CoMFA and CoMSIA studies on 1,3-Bis(benzylidene)-3,4-dihydro-1H-naphthalen- 2-one, 2,6-bis(benzylidene)cyclohexanone, and 3,5-bis(benzylidene)-4-piperidone series of cytotoxic compounds

Journal of Chemical Information and Modeling

Volumn 47, Issue 6, 2007, Pages 2110-2123

  Pately, Maulik R ^a   Dimmock, Jonathan R ^b   Talele, Tanaji T ^a  

^a ST JOHN'S UNIVERSITY   (United States)

^b UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXICITY; ELECTROSTATICS; HYDROPHOBICITY; INFORMATION RETRIEVAL; MOLECULAR STRUCTURE; STATISTICAL METHODS;

CYTOTOXIC COMPOUNDS; STRUCTURAL PARAMETERS;

HYDROCARBONS;

1,3 BIS(BENZYLIDENE) 3,4 DIHYDRO 1H NAPHTHALEN 2 ONE; 1,3-BIS(BENZYLIDENE)-3,4-DIHYDRO-1H-NAPHTHALEN-2-ONE; 2,6 BIS(BENZYLIDENE)CYCLOHEXANONE; 2,6-BIS(BENZYLIDENE)CYCLOHEXANONE; 3,5 BIS(BENZYLIDENE) 4 PIPERIDONE; 3,5-BIS(BENZYLIDENE)-4-PIPERIDONE; CYCLOHEXANONE DERIVATIVE; NAPHTHALENE DERIVATIVE; PIPERIDONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER PROGRAM; DRUG EFFECT; HUMAN; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE;

BINDING SITES; CELL LINE, TUMOR; CELL SURVIVAL; CYCLOHEXANONES; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NAPHTHALENES; PIPERIDONES; SOFTWARE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 37249044647     PISSN: 15499596     EISSN: 1549960X     Source Type: Journal    
DOI: 10.1021/ci700210z     Document Type: Article

References (39)

1. Mutus, B.; Wagner, J. D.; Talpas, G J.; Dimmock, J. R.; Phillips, O. A.; Reid, R. S. 1-p-Chlorophenyl-4,4-dimethyl-5-diethylamino-1penten-3-one hydrobromide, a sulfhydryl-specific compound which reacts irreversibly with protein thiols but reversibly with small molecular weight thiols. Anal. Biochem. 1989, 177, 237-243.
2. Baluja, G.; Municio, A. M.; Vega, S. Reactivity of some α,βunsaturated ketones towards sulfhydryl compounds and their antifungal activity. Chem. Ind. 1964, 2053-2054.
3. Dimmock, J. R.; Raghavan, S. K.; Logan, B. M.; Bigam, G. E. Antileukemic evaluation of some Mannich bases derived from 2-arylidene-l,3-diketones. Eur. J. Med. Chem. 1983, 18, 248-254.
4. Pati, H. N.; Das, U.; Sharma, R. K.; Dimmock, J. R. Cytotoxic thiol alkylators. Mini-Rev. Med. Chem. 2007, 7, 131-139.
5. Benvenuto, J. A.; Connor, T. H.; Monteith, D. K.; Laidlaw, J. L.; Adams, S. C.; Mamey, T. S.; Theiss, J. G Degradation and inactivation of antitumor drugs. J. Pharm. Sci. 1993, 82, 988-991.
6. Espinoza-Fonseca, L. M. The benefits of the multi-target approach in drug design and discovery. Bioorg. Med. Chem. 2006, 14, 896-897.
7. Frantz, S. Playing dirty. Nature 2005, 437, 942-943.
8. Galanski, M.; Keppler, B. K. Searching for the magic bullet: anticancer platinum drugs which can be accumulated or activated in the tumor tissue. Anti-Cancer Agents Med. Chem. 2007, 7, 55-73.
9. Dimmock, J. R.; Arora, V. K.; Wonko, S. K.; Hamon, N. W.; Quail, J. W.; Jia, Z.; Warrington, R. C.; Fang, W. D.; Lee, J. S. 3,5-WsBenzylidene-4- piperidones and related compounds with high activity towards P388 leukemia cells. Drug Des. Delivery 1990, 6, 183-194.
10. Das, U.; Kawase, M.; Sakagami, H.; Ideo, A.; Shimada, J.; Moinar, J.; Baráth, Z.; Bata, Z.; Dimmock, J. R. 3-(3,4,5-Trimethoxyphenyll-oxo-2- propene: a novel pharmacophore displaying potent multidrug resistance reversal and selective toxicity. Bioorg. Med. Chem. 2007, 15, 3373-3380.
11. Das, U.; Alcorn, J.; Shrivastav, A.; Sharma, R. K.; De Clercq, E.; Balzarini, J.; Dimmock, J. R. Design, synthesis and cytotoxic properties of novel 1-[4-(2-alkylaminoethoxy)phenylcarbonyl]-3,5-bis(arylidene)4-piperidones and related compounds. Eur. J. Med. Chem. 2007, 42, 71-80.
12. Das, U.; Gul, H. I.; Alcorn, J.; Shrivastav, A.; George, T.; Sharma, R. K.; Nienaber, K. H.; De Clercq, E.; Balzarini, J.; Kawase, M.; Kan, N.; Tanaka, T.; Tani, S.; Werbovetz, K. A.; Yakovich, A. J.; Manavathu, E. K.; Stables, J. P.; Dimmock, J. R. Cytotoxic 5-aryll-(4-nitrophenyl)-3-oxo-1,4-pentadienes mounted on alicyclic scaffolds. Eur. J. Med. Chem. 2006, 41, 577-585.
13. Das, U.; Selvakumar, P.; Sharma, R. K.; Haas, T. A.; Dimmock, J. R. /V-Acyl-S.S-bis(arylidene)-piperidones and related compounds which stimulate fyn kinase. J. Enzyme Inhib. Med. Chem. 2007, 22, 451 -455.
14. Jha, A.; Mukherjee, C.; Prasad, A. K.; Parmar, V. S.; De Clercq, E.; Balzarini, J.; Stables, J. P.; Manavathu, E. K.; Shrivastav, A.; Sharma, R. K.; Nienaber, K. H.; Zello, G. A.; Dimmock, J. R. E,E,E-1-(4Arylamino-4-oxo-2- butenoyl)-3,5-bis(arylidene)-4-piperidones: a topographical study of some novel potent cytotoxins. Bioorg. Med. Chem. 2007, 15, 5854-5865.
15. Dimmock, J. R.; Kumar, P.; Quail, J. W.; Pugazhenthi, U.; Yang, J.; Chen, M.; Reid, R. S.; Allen, T. M.; Kao, G. Y.; Cole, S. P. C.; Batist, G.; Balzarini, J.; De Clercq, E. Synthesis and cytotoxic evaluation of some styryl ketones and related compounds. Eur. J. Med. Chem. 1995, 30, 209-217.
16. Dimmock, J. R.; Sidhu, K. K.; Chen, M.; Reid, R. S.; Allen, T. M.; Kao, G. Y.; Truitt, G. A. Evaluation of some Mannich bases of cycloalkanones and related compounds for cytotoxic activity. Eur. J. Med. Chem. 1993, 28, 313-322.
17. Mitchell, J. B.; Russo, A. The role of glutathione in radiation and drug induced cytotoxicity. Br. J. Cancer 1987, 55, 96-104.
18. Tsutsui, K.; Komuro, C.; Nishidai, T.; Shibamoto, Y.; Takahashi, M.; Abe, M. Chemosensitization by buthionine sulfoximine in vivo. Int. J. Radiat. Oncol. Biol. Phys. 1986, 12, 1183-1186.
19. Dimmock, J. R.; Padmanilayam, M. P.; Zello, G. A.; Quail, J. W.; Oloo, E. O.; Prisciak, J. S.; Kraatz, H.-B.; Cherkasov, A.; Lee, J. S.; Allen, T. M.; Santos, C. L.; Manavathu, E. K.; De Clercq, E.; Balzarini, J.; Stables, J. P. Cytotoxic 1,3-diarylidene-2-tetralones and related compounds. Eur. J. Med. Chem. 2002, 37, 813-824.
20. Dimmock, J. R.; Padmanilayam, M. P.; Zello, G. A.; Nienaber, K. H.; Allen, T. M.; Santos, C. L.; De Clercq, E.; Balzarini, J.; Manavathu, E. K.; Stables, J. P. Cytotoxic analogues of 2,6-bis(arylidene)cyclohexanones. Eur. J. Med. Chem. 2003, 38, 169-177.
21. Quinn, F. R.; Milne, G. W. A. Toxicities derived from anti-tumor screening data. Fundam. Appl. Toxicol. 1986, 6, 270-277.
22. Dimmock, J. R.; Kumar, P.; Nazarali, A. J.; Motaganahalli, N. L.; Kowalchuk, T. P.; Beazely, M. A.; Quail, J. W.; Oloo, E. O.; Allen, T. M.; Szydlowski, J.; De Clercq, E.; Balzarini, J. Cytotoxic 2,6-bis(arylidene) cyclohexanones and related compounds. Eur. J. Med. Chem. 2000, 35, 967-977.
23. Dimmock, J. R.; Padmanilayam, M. P.; Puthucode, R. N.; Nazarali, A. J.; Motaganahalli, N. L.; Zello, G. A.; Quail, J. W.; Oloo, E. O.; Kraatz, H.-B.; Prisciak, J. S.; Allen, T. M.; Santos, C. L.; Balzarini, J.; De Clercq, E.; Manavathu, E. K. A Conformational and StructureActivity Relationship Study of Cytotoxic 3,5-Bis(arylidene)-4-piperidones and Related N-Acryloyl Analogues. J. Med. Chem. 2001, 44, 586-593.
24. Cramer, R. D.; III; Patterson, D. E.; Bunce, J. D. Comparative Molecular Field Analysis (CoMFA). 1. Effect of Shape on Binding of Steroids to Carrier Proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
25. Cramer, R. D., III; Bunce, J. D.; Patterson, D. E. Crossvalidation, Bootstrapping, and Partial Least Squares Compared with Multiple Regression in Conventional QSAR Studies. Quant. Struct.-Act. Relat. 1988, 7, 18-25.
26. Klebe, G.; Abraham, U.; Mietzner, T. Molecular Similarity Indices in a Comparative Analysis (CoMSIA) of Drug Molecules to Correlate and Predict their Biological Activity. J. Med. Chem. 1994, 37, 4130-4146.
27. SYBYL 7.2; Tripos Inc.: 1699 South Hanley Rd., St. Louis, MO 63144.
28. Clark, M.; Cramer, R. D., III; Van Opdenbosch, N. Validation of the General-Purpose Tripos 5.2 Force Field. J. Comput. Chem. 1989, 10, 982-1012.
29. Gasteiger, J.; Marsili, M. Iterative partial equalization of orbital electronegativity: A rapid access to atomic charges. Tetrahedron 1980, 36, 3219-3228.
30. Patel, M. R.; Talele, T. T. 3D-QSAR studies on Malonyl Coenzyme A Decarboxylase Inhibitors. Bioorg. Med. Chem. 2007, 15, 4470-4481.
31. Viswanadhan, V. N.; Ghose, A. K.; Revenkar, G. R.; Robins, R. K. Atomic physicochemical parameters for three-dimensional structure directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics. J. Chem. Inf. Comput. Sci. 1989, 29, 163-172.
32. Klebe, G. The use of composite crystal field environments in molecular recognition and the de novo design of protein ligands. J. Mol. Biol. 1994, 237, 212-235.
33. Klebe, G.; Mietzner, T.; Weber, F. Methodological developments and strategies for a fast superposition of drug-size molecules. J. Comput.Aided Mol. Des. 1999, 13, 35-49.
34. Wold, S.; Albano, C.; Dunn, W. J.; Edlund, U.; Esbenson, K.; Geladi, P.; Hellberg, S.; Lindburg, W.; Sjostrom, M. In Chemometrics: Mathematics and Statistics in Chemistry; Kowalski, B., Ed.; Reidel: Dordrecht, The Netherlands, 1984; pp 17-95.
35. Staahle, L.; Wold, S. Partial least squares analysis with cross-validation for the two-class problem: A Monte Carlo study. J. Chemom. 1987, 1, 185-196.
36. Wold, S. Cross validatory estimation of the number of components in factor and principal components models. Technometrics 1978,4,397-405.
37. Vong, R.; Geladi, P.; Wold, S.; Esbensen, K. Source contributions to ambient aerosol calculated by discriminant partial least squares regression (PLS). J. Chemom. 1988, 2, 281-296.
38. Bringmann, G.; Rummey, C. 3D QSAR Investigations on antimalarial naphthylisoquinoline alkaloids by comparative molecular similarity indices analysis (CoMSIA), based on different alignment approaches. J. Chem. Inf. Comput. Sci. 2003, 43, 304-316.
39. Bohm, M.; Strzebecher, J.; Klebe, G. Three-Dimensional Quantitative Structure-Activity Relationship Analyses using Comparative Molecular Field Analysis and Comparative Molecular Similarity Analysis to Elucidate Selectivity Differences of Inhibitors Binding to Trypsin, Thrombin, and Factor Xa. J. Med. Chem. 1999, 42, 458-477.