Use of Quantitative Structure - Activity Relationship (QSAR) and ADMET prediction studies as screening methods for design of benzyl urea derivatives for anti-cancer activity

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 26, Issue 3, 2011, Pages 319-331

  Lokwani, Deepak ^a   Bhandari, Shashikant ^a   Pujari, Radha ^b   Shastri, Padma ^b   Shelke, Ganesh ^b   Pawar, Vidya ^a  

^a AISSMS COLLEGE OF PHARMACY   (India)

^b NATIONAL CENTRE FOR CELL SCIENCE   (India)

Author keywords

ADMET; Anti cancer; k nearest neighbour molecular field analysis (kNN MFA); QSAR

Indexed keywords

1 (2 CHLOROBENZYL) 3,3 DIMETHYL 1 (NAPHTHALEN 1 YL)UREA; 1 (2 ETHYLBENZYL) 3,3 DIMETHYL 1 (NAPHTHALEN 1 YL)UREA; 1 (2,3 DIMETHYLPHENYL) 1 (2 ETHYLBENZYL) 3,3 DIMETHYLUREA; 1 (2,3 DIMETHYLPHENYL) 3,3 DIMETHYL 1 (2 NITROBENZYL)UREA; 1 (3 ETHOXY 4 HYDROXYBENZYL) 3,3 DIMETHYL 1 (NAPHTHALEN 1 YL)UREA; 1 BENZYL 1 (2 CHLOROBENZYL) 3,3 DIMETHYLUREA; 1 BENZYL 3,3 DIMETHYL 1 (2 NITROBENZYL)UREA; BENZYL DERIVATIVE; FLUOROURACIL; GEFITINIB; IMATINIB; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG ABSORPTION; DRUG DESIGN; DRUG DISTRIBUTION; DRUG EXCRETION; DRUG METABOLISM; DRUG SAFETY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL LINE; LIVER TOXICITY; MITOSIS INHIBITION; MYELOID LEUKEMIA; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; T CELL LEUKEMIA;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; PREDICTIVE VALUE OF TESTS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; STRUCTURE-ACTIVITY RELATIONSHIP; UREA;

EID: 79955564493     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2010.506437     Document Type: Article

References (33)

1. Chabner BA, Roberts TG Jr. Timeline: Chemotherapy and the war on cancer. Nat Rev Cancer 2005; 5:65-72.
2. Workman P. Genomics and the second golden era of cancer drug development. Mol Biosyst 2005; 1:17-26. (Pubitemid 43349726)
3. Druker BJ. Perspectives on the development of a molecularly targeted agent. Cancer Cell 2002; 1:31-36. (Pubitemid 41039173)
4. Morin MJ. From oncogene to drug: development of small molecule tyrosine kinase inhibitors as anti-tumor and anti-angiogenic agents. Oncogene 2000; 19:6574-6583. (Pubitemid 32197695)
5. Krause DS, Van Etten RA. Tyrosine kinases as targets for cancer therapy. N Engl J Med 2005; 353:172-187. (Pubitemid 41058349)
6. Hirsch FR, Varella-Garcia M, Bunn PA Jr, Di Maria MV, Veve R, Bremmes RM, Barón AE, Zeng C, Franklin WA. Epidermal growth factor receptor in non-small-cell lung carcinomas: correlation between gene copy number and protein expression and impact on prognosis. J Clin Oncol 2003; 21:3798-3807. (Pubitemid 46606235)
7. Grünwald V, Hidalgo M. Developing inhibitors of the epidermal growth factor receptor for cancer treatment. J Natl Cancer Inst 2003; 95:851-867. (Pubitemid 36833877)
8. Bridges AJ. Chemical inhibitors of protein kinases. Chem Rev 2001; 101:2541-2572.
9. Kobayashi S, Boggon TJ, Dayaram T, Jänne PA, Kocher O, Meyerson M, Johnson BE, Eck MJ, Tenen DG, Halmos B. EGFR mutation and resistance of non-small-cell lung cancer to gefitinib. N Engl J Med 2005; 352:786-792. (Pubitemid 40271173)
10. Yamamotoa H, Toyookaa S, Mitsudomib T. Impact of EGFR mutation analysis in non-small cell lung cancer. Lung Cancer 2009; 63:315-321.
11. Kwak EL, Sordella R, Bell DW, Godin-Heymann N, Okimoto RA, Brannigan BW, Harris PL, Driscoll DR, Fidias P, Lynch TJ, Rabindran SK, McGinnis JP, Wissner A, Sharma SV, Isselbacher KJ, Settleman J, Haber DA. Irreversible inhibitors of the EGF receptor may circumvent acquired resistance to gefitinib. Proc Natl Acad Sci USA 2005; 102:7665-7670. (Pubitemid 40741028)
12. Shimshoni JA, Bialer M, Wlodarczyk B, Finnell RH, Yagen B. Potent anticonvulsant urea derivatives of constitutional isomers of valproic acid. J Med Chem 2007; 50:6419-6427. (Pubitemid 350250429)
13. Fortin JS, Lacroix J, Desjardins M, Patenaude A, Petitclerc E, C-Gaudreault R. Alkylation potency and protein specificity of aromatic urea derivatives and bioisosteres as potential irreversible antagonists of the colchicine-binding site. Bioorg Med Chem 2007; 15:4456-4469. (Pubitemid 46777295)
14. Watson RJ, Allen DR, Birch HL, Chapman GA, Galvin FC, Jopling LA, Knight RL, Meier D, Oliver K, Meissner JW, Owen DA, Thomas EJ, Tremayne N, Williams SC. Development of CXCR3 antagonists. Part 3: Tropenyl and homotropenyl-piperidine urea derivatives. Bioorg Med Chem Lett 2008; 18:147-151.
15. Li HQ, Zhu TT, Yan T, Luo Y, Zhu HL. Design, synthesis and structureactivity relationships of antiproliferative 1,3-disubstituted urea derivatives. Eur J Med Chem 2009; 44:453-459.
16. Cao P, Huang XF, Ding H, Ge HM, Li HQ, Ruan BF, Zhu HL. Synthesis and cytotoxic evaluation of substituted urea derivatives as inhibitors of human-leukemia K562 cells. Chem Biodivers 2007; 4:881-886. (Pubitemid 46930004)
17. Dzimbeg G, Zorc B, Kralj M, Ester K, Pavelic K, Andrei G, Snoeck R, Balzarini J, De Clercq E, Mintas M. The novel primaquine derivatives of N-alkyl, cycloalkyl or aryl urea: synthesis, cytostatic and antiviral activity evaluations. Eur J Med Chem 2008; 43:1180-1187.
18. Bechard P, Lacroix J, Poyet P, C-Gaudreault R. Synthesis and cytotoxic activity of new alkyl[3-(2-chloroethyl)ureido]benzene derivative. Eur J Med Chem 1994; 29:963-966.
19. Ling S, Xin Z, Zhong J, Jian-xin F. Synthesis, Structure, and Biological Activity of Novel 4,5-Disubstituted Thiazolyl Urea Derivatives. Hetero Chem 2008; 19:2-6.
20. Gonzalez-Díaz H, Saiz-Urra L, Molina R, Santana L, Uriarte E. A model for the recognition of protein kinases based on the entropy of 3D van der Waals interactions. J Proteome Res 2007; 6:904-908. (Pubitemid 46340196)
21. González-Díaz H, Saíz-Urra L, Molina R, González-Díaz Y, Sánchez-González A. Computational chemistry approach to protein kinase recognition using 3D stochastic van der Waals spectral moments. J Comput Chem 2007; 28:1042-1048. (Pubitemid 46506707)
22. Szántai-Kis C, Kövesdi I, Eros D, Bánhegyi P, Ullrich A, Kéri G, Orfi L. Prediction oriented QSAR modelling of EGFR inhibition. Curr Med Chem 2006; 13:277-287.
23. Shi WM, Shen Q, Kong W, Ye BX. QSAR analysis of tyrosine kinase inhibitor using modified ant colony optimization and multiple linear regression. Eur J Med Chem 2007; 42:81-86. (Pubitemid 46198984)
24. Peng T, Pei J, Zhou J. 3D-QSAR and receptor modeling of tyrosine kinase inhibitors with flexible atom receptor model (FLARM). J Chem Inf Comput Sci 2003; 43:298-303.
25. Kamath S, Buolamwini JK. Receptor-guided alignment-based comparative 3D-QSAR studies of benzylidene malonitrile tyrphostins as EGFR and HER-2 kinase inhibitors. J Med Chem 2003; 46:4657-4668. (Pubitemid 37271615)
26. Assefa H, Kamath S, Buolamwini JK. 3D-QSAR and docking studies on 4-anilinoquinazoline and 4-anilinoquinoline epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors. J Comput Aided Mol Des 2003; 17:475-493. (Pubitemid 38008961)
27. Hansch C, Leo A. Exploring QSAR. In: Heller SR. Fundamentals and Applications in Chemistry and Biology, American Chemical Society, Wasshington, 1995
28. Zheng W, Tropsha A. Novel variable selection quantitative structure-property relationship approach based on the k-nearestneighbor principle. J Chem Inf Comput Sci 2000; 40:185-194.
29. Ajmani S, Jadhav K, Kulkarni SA. Three-dimensional QSAR using the k-nearest neighbor method and its interpretation. J Chem Inf Model 2006; 46:24-31. (Pubitemid 43282095)
30. VLifeMDS; Molecular Design Suite version 3.5, V-life Sciences Technologies Pvt. Ltd., Pune, India, 2004. (www.vlifesciences. com).
31. Hudson BD, Rahr RM, Wood J, Osman J. Parameter Based Methods for Compound Selection from Chemical Databases. Quant Struct- Act Relat 1996; 15:285-289. (Pubitemid 26283514)
32. Baumann K. An alignment-independent versatile structure descriptor for QSAR and QSPR based on the distribution of molecular features. J Chem Inf Comput Sci 2002; 42:26-35. (Pubitemid 35359022)
33. Discovery Studio, version 2.1; Accelrys Inc.: San Diego, CA, USA.