Relationship between the molecular structure and the anticancer activity of N-(2-chloroethyl)-N′-cyclohexyl-N-nitrosoureas: A theoretical investigation

International Journal of Quantum Chemistry

Volumn 112, Issue 3, 2012, Pages 747-758

  Cao, Jun ^a   Zhao, Lijiao ^a   Jin, Shubin ^a   Zhong, Rugang ^a  

^a BEIJING UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

anticancer activity; chloroethyl cyclohexyl nitrosoureas derivatives; DFT; QSAR

Indexed keywords

ALKYLATING AGENTS; ANTI-CANCER AGENTS; ANTICANCER ACTIVITIES; BASIS SETS; CLINICAL TREATMENTS; DESCRIPTORS; DFT; EXPERIMENTAL DATA; GEOMETRY OPTIMIZATION; LIPOPHILICITY; MULTIPLE LINEAR REGRESSIONS; N-OCTANOL; NITROSOUREAS; PARTITION COEFFICIENT; POSITIVE CORRELATIONS; QSAR; QSAR ANALYSIS; QSAR MODEL; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS; RETRO-ENE REACTION; STEPWISE MULTIPLE REGRESSION; STRUCTURE ACTIVITY RELATIONSHIPS; THEORETICAL INVESTIGATIONS;

ACTIVATION ENERGY; ALCOHOLS; DENSITY FUNCTIONAL THEORY; MOLECULAR GRAPHICS; UREA;

COMPUTATIONAL CHEMISTRY;

EID: 84255214224     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.23042     Document Type: Article

References (59)

1. Gnewuch, C. T.,;, Sosnovsky, G., Chem Rev 1997, 97, 829.
2. Lawley, P. D.,;, Phillips, D. H., Mutat Res -Fund Mol M 1996, 355, 13.
3. Lemoine, A.,;, Lucas, C.,;, Ings, R. M. J., Xenobiotica 1991, 21, 775.
4. Bodell, W. J., J Neuro-Oncol 2009, 91, 257.
5. Ueda-Kawamitsu, H.,;, Lawson, T. A.,;, Gwilt, P. R., Biochem Pharmacol 2002, 63, 1209.
6. Yamaguchi, T.,;, Kanemitsu, H.,;, Yamamoto, S.,;, Komatsu, M.,;, Uemura, H.,;, Tamura, K.,;, Shirai, T., J Toxicol Pathol 2010, 23, 25.
7. Bodell, W. J.,;, Pongracz, K., Chem Res Toxicol 1993, 6, 434.
8. Fischhaber, P. L.,;, Gall, A. S.,;, Duncan, J. A.,;, Hopkins, P. B., Cancer Res 1999, 59, 4363.
9. Chen, F. X.,;, Bodell, W. J.,;, Liang, G. N.,;, Gold, B., Chem Res Toxicol 1996, 9, 208.
10. Penketh, P. G.,;, Shyam, K.,;, Sartorelli, A. C., Anal Biochem 1997, 252, 210.
11. Erickson, L. C.,;, Laurent, G.,;, Sharkey, N. A.,;, Kohn, K. W., Nature 1980, 288, 727.
12. Minnick, D. T.,;, Gerson, S. L.,;, Dumenco, L. L.,;, Veigl, M. L.,;, Sedwick, W. D., Cancer Res 1993, 53, 997.
13. Bodell, W. J., Mutat Res 1990, 233, 203.
14. Wiencke, J. K.,;, Wiemels, J., Mutat Res -Rev Gen Toxicol 1995, 339, 91.
15. Bodell, W. J., Mutat Res -Fund Mol M 2003, 522, 85.
16. Dolan, M. E., Adv Drug Deliv Rev 1997, 26, 105.
17. Some Pharmaceutical Drug: IARC Monographs on the Evaluation of Carcinogenic Risks to Humans; IARC Press: Lyon, 1996.
18. Stewart, B. W.,;, Kleihues, P., World Cancer Report; IARC Press: Lyon, 2003.
19. Hansch, C.,;, Leo, A.,;, Schmidt, C.,;, Jow, P. Y. C.,;, Montgomery, J. A., J Med Chem 1980, 23, 1095.
20. Panasci, L. C.,;, Green, D.,;, Nagourney, R.,;, Fox, P.,;, Schein, P. S., Cancer Res 1977, 37, 2615.
21. Hansch, C.,;, Smith, N.,;, Engle, R.,;, Wood, H., Cancer Chemother Rep 1972, 56, 443.
22. Montgomery, J. A.,;, Mayo, J. G.,;, Hansch, C., J Med Chem 1974, 17, 477.
23. Helguera, A. M.,;, Cordeiro, M.,;, Perez, M. A. C.,;, Combes, R. D.,;, Gonzalez, M. P., Tox Appl Pharmacol 2008, 231, 197.
24. Helguera, A. M.,;, Gonzalez, M. P.,;, Cordeiro, M.,;, Perez, M. A. C., Tox Appl Pharmacol 2007, 221, 189.
25. Helguera, A. M.,;, Gonzalez, M. P.,;, Cordeiro, M.,;, Perez, M. A. C., Chem Res Toxicol 2008, 21, 633.
26. Helguera, A. M.,;, Perez, M. A. C.,;, Gonzalez, M. P.,;, Ruiz, R. M.,;, Diaz, H. G., Bioorg Med Chem 2005, 13, 2477.
27. Luan, F.,;, Zhang, R. S.,;, Zhao, C. Y.,;, Yao, X. J.,;, Liu, M. C.,;, Hu, Z. D.,;, Fan, B. T., Chem Res Toxicol 2005, 18, 198.
28. Sarmah, P.,;, Deka, R. C., J Comput Aided Mol Des 2009, 23, 343.
29. Azizi, K.,;, Safarpour, M. A.,;, Keykhaee, M.,;, Mehdipour, A. R., J Mol Model 2009, 15, 1509.
30. Fernandez, M.,;, Caballero, J., J Mol Model 2007, 13, 465.
31. Becke, A. D., Phy Rev A 1988, 38, 3098.
32. Becke, A. D., J Chem Phy 1993, 98, 5648.
33. Sarkar, A.,;, Mostafa, G., J Mol Model 2009, 15, 1221.
34. Zhu, M. J.,;, Ge, F.,;, Zhu, R. L.,;, Wang, X. Y.,;, Zheng, X. Y., Chemosphere 2010, 80, 46.
35. Chen, J. C.,;, Shen, Y.,;, Liao, S. Y.,;, Chen, L. M.,;, Zheng, K. C., Int J Quantum Chem 2007, 107, 1468.
36. Dai, Y. J.,;, Zhang, X.,;, Zhang, X. L.,;, Wang, H. J.,;, Lu, Z. S., J Mol Model 2008, 14, 807.
37. Deeb, O.,;, Clare, B. W., Chem Bio Drug Des 2008, 71, 352.
38. Dolezal, R.,;, van Damme, S.,;, Bultinck, P.,;, Waisser, K., Eur J Med Chem 2009, 44, 869.
39. Ebenso, E. E.,;, Arslan, T.,;, Kandemirli, F.,;, Caner, N.,;, Love, I., Int J Quantum Chem 2010, 110, 1003.
40. Nikolic, K.,;, Agababa, D., J Mol Graph Model 2009, 27, 777.
41. Nikolic, K.,;, Filipic, S.,;, Agbaba, D., Sar Qsar Environ Res 2009, 20, 133.
42. Oltulu, O.,;, Yasar, M. M.,;, Eroglu, E., Eur J Med Chem 2009, 44, 3439.
43. Sarmah, P.,;, Deka, R. C., Int J Quantum Chem 2008, 108, 1400.
44. Tawari, N. R.,;, Degani, M. S., J Comput Chem 2010, 31, 739.
45. Cossi, M.,;, Rega, N.,;, Scalmani, G.,;, Barone, V., J Comput Chem 2003, 24, 669.
46. Cossi, M.,;, Scalmani, G.,;, Rega, N.,;, Barone, V., J Chem Phy 2002, 117, 43.
47. Frisch, M. J. T., G. W.,;, Schlegel, H. B.,;, Scuseria, G. E.,;, Robb, M. A.,;, Cheeseman, J. R.,;, Montgomery, J. A.,;, Vreven, T., Jr.,;, Kudin, K. N.,;, Burant, J. C.,;, Millam, J. M.,;, Iyengar, S. S.,;, Tomasi, J.,;, Barone, V.,;, Mennucci, B.,;, Cossi, M.,;, Scalmani, G.,;, Rega, N.,;, Petersson, G. A.,;, Nakatsuji, H.,;, Hada, M.,;, Ehara, M.,;, Toyota, K.,;, Fukuda, R.,;, Hasegawa, J.,;, Ishida, M.,;, Nakajima, T.,;, Honda, Y.,;, Kitao, O.,;, Nakai, H.,;, Klene, M.,;, Li, X.,;, Knox, J. E.,;, Hratchian, H. P.,;, Cross, J. B.,;, Adamo, C.,;, Jaramillo, J.,;, Gomperts, R.,;, Stratmann, R. E.,;, Yazyev, O.,;, Austin, A. J.,;, Cammi, R.,;, Pomelli, C.,;, Ochterski, J. W.,;, Ayala, P. Y.,;, Morokuma, K.,;, Voth, G. A.,;, Salvador, P.,;, Dannenberg, J. J.,;, Zakrzewski, V. G.,;, Dapprich, S.,;, Daniels, A. D.,;, Strain, M. C.,;, Farkas, O.,;, Malick, D. K.,;, Rabuck, A. D.,;, Raghavachari, K.,;, Foresman, J. B.,;, Ortiz, J. V.,;, Cui, Q.,;, Baboul, A. G.,;, Clifford, S.,;, Cioslowski, J.,;, Stefanov, B. B.,;, Liu, G.,;, Liashenko, A.,;, Piskorz, P.,;, Komaromi, I.,;, 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.,;, Gonzalez, C.,; and, Pople, J. A., Gaussian, Inc.: Wallingford, CT, 2004.
48. http://www.molinspiration.com/cgi-bin/properties, 2011.
49. Nie, N. H.,;, Hull, C. H.,;, Bent, D. H., Statistical Product and Service Solutions; SPSS, Inc.: Chicago, Illinois, 2004.
50. Michejda, C. J.,;, Koepke, S. R., J Am Chem Soc 1978, 100, 1959.
51. Brundrett, R. B., J Med Chem 1980, 23, 1245.
52. Jabbari, A.,;, Sorensen, E. J.,;, Houk, K. N., Org Lett 2006, 8, 3105.
53. Wu, H.,;, Loeppky, R. N.,;, Glaser, R., J Org Chem 2005, 70, 6790.
54. Amado, S.,;, GarciaRio, L.,;, Leis, J. R.,;, Rios, A., J Chem Soc -Perkin Trans 1996, 2235.
55. Golding, B. T.,;, Bleasdale, C.,;, McGinnis, J.,;, Muller, S.,;, Rees, H. T.,;, Rees, N. H.,;, Farmer, P. B.,;, Watson, W. P., Tetrahedron 1997, 53, 4063.
56. Snyder, J. K.,;, Stock, L. M., J Org Chem 1980, 45, 1990.
57. Loeppky, R. N.,;, Yu, L.,;, Gu, F.,;, Ye, Q. P., J Am Chem Soc 1996, 118, 10995.
58. Zhao, L. J.,;, Zhong, R. G.,;, She, Y. B.,;, Dai, Q. H., Acta Phy Chim Sin 2005, 21, 883.
59. Zhao, L. J.,;, Zhong, R. G.,;, Yuan, X. L.,;, Cui, Y. S.,;, Dai, Q. H., Chinese Sci Bull 2004, 49, 1450.