Synthesis, cytotoxic activity, DNA topoisomerase-II inhibition, molecular modeling and structure-activity relationship of 9-anilinothiazolo[5,4-b]quinoline derivatives

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 9, 2009, Pages 3266-3277

  Loza Mejía, Marco A ^a   Olvera Vázquez, Susana ^a   Maldonado Hernández, Karina ^a   Guadarrama Salgado, Teresita ^a   González Sánchez, Ignacio ^a   Rodríguez Hernández, Fernando ^a   Solano, José D ^a   Rodríguez Sotres, Rogelio ^a   Lira Rocha, Alfonso ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Cytotoxic activity; DNA topoisomerase II inhibition; Molecular modeling; Structure activity relationship; Thiazolo 5,4 b quinoline

Indexed keywords

1 [3 ((2 (METHYLTHIO)THIAZOLO[5,4 B]QUINOLIN 9 YL) AMINO)PHENYL]ETHANONE; 1 [3 ((2 (METHYLTHIO)THIAZOLO[5,4 B]QUINOLIN 9 YL)AMINO)PHENYL)ETHANONE OXIME; 7 FLUORO 9 (PHENYLAMINO) 2 (METHYLTHIO) 9 ANILINOTHIAZOLO[5,4 B]QUINOLINE; 9 (PHENYLAMINO) 2 [3 (N,N DIETHYLAMINO)]PROPYLAMINOTHIAZOLO[5,4 B]QUINOLINE; 9 ANILINOTHIAZOLO[5,4 B]QUINOLINE DERIVATIVE; 9 CHLORO 2 (1 MORPHONYL)THIAZOLO[5,4 B]QUINOLINE; 9 CHLORO 2 (1 PIPERIDINYL)THIAZOLO[5,4-B]QUINOLINE; 9 CHLORO 2 [1 ((4-METHYL)PIPERAZINYL))THIAZOLO[5,4 B] QUINOLINE; 9 PHENYLAMINO 2 (1 MORPHONYL)THIAZOLO[5,4 B]QUINOLINE; 9 PHENYLAMINO 2 (1 PIPERIDINYL)THIAZOLO[5,4 B]QUINOLINE; 9 PHENYLAMINO 2 [1 ((4 METHYL)PIPERAZINYL)]THIAZOLO[5,4 B]QUINOLINE; 9 [((3 CHLORO)PHENYL)AMINO] 2 [3 (N,N DIETHYLAMINO)]PROPYLAMINOTHIAZOLO[5,4 B]QUINOLINE; 9 [((3 CYANO)PHENYL)AMINO) 2 [2 (N,N DIETHYLAMINO)]ETHYLAMINOTHIAZOLO[5,4 B]QUINOLINE; 9 [((3 CYANO)PHENYL)AMINO] 2 [3 (N,N DIETHYLAMINO)]PROPYLAMINOTHIAZOLO[5,4 B]QUINOLINE; 9 [((3 CYANO)PHENYL)AMINO] 7 FLUORO 2 (METHYLTHIO) 9 ANILINOTHIAZOLO[5,4 B]QUINOLINE; 9 [((3 ETHOXYCARBONYL)PHENYL]AMINO] 2 (METHYLTHIO) THIAZOLO[5,4 B]QUINOLINE; 9 [((3 METHOXY)PHENYL)AMINO] 2 [2 (N,N DIETHYLAMINO)]ETHYLAMINOTHIAZOLO[5,4 B]QUINOLINE; 9 [((3 METHOXY)PHENYL)AMINO] 7 FLUORO 2 (METHYLTHIO) 9 ANILINOTHIAZOLO[5,4 B]QUINOLINE; 9 [((4 CHLORO)PHENYL)AMINO] 2 [2 (N,N DIETHYLAMINO)]ETHYLAMINOTHIAZOLO[5,4 B]QUINOLINE; 9 [((4 CHLORO)PHENYL)AMINO] 2 [3 (N,N DIETHYLAMINO)]PROPYLAMINOTHIAZOLO[5,4-B]QUINOLINE; 9 [((4 CYANO)PHENYL)AMINO] 2 [2 (N,N DIETHYLAMINO)]ETHYLAMINOTHIAZOLO[5,4 B]QUINOLINE; 9 [((4 CYANO)PHENYL)AMINO] 2 [3 (N,N DIETHYLAMINO)]PROPYLAMINOTHIAZOLO[5,4 B]QUINOLINE; 9 [((4 CYANO)PHENYL)AMINO] 7 FLUORO 2 (METHYLTHIO) 9 ANILINOTHIAZOLO[5,4 B]QUINOLINE; 9 [((4 METHOXY)PHENYL)AMINO] 2 [2 (N,N DIETHYLAMINO)]ETHYLAMINOTHIAZOLO[5,4 B]QUINOLINE; 9 [((4 METHOXY)PHENYL)AMINO] 7 FLUORO 2 (METHYLTHIO) 9 ANILINOTHIAZOLO[5,4 B]QUINOLINE; 9 [{(3 CHLORO)PHENYL)AMINO] 2 [2 (N,N DIETHYLAMINO)]ETHYLAMINOTHIAZOLO[5,4-B]QUINOLINE; ANTINEOPLASTIC AGENT; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CELL ACTIVITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; HYDROPHOBICITY; IN VITRO STUDY; MOLECULAR MODEL; STRUCTURE ACTIVITY RELATION;

ANILINE COMPOUNDS; DNA; DNA TOPOISOMERASES, TYPE II; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; HELA CELLS; HUMANS; K562 CELLS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUINOLINES; THIAZOLES; TOPOISOMERASE II INHIBITORS;

EID: 65349127031     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.03.052     Document Type: Article

References (25)

1. Capranico G., and Binaschi M. Biochim. Biophys. Acta 1400 (1998) 185
2. Osheroff N., and Burden B. Biochim. Biophys. Acta 1400 (1998) 129
3. Demecunynck H., Charmantray F., and Martelli A. Curr. Pharm. Des. 7 (2001) 1703
4. Denny W.A. In: Foye W.O. (Ed). Cancer Chemotherapeutic Agents (1995), American Chemical Society, Washington, DC 218-239
5. Arlin Z.A. Cancer Invest. 7 (1989) 607
6. Su T.S., Chou T., Kim J.Y., Huang J., Ciszewska G., Ren W., Otter G., Sirotnak F., and Watanabe K. J. Med. Chem. 38 (1995) 3226
7. Rodríguez-Loaiza P., Quintero A., Rodríguez-Sotres R., Solano J.D., and Lira-Rocha A. Eur. J. Med. Chem. 39 (2004) 5
8. Loza-Mejía M.A., Maldonado-Hernández K., Rodríguez-Hernández F., Rodríguez-Sotres R., González-Sánchez I., Solano J.D., and Lira-Rocha A. Bioorg. Med. Chem. 16 (2008) 1142
9. Chen Y., Chen I., Lu C., Tzeng C., Tsao L., and Wang J. Bioorg. Med. Chem. 12 (2004) 387
10. Chen Y., Chen I., Wang T., Han C., and Tzeng C. Eur. J. Med. Chem. 40 (2005) 928
11. Bontemps-Gracz M.M., Kupiec A., Antonini I., and Borowski E. Acta Biochim. Pol. 49 (2002) 87
12. Stefanska B., Bontemps-Gracz M.M., Antonini I., Martelli S., Arciemiuk M., Piwkowska A., Rogacka D., and Borowski E. Bioorg. Med. Chem. 13 (2005) 1969
13. Alvarez-Ibarra C., Fernández-Granda R., Quiroga M.L., Carbonell A., Cárdenas F., and Giralt E. J. Med. Chem. 40 (1997) 668
14. Moro S., Beretta G., Dal Ben D., Nitiss J., Palumbo M., and Capranico G. Biochemistry 43 (2004) 7503
15. Kingma P.S., and Osheroff N. Biochim. Biophys. Acta 1400 (1998) 195
16. spartan version 5.0, Wavefunction Inc. 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612, USA.
17. Reha D., Kabelac M., Ryjacek F., Sponer J., Sponer J., Elstner M., Suhai S., and Pavel Hobza P. J. Am. Chem. Soc. 124 (2002) 3366
18. Antonini I., Polucci P., Jenkins T.C., Kelland L.R., Menta E., Pescalli N., Stefanska B., Mazerski J., and Martelli S. J. Med. Chem. 40 (1997) 3749
19. Dantas S.O., Lavarda F.C., Galvão D.S., and Laks B. J. Mol. Struct. (THEOCHEM) 253 (1992) 319
20. Barone P.M.V.B., Dantas S.O., and Galvão D.S. J. Mol. Struct. (THEOCHEM) 465 (1999) 219
21. Braga S.F., de Melo L.C., and Barone P.M.V.B. J. Mol. Struct. (THEOCHEM) 710 (2004) 51
22. Clark D.E. J. Pharm. Sci. 88 (1999) 807
23. Quintero A., Pelcastre A., Dolores J., Guzmán A., and Díaz E. J. Pharm. Pharmaceut. Sci. 2 (1999) 108
24. Haldane A., and Sullivan D.M. DNA Topoisomerase II-Catalyzed DNA Decatenation. In: Osheroff N., and Biornst N.A. (Eds). Methods in Molecular Biology v. 95. DNA topoisomerase protocols, Part II: Enzymology and drugs (2001), Humana Press, Totowa NJ 13-23
25. Abramoff M.D., Magelhaes P.J., and Ram S.J. Biophoton. Int. 11 (2004) 36