathol. 52 1999 385 387 (Pubitemid 29200034)
21. S. Wang, W. Miller, J. Milton, N. Vicker, A. Stewart, P. Charlton, P. Mistry, D. Hardicka, and W.A. Dennyc Structure-activity relationships for analogues of the phenazine-based dual topoisomerase I/II inhibitor XR11576 Bioorg. Med. Chem. Lett. 12 2002 415 418 (Pubitemid 34113916)
22. L.S. Pierson III, and E.A. Pierson Metabolism and function of phenazines in bacteria: impacts on the behavior of bacteria in the environment and biotechnological processes Appl. Microbiol. Biotechnol. 86 2010 1659 1670
23. D. Wu, H. Chang, Y. Wang, and M. Xin Isolation, structure determination and antibacterial activities of succinamide conjugate diacid from Acinetobacter sp. BJ-L Microbiol. Res. 166 2011 155 160
24. X. Gao, Y. Lu, Y. Xing, Y. Ma, J. Lu, W. Bao, Y. Wang, and T. Xi A novel anticancer and antifungus phenazine derivative from a marine actinomycete BM-17 Microbiol. Res. 167 2012 616 622
25. N.P. Loveless, and K.C. Brown Rates of formation of some phenazines by cyclization of di-and monoimines of N-(2-aminophenyl)-p-benzoquinone J. Org. Chem. 46 1981 1182 1185
26. M.Z. Wang, H. Xu, S.J. Yu, Q. Feng, S.H. Wang, and Z.M. Li Synthesis and fungicidal activity of novel aminophenazine-1-carboxylate derivatives J. Agric. Food Chem. 58 2010 3651 3660
27. A.A. Wilson, A. Garcia, S. Houle, O. Sadovski, and N. Vasdev Synthesis and application of isocyanates radiolabeled with carbon-11 Chem. Eur. J. 17 2011 259 264
28. H. Zhang, Q. Cai, and D. Ma Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles J. Org. Chem. 70 2005 5164 5173 (Pubitemid 40863921)
29. D. Ma, and Q. Cai Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles Acc. Chem. Res. 41 2008 1450 1460
30. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 65 1983 55 63 (Pubitemid 14203433)
31. R. Miri, R. Motamedi, M.R. Rezaei, O. Firuzi, A. Javidnia, and A. Shafiee Design, synthesis and evaluation of cytotoxicity of novel chromeno[4,3-b] quinoline derivatives Arch. Pharm. 344 2011 111 118
32. W.K. Ng, L.S. Yazan, and M. Ismail Thymoquinone from Nigella sativa was more potent than cisplatin in eliminating of SiHa cells via apoptosis with down-regulation of Bcl-2 protein Toxicol. In Vitro 25 2011 1392 1398
33. E. Moreno, D. Plano, I. Lamberto, M. Font, I. Encío, J.A. Palop, and C. Sanmartín Sulfur and selenium derivatives of quinazoline and pyrido[2,3-d]pyrimidine: synthesis and study of their potential cytotoxic activity in vitro Eur. J. Med. Chem. 47 2012 283 298
34. M. Azizmohammadi, M. Khoobi, A. Ramazani, S. Emami, A. Zarrin, O. Firuzi, R. Miri, and A. Shafiee 2H-Chromene derivatives bearing thiazolidine-2,4-dione, rhodanine or hydantoin moieties as potential anticancer agents Eur. J. Med. Chem. 59 2013 15 22
35. A. Cimmino, A. Evidente, V. Mathieu, A. Andolfi, F. Lefranc, A. Kornienko, and R. Kiss Phenazines and cancer Nat. Prod. Rep. 29 2012 487 501
36. A.M. Montana, F.J. Bernal, J. Lorenzo, C. Farnos, C. Batalla, M.J. Prieto, V. Moreno, F.X. Aviles, J.M. Mesas, and M.T. Alegre Synthesis, characterization and antiproliferative studies of the enantiomers of cis-[(1,2-camphordiamine) dichloro]platinum(II) complexes Bioorg. Med. Chem. 16 2008 1721 1737 (Pubitemid 351226591)
37. A. Krishan Rapid flow cytofluorometric analysis of mammalian cell cycle by propidium iodide staining J. Cell Biol. 66 1975 188 193