A QSAR study and molecular design of benzothiazole derivatives as potent anticancer agents

Science in China, Series B: Chemistry

Volumn 51, Issue 2, 2008, Pages 111-119

  Chen, Jincan ^a   Qian, Li ^a   Shen, Yong ^a   Chen, Lanmei ^a   Zheng, Kangcheng ^a  

^a SUN YAT SEN UNIVERSITY   (China)

Author keywords

Anticancer activity; Benzothiazole derivative; DFT; Polarity interference; QSAR

Indexed keywords

CYTOTOXICITY; DENSITY FUNCTIONAL THEORY; DERIVATIVES; MOLECULAR DYNAMICS; REGRESSION ANALYSIS;

BENZOTHIAZOLE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP (QSAR); STERIC PARAMETER;

ONCOLOGY;

EID: 38349165553     PISSN: 10069291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-007-0107-8     Document Type: Article

References (33)

1. Gibbs J B, Mechanism-based target identification and drug discovery in cancer research. Science, 2000, 287: 1969-1973
2. Hayakawa I, Shioya R, Agatsuma T, Furukawa H, Naruto S, Sugano Y. 4-Hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as potent anti-tumor agents. Bioorg Med Chem Lett, 2004, 14: 455-458
3. Hayakawa I, Shioya R, Agatsuma T, Furukawa H, Sugano Y. Thienopyridine and benzofuran derivatives as potent anti-tumor agents possessing different structure-activity relationships. Bioorg Med Chem Lett, 2004, 14: 3411-3414
4. Hayakawa I, Shioya R, Agatsuma T, Sugano Y. Synthesis and evaluation of 3-methyl-4-oxo-6-phenyl-4, 5, 6, 7-tetrahydrobenzofuran-2-carboxylic acid ethyl ester derivatives as potent antitumor agents. Chem Pharm Bull, 2005, 53(6): 638-640
5. Yoshida M, Hayakawa I, Hayashi N, Agatsuma T, Oda Y, Tanzawa F, Iwasaki S, Koyama K, Furukawa H, Kurakatad S, Sugano Y. Synthesis and biological evaluation of benzothiazole derivatives as potent antitumor agents. Bioorg Med Chem Lett, 2005, 15: 3328-3332
6. Santos-Filho O A, Hopfinger A J. A search for sources of drug resistance by the 4D-QSAR analysis of a set of antimalarial dihydrofolate reductase inhibitors. J Comput Aided Mol Des, 2001, 15: 1-12
7. Nanbo A, Nanbo T. Mechanistic study on n-demethylation catalyzed with P450 by quantitative structure activity relationship using electronic properties of 4-substituted N,N-dimethylaniline. Quant Struct Act Relat, 2002, 21: 613-616
8. Wang X D, Lin Z F, Yin D Q, Liu S S, Wang L S. 2D/3D-QSAR comparative study on mutagenicity of nitroaromatics. Sci China Ser B-Chem, 2005, 48(3): 246-252
9. Karelson M, Lobanov V S. Quantum-chemical descriptors in QSAR/QSPR studies. Chem Rev, 1996, 96: 1027-1044
10. Zhang L, Wan J, Yang G F. A DFT-based QSARs study of protoporphyrinogen oxidase inhibitors: Phenyl triazolinones. Bioorg Med Chem, 2004, 12: 6183-6191
11. Wan J, Zhang L, Yang G F. Quantitative structure-activity relationship for phenyl triazolinones of protoporphyrinogen oxidase inhibitors: a density functional theory study. J Comput Chem, 2004, 25: 1827-1832
12. Wan J, Zhang, L, Yang G F, Zhan C G. Quantitative structure-activity relationship for cyclic imide derivatives of protoporphyrinogen oxidase inhibitors: a study of quantum chemical descriptors from density functional theory. J Chem Inf Comp Sci, 2004, 44: 2099-2105
13. Chen J C, Qian L, Wu W J, Chen L M, Zheng K C. A QSAR study of substituted benzo[a]phenazines as potential anticancer agents. J Mol Struct (Theochem), 2005, 756: 167-172
14. 2+ with DFT method. J Phys Chem A, 2001, 105: 10899-10905
15. Becke A D. A new mixing of Hartree-Fock and local density-functional theories. J Chem Phys, 1993, 98: 1372-1377
16. Foresman J B, Frisch Æ. Exploring Chemistry with Electronic Structure Methods, 2nd ed. Pittsburgh, PA: Gaussian Inc., 1996
17. Hohenberg P, Kohn W. Inhomogeneous electron gas. Phys Rev, 1964, 136: B864-B871
18. Chattaraj P K, Nath S, Maiti B. Reactivity descriptors. In: Bultinck P, Winter H D, Langenaeker W, Tollenaere J. Eds. Computational Medicinal Chemistry for Drug Discovery. New York: MarcelDekker, 2003. 295-322, Chapter 11
19. Xi Z, Yu Z H, Niu C W, Ban S R, Yang G F. Development of a general quantum-chemical descriptor for steric effects: Density functional theory based QSAR study of herbicidal sulfonylurea analogues. J Comput Chem, 2006, 27: 1571-1576
20. Petersson G A, Bennett A, Tensfeldt T G, Al-Laham M A, Shirley W A, Mantzaris J. A complete basis set model chemistry. I. The total energies of closed-shell atoms and hydrides of the first-row elements. J Chem Phys, 1988, 89: 2193-2218
21. Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Zakrzewski V G, Montgomery J A, Stratmann R E, Burant J C, Dapprich S, Millam J M, Daniels A D, Kudin K N, Strain M C, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson G A, Ayala P Y, Cui Q, Morokuma K, Rega N, Salvador P, Dannenberg J J, Malick D K, Rabuck A D, Raghavachari K, Foresman J B, Cioslowski J, Ortiz J V, Baboul A G, Stefanov B B, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin R L, Fox D J, Keith T, Al-Laham M A, Peng C Y, Nanayakkara A, Challacombe M, Gill P M W, Johnson B, Chen W, Wong M W, Andres J L, Gonzalez C, Head-Gordon M, Replogle E S, Pople J A. Gaussian 98, Revision A.11.4. Gaussian, Inc., Pittsburgh PA, 2002
22. Ghose A K, Pritchet A, Crippen G M. Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships III: Modeling hydrophobic interactions. J Comp Chem, 1988, 9: 80-90
23. SPSS, vs 9.0; SPSS Inc.: Chicago, IL
24. Schaper K J. Free-Wilson-type analysis of non-additive substituent effects on THPB dopamine receptor affinity using artificial neural networks. Quant Struct Act Relat, 1999, 18: 354-360
25. Tetko I V, Tanchuk V Y, Villa A E. Prediction of n-octanol/water partition coefficients from PHYSPROP database using artificial neural networks and E-state indices. J Chem Inf Comput Sci, 2001, 41: 1407-1421
26. Clark M, Cramer R D. The probability of chance correlation using partial least squares (PLS). Quant Struct Act Relat, 1993, 12: 137-145
27. Yao S W, Lopes V H C, Fernández F, García-Mera X, Morales M, Rodríguez-Borges J E, Cordeiroa M N D S. Synthesis and QSAR study of the anticancer activity of some novel indance carbocyclic nucleosides. Bioorg Med Chem, 2003, 11: 4999-5006
28. Dietrich S W, Dreyer N D, Hansch C, Bentley D L. Confidence interval estimators for parameters associated with quantitative structure-activity relationships. J Med Chem, 1980, 23: 1201-1205
29. Cornish-Bowden A, Wong J T. Evaluation of rate constants for enzyme-catalysed reactions by the jackknife technique. Application to liver alcohol dehydrogenase. Biochem J, 1978, 175: 969-976
30. Huuskonen, J. QSAR Modeling with the electrotopological state: TIBO derivatives. J Chem Inf Comput Sci, 2001, 41: 425-429
31. Pople J A, Gordon M S. Molecular orbital theory of the electronic structure of organic compounds. I. Substituent effects and dipole moments. J Am Chem Soc, 1967, 89: 4253-4261
32. Fliszar S. Charge distribution and chemical effects in saturated hydrocarbons. J Am Chem Soc, 1972, 94: 1068-1073
33. 2+ with DFT Method. J Comput Chem, 2002, 23: 436-443