A DFT-based QSARs study of acetazolamide/sulfanilamide derivatives with carbonic anhydrase (CA-II) isozyme inhibitory activity

International Journal of Molecular Sciences

Volumn 8, Issue 2, 2007, Pages 145-155

  Eroǧlu, Erol ^a   Türkmen, Hasan ^a   Güler, Semra ^a   Palaz, Selami ^a   Oltulu, Oral ^a  

^a HARRAN UNIVERSITY   (Turkey)

Author keywords

Carbonic anhydrase (CA II) inhibitors; DFT; QSAR; Sulfonamides

Indexed keywords

2 (2 BENZYLPIPERAZINOETHANOYLAMINO) 1,3,4 THIADIAZOLE 5 SULFONAMIDE; 2 (2 METHYLPIPERIDINOETHANOYLAMINO) 1,3,4 THIADIAZOLE 5 SULFONAMIDE; 2 (2 MORPHOLINOETHANOYLAMINO) 1,3,4 THIADIAZOLE 5 SULFONAMIDE; 2 (3 METHYLPIPERAZINOPROPIONYLAMINO)1,3,4 THIADIAZOLE 5 SULFONAMIDE; 4 (2 MORPHOLINOETHANOYLAMINO)BENZENE SULFONAMIDE; 4 (3 BENZYLPIPERAZIPROPIONYLAMINO)BENZENE SULFONAMIDE; 4 (3 BENZYLPIPERIDINOPROPIONYLAMINO)BENZENE SULFONAMIDE; 4 (3 METHYLPIPERAZINOPROPIONYLAMINO)BENZENE SULFONAMIDE; 4 (3 METHYLPIPERIDINOPROPIONYLAMINO)BENZENE SULFONAMIDE; 4 (4 MORPHOLINOBUTANOYLAMINO)BENZENE SULFONAMIDE; 4 (5 MORPHOLINOPENTANOYLAMINO)BENZENE SULFONAMIDE; ACETAZOLAMIDE; CARBONATE DEHYDRATASE INHIBITOR; DICLOFENAMIDE; DORZOLAMIDE; ETHOXOLAMIDE; METHAZOLAMIDE; SULFANILAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DENSITY FUNCTIONAL THEORY; DRUG ACTIVITY; DRUG BINDING; DRUG INHIBITION; ENTROPY; ENZYME ACTIVITY; GEOMETRY; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 33947314923     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/i8020145     Document Type: Article

References (32)

1. Kaur, P.; Smitha, R.; Aggarwal, D.; Kapil, M. Acetazolamide: future perspective in topical glaucoma therapeutics. International Journal of Pharmaceutics 2002, 248, 1.
2. Maren, T.H. Carbonic anhydrase: general prospectives and advances in glaucoma research. Drug. Dev. Res. 1987, 10, 255.
3. Pfeiffer, N. Dorzolamide: development and clinical application of a topical carbonic anhydrase inhibitor. Survey Ophthalmol. 1997, 42, 137.
4. Backer, B. Decrease in intraocular pressure in man by a carbonic anhydrase inhibitor (Diamox). Am. J. Ophthalmol. 1954, 37, 13.
5. Turkmen, H.; Durgun, M.; Yilmaztekin, S.; Emul, M.; Innocenti, A.; Vullo, A.; Scozzafava, A.; Supuran, C.T. Carbonic anhydrase inhibitors. Novel sulfanilamide/acetazolamide derivatives obtained by the tail approach and their interaction with the cytosolic isozymes I and II, and the tumor-associated isozyme IX. Bioorganic & Medicinal Chemistry Letters 2005, 15, 367.
6. Karelson, M. Molecular Descriptors in QSAR/QSPR, J. Wiley and Sons, New York, 2000.
7. Tadeschini, R.; Consonni, V. Handbook of Molecular Descriptors, Wiley-VCH, Weinheim, 2000.
8. Clare, B.W.; Supuran, C.T. Semi-empirical atomic charges and dipole moments in hypervalent sulfonamide molecules: descriptors in QSAR studies. Journal of Molecular Structure (Theochem) 1998, 428, 109.
9. Clare, B.W.; Supuran, C.T. Carbonic anhydrase inhibitors. Part 61. Quantum chemical QSAR of a group of benzenedisulfonamides. Eur. J. Med. Chem. 1999, 34, 463.
10. Clare, B.W.; Supuran, C.T. Carbonic anhydrase inhibitors - Part 57: Quantum chemical QSAR of a group of 1,3,4-thiadiazole- and 1,3,4-thiadiazoline disulfonamides with carbonic anhydrase inhibitory properties. Eur. J. Med. Chem. 1999, 34, 41.
11. Trohalaki, S.; Giffort, E.; Pachter, R. Improved QSARs for predictive toxicology of halogenated hydrocarbons. Computers and Chemistry 2000, 24, 421.
12. Zhang, L.; Wan, J.; Yang, G. A DFT-based QSARs study of protoporphyrinogen oxidase inhibitors: phenyl triazolinones. Bioorganic & Medicinal Chemistry 2004, 12, 6183.
13. Singh, P.P.; Srivastava, H.K.; Pasha, F.A. DFT-based QSAR study of testosterone and its derivatives. Bioorganic & Medicinal Chemistry 2004, 12, 171.
14. Dewar, M.; Zoebisch E. G.; Healy, E. F.; Stewart, J.J.B. Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 1993, 115, 5348.
15. Stewart, J.J.B. Optimization of parameters for semiempirical methods I. Method. J. Comp. Chem. 1989, 10, 209.
16. Stewart, J.J.B. Optimization of parameters for semiempirical methods II. Applications. J. Comp. Chem. 1989, 10, 221.
17. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa,M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al- Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, GAUSSIAN 03, Revision B.05, Gaussian, Inc., Pittsburgh, PA, 2003.
18. Parr, R..; Yang, W. Density Functional Theory of Atoms and Molecules, Oxford University Pres, New York, 1989.
19. Becke, A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993, 98, 5648.
20. CODESSA (Comprehensive Descriptors for Structural and Statistical Analysis), Semichem, 7204, Mullen, Shawnee, KS 66216 USA, Copyright© Semichem and the University of Florida, 1995-2004.
21. Foresman, J.B.; Frisch, A.E. Exploring Chemistry with Electronic Structure Methods, second ed., Gaussian Inc., Pittsburgh, PA, 1996.
22. Pedregosa, J.C.; Alzuet, G.; Borras, J.; Fustero, S.; Garcia-Granda, S.; Diaz, M.R. Structure of 5-amino-1,3,4-thiadiazole-2-sulfonamide, an inhibitor of the enzyme carbonic anhydrase. Acta Crystallogr. 1993, C49, 630.
23. Nakayama, A.; Hagiwara, K.; Hashimoto, S.; Shimoda, S. QSAR of fungicidal Δ3-1,2,4-thiadiazolines: reactivity-activity correlation of S-H inhibitors. Quant. Struct.-Act. Relat. 1993, 12, 251.
24. Fukui, K. Theory of Orientation and Stereoselection, Springer- Verlag, New York, 1975.
25. Zhou, Z.; Parr, R.G. Activation hardness: new index for describing the orientation of electrophilic aromatic substitution. J. Am. Chem. Soc. 1990, 112, 5720.
26. Fleming, I. Frontier Orbitals and Organic Chemical Reactions, John Wiley & Sons, New York, 1976.
27. Lewis, D.F.V. Molecular orbital calculations on solvents and other small molecules: Correlation between electronic and molecular properties υ, αMOL, π*, and β. J. Comput. Chem. 1987, 8, 1084.
28. Parr, R.G.; Donnelly, R.A.; Levy, M.; Palke, W.E. Electronegativity: the density functional viewpoint. J. Chem. Phys. 1978, 68, 3801.
29. Iczkowski, R.P.; Margrave, J.L. Electronegativity. J. Am. Chem. Soc. 1961, 83, 3547.
30. Abbate, F.; Casini, A.; Scozzafava, A.; Supuran, C.T. Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with a topically acting antiglaucoma sulfonamide. Bioorg. Med. Chem. Lett. 2004, 14, 2357.
31. Clare, B.W.; Supuran, C.T. Carbonic anhydrase inhibitors Part 41,Quantitative Structure Activity correlations involving kinetic rate constants of 20 sulfonamide inhibitors from a noncongeneric series. Eur. J. Med. Chem. 1997, 32, 311.
32. Vidgren, J.; Liljas, A.; Walker, N.P.C. Refined structure of the acetazolamide complex of human carbonic anhydrase II at 1.9 A. Int. J. Biol. Macromol. 1990, 12, 334.