Novel cyano- and amidino-substituted derivatives of styryl-2-benzimidazoles and benzimidazo[1,2-a]quinolines. Synthesis, photochemical synthesis, DNA binding, and antitumor evaluation, part 3

Journal of Medicinal Chemistry

Volumn 50, Issue 23, 2007, Pages 5696-5711

  Hranjec, Marijana ^a   Kralj, Marijeta ^b   Piantanida, Ivo ^b   Sedić, Mirela ^b   Šuman, Lidija ^b   Pavelić, Krešimir ^b   Karminski Zamola, Grace ^a  

^a UNIVERSITY OF ZAGREB   (Croatia)

^b RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

[No Author keywords available]

Indexed keywords

2 [2 STYRYL 3H BENZIMIDAZOL 5(6) YL] 4,5 DIHYDRO 3H IMIDAZOL 1 YL; 2 BENZIMIDAZO[1,2 A]QUINOLIN 10(9) YL 4,5 DIHYDRO 3H IMIDAZOL 1 YL; AMIDINE; BENZIMIDAZO[1,2 A]QUINOLINE 9 CARBONITRILE; BENZIMIDAZOLE DERIVATIVE; CHLORINE DERIVATIVE; DNA TOPOISOMERASE (ATP HYDROLYSING); DOUBLE STRANDED DNA; DOXORUBICIN; ETOPOSIDE; MERBARONE; MORPHOLINE DERIVATIVE; N MORPHOLIN 4 YLBENZIMIDAZO[1,2 A]QUINOLINE 9(10) CARBOXAMIDINE; NITRILE; QUINOLINE DERIVATIVE; RAZOXANE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CARCINOMA CELL; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CIRCULAR DICHROISM; CONTROLLED STUDY; CYCLIZATION; DENATURATION; DRUG DNA BINDING; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; FLUORESCENCE SPECTROSCOPY; HALOGENATION; HUMAN; HUMAN CELL; INTERCALATION COMPLEX; MITOSIS; PHOTOCHEMISTRY; POLYMERIZATION; REACTION ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

AMIDINES; ANTINEOPLASTIC AGENTS; BENZIMIDAZOLES; CELL CYCLE; CIRCULAR DICHROISM; CYCLIZATION; DNA; DNA TOPOISOMERASES, TYPE II; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; NITRILES; PHOTOCHEMISTRY; QUINOLINES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; STYRENES;

EID: 36148947863     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070876h     Document Type: Article

References (48)

1. Bailly, C. Topoisomerase I Poisons and Suppressors as Anticancer Drugs. Curr. Med. Chem. 2000, 7, 39-58.
2. Demeunynck, M.; Bailly, C.; Wilson, W. D. DNA and RNA Binders; Wiley-VCH: Weinheim, 2002.
3. Silverman, R. B. The Organic Chemistry of Drug Design and Drug Action, second ed.; Elsevier Academic Press: New York, 2004.
4. Yang, X. L.; Wang, A. H.-J. Structural studies of atom-specific anticancer drugs acting on DNA. Pharmacol. Ther. 1999, 83, 181-215.
5. Pastor, J.; Siro, J. G.; García-Navío, J. L.; Vaquero, J. J.; Alvarez-Builla, J.; Gago, F.; Pascual-Teresa, B.; Pastor, M.; Rrodrigo, M. M. Azino-fused benzimidazolium salts as DNA intercalating agents. J. Org. Chem. 1997, 62, 5476-5483.
6. Martínez, V.; Burgos, V.; Alvarez-Builla, J.; Fernández, G; Domingo, A.; Garcia-Nieto, R.; Gago, F.; Manzanares, I.; Cuevas, C.; Vaquero, J. J. Benzo[f]azino[2,1-a]phthalazinium cations: Novel DNA intercalating chromophores with antiproliferative activity. J. Med. Chem. 2004, 47, 1136-1148.
7. Katritzky, A. R.; Tymoshenko, D. O.; Monteux, D.; Vvedensky, V.; Nikonov, G.; Cooper, C. B.; Deshpande, M. A new three-carbon synthon for efficient synthesis of benzannelated and 1-(2-arylethenyl)-heterocycles. J. Org. Chem. 2000, 65, 8059-8062.
8. El-Hawash, S. A. M.; Badawey, E.; Kappe, T. Benzimidazole-condensed ring systems. XII. Synthesis and anticancer evaluation of certain pyrido[1,2-a]benzimidazole derivatives. Pharmazie 1999, 54, 341-346.
9. Demirayak, S.; Abu Mohsen, U.; Cagri Karaburun, A. Synthesis and anticancer and anti-HIV testing of some pyrazino[1,2-a]benzimidazole derivatives. Eur. J. Med. Chem. 2002, 37(3), 255-260.
10. Kumar, D.; Jacob, M. R.; Reynolds, M. B.; Kerwin, S. M. Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1. Bioorg. Med. Chem. 2002, 10(12), 3997-4004.
11. He, Y.; Yang, J.; Baogen, W.; Risen, L.; Swayze, E. E. Synthesis and biological evaluations of novel benzimidazoles potential anti-bacterial agents. Bioorg. Med. Chem. Lett. 2004, 14, 1217-1220.
12. Ismail, M. A.; Brun, R.; Wenzler, T.; Tanious, F. A.; Wilson, W. D.; Boykin, D. W. Dicationic biphenyl benzimidazole derivatives as antiprotozoal agents. Bioorg. Med. Chem. 2004, 12 (20), 5405-5413.
13. Göker, H.; Ozden, S.; YiS.; Boykin, D. W. Synthesis and potent antibacterial activity against MRSA of some novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5-carboxamidines. Eur. J. Med. Chem. 2005, 40, 1062-1069.
14. Brana, M. F.; Castellano, J. M.; Keilhauer, G.; Machuca, A.; Martín, Y.; Redondo, C.; Schlick, E.; Walker, N. Benzimidazo[1,2- c]-quinazolines: A new class of antitumor compounds. Anti-Cancer Drug Des. 1994, 9, 527-538.
15. Deady, L. W.; Rodemann, T.; Finlay, G. J.; Baguley, B. C.; Denny, W. A. Synthesis and cytotoxic activity of carboxamide derivatives of benzimidazo[2,1-a]isoquinoline and pyrido[3′,2′:4,5] imidazo[2,1-a]isoquinoline. Anti-Cancer Drug Des. 2000, 15, 339-346.
16. Weinkauf, R. L.; Chen, A. Y.; Yu, C.; Liu, L.; Barrows, L.; LaVoie, E. J. Antineoplastic activity of benzimidazo[1,2-b]isoquinolines, indolo[2,3-b]quinolines, and pyridocarbazoles. Bioorg. Med. Chem. 1994, 2(8), 781-786.
17. Cox, O.; Jackson, H.; Vargas, V. A.; Bàez, A.; Colón, J. I.; Gonzalez B. C.; De León, M. Synthesis and biological activity of benzothiazolo-and benzoxazolo[3,2-a]quinolinium salts. J. Med. Chem. 1982, 25, 1378-1381.
18. Muir, M. M.; Cox, O.; Rivera, L. A. Synthesis and characterization of new platinum(II) complexes containing thiazole and imidazole donors III. Dichloro(styrylbenzimidazole) platinum(II) complexes. Inorg. Chim. Acta. 1992, 191, 131-139.
19. Alegria, A. A.; Cox, O.; Santiago, V.; Colon, M.; Reyes, Z.; Zayas, L.; Rivera L. A.; Dumas, J. A. Reductive activation of benzazolo-[3,2-a] quinolinium chlorides. Free Radical Biol. Med. 1993, 15, 49-56.
20. Vivas-Mejía, P.; Rodríguez-Cabán, J. L.; Díaz-Velázquez, M.; Hernández-Pérez, M. G.; Cox, O.; Gonzalez, F. A. DNA binding-independent anti-proliferative action of benzazolo[3,2-a]quinolinium DNA intercalators. Mol. Cell. Biochem. 1997, 177, 69-77.
21. Vivas-Mejía, P.; Cox, O.; Gonzalez, F. A. Inhibition of human topoisomerase II by anti-neoplastic benzazolo[3,2-α]quinolinium chlorides. Mol. Cell. Biochem. 1998, 178, 203-212.
22. Morgan, G.; Stewart, J. Pyrido[1′:2′:1:2]benziminazoles and allied compounds (cyclic 1:3-diazalines). J. Chem. Soc. 1938, 1292-1305.
23. Cooper, G.; Irwin, W. J. Photocyclisation of 1-styrylimidazoles. A novel route to N-bridgehead compounds. J. Chem. Soc., Perkin Trans. 1 1975, 75-80.
24. Venkatesh, C.; Sundaram, G. S. M.; Ila, H.; Junjappa, H. Palladium-catalyzed intramolecular N-arylation of heteroarenes: A novel and efficient route tobenzimidazo[1,2-a]quinolines. J. Org. Chem. 2006, 71, 1280-1283.
25. Shenoy, V. U.; Seshardi, S. Synthesis of benzimidazo-[1,2-a]- quinolines: Fluorescent disperse dyes. Dyes and pigments. 1989, 11, 137-145.
26. Guether, D. Benzimidazo-[1,2-a]-quinolines. U.S. Patent 4,124,589, 1978.
27. Guether, D.; Erckel, R.; Fruhbeis, H. Benzimidazo-[1,2-a]- quinolines. U.S. Patent 4,219,651, 1980.
28. Hranjec, M.; Kralj, M.; Pavelić, K.; Karminski-Zamola, G. Hrvatski Patentni glasnik. Patent Appl. HP 20050806A, 2005.
29. Hranjec, M.; Starčević, K.; Zamola, B.; Muatk, S.; Karminski-Zamola, G. New amidino-benzimidazolyl derivatives of tylosin and desmycosin. J. Antibiot. 2002, 55(3), 308-314.
30. Hranjec, M.; Grdiša, M.; Pavelić, K.; Boykin, D. W.; Karminski-Zamola, G. Synthesis and antitumor evaluation of some new substituted amidino-benzimidazolyl-furyl-phenyl-acrylates and naphtho[2,1-b]furan- carboxylates. Il Farmaco. 2003, 58, 1319-1324.
31. I. Starčević, K.; Boykin, D. W.; Karminski-Zamola, G. New amidino-substituted benzimidazolyl furyl-thienyl-acrylates and benzo-thienofurans: Synthesis and photochemical synthesis. Heterocycl. Commun. 2002, 8 (3), 221-226.
32. Czarny, A.; Wilson, W. D.; Boykin, D. W. Synthesis of mono-cationic and dicationic analogs of Hoechst 33258. J. Heterocycl. Chem. 1996, 33, 1393-1397.
33. Oszczapowicz, J. In The chemistry of Amidines and Imidates; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: London, New York, 1991; Vol. 2, p 623.
34. Fairley, T. A.; Tidwell, R. R.; Donkor, I.; Naiman, N. A.; Ohemeng, K. A.; Lombardy, R. J.; Bentley, J. A.; Cory, M. Structure, DNA minor-groove binding and base-pair specificity of alkyl-linked and aryl-linked bis(amidinobenzimidazoles) and bis(amidinoindoles). J. Med. Chem. 1993, 36, 1746-1753.
35. Ramaiah, K.; Dubey, P. K.; Esvara Rao, D.; Ramanatham, J.; Kumar, R. Synthesis and spectral properties of variety of 2-styrylbenzimidazoles. Ind. J. Chem. 2000, 39B, 904-914.
36. (a) Scatchard, G. The attractions of proteins for small molecules and ions. Ann. N.Y. Acad. Sci. 1949, 51, 660.
37. (b) McGhee, J. D.; von Hippel, P. H. Erratum: Theoretical aspects of DNA-protein interactions: Co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice. J. Mol. Biol. 1976, 103, 679.
38. Berova, N.; Nakanishi, K.; Woody, R. W. Circular dichroism principles and applications, 2nd ed.; Wiley-VCH: New York, 2000.
39. Eriksson, M.; Norden, B. Methods Enzymol. 2001, 340, 68-70, Table I.
40. Jarak, I.; Kralj, M.; Šuman, L.; Pavlović, G.; Dogan, J.; Piantanida, I.; Žinić, M.; Pavelić, K.; Karminski-Zamola, G. Novel cyano- and N-isopropylamidino-substituted derivatives of benzo[b]thiophene-2-carboxanilides and benzo[b]thieno[2,3-c] quinolones: Synthesis, photochemical synthesis, crystal structure determination and antitumor evaluation. Part 2. J. Med. Chem. 2005, 48, 2346-2360.
41. Jarak, I.; Kralj, M.; Piantanida, I.; Šuman, L.; Žinić, M.; Pavelić K.; Karminski-Zamola, G. Novel cyano- and amidino-substituted derivatives of thieno[2,3-b]- and thieno[3,2-b]thiophene-2-carboxanilides and thieno[3′,2′:4,5] thieno- and thieno[2′,3′:4,5]thieno[2,3-c]quinolones: Synthesis, photochemical synthesis, DNA binding and antitumor evaluation. Bioorg. Med. Chem. 2006, 14, 2859-2868.
42. Starčević, K.; Kralj, M.; Piantanida, I.; Šuman, L.; Pavelić, K.; Karminski-Zamola, G. Synthesis, photochemical synthesis, DNA binding, and antitumor evaluation of novel cyano- and amidino-substituted derivatives of naphtho-furans, naphtho-thiophenes, thieno-benzofurans, benzo-dithiophenes, and their acyclic precursors. Eur. J. Med. Chem. 2006, 41, 925-937.
43. Khélifa, T.; Beck, W. T. Merbarone, a catalytic inhibitor of DNA topoisomerase II, induces apoptosis in CEM cells through activation of ICE/CED-3-like protease. Mol. Pharmacol. 1999, 55, 548-556.
44. Wang, L.; Eastmond, D. A. Catalytic inhibitors of topoisomerase II are DNA-damaging agents: Induction of chromosomal damage by merbarone and ICRF-187. Environ. Mol. Mutagen. 2002, 39, 348-356.
45. Anderson, H.; Roberge, M. Topoisomerase II inhibitors affect entry into mitosis and chromosome condensation in BHK cells. Cell Growth Differ. 1996, 7, 83-90.
46. (a) Chaires, J. B.; Dattagupta, N.; Crothers, D. M. Studies on interaction of anthracycline antibiotics and deoxyribonucleic acid: equilibrium binding studies on interaction of daunomycin with deoxyribonucleic acid. Biochemistry 1982, 21, 3933.
47. (b) Palm, B. S.; Piantanida, I.; Žinić, M.; Schneider, H. J. The interaction of new 4,9-diazapyrenium compounds with double stranded nucleic acids. J. Chem. Soc., Perkin Trans. 2 2000, 385.
48. Boyd, M. R.; Kenneth, D. P. Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen. Drug. Dev. Res. 1995, 34, 91-109.