Abstract
Sulfonamide is one of the most important chemical groups in drug design because sulfonamide derivatives are stable in living cells and water soluble. In this study, we assessed the validity of quantum chemical methods and basis sets for the geometrical parameters of various sulfonamides compared to crystallographic data. Introducing f-type polarization functions into basis sets improved the geometry optimizations using Hartree-Fock, MP2, and B3LYP, indicating that f-type polarization functions play an important role in the description of chemical bonds in sulfonamide derivatives.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Drew J (2000) Drug discovery: a historical perspective. Science 287:1960–1964
Supuran CT, Innocenti A, Mastrolorenzo A, Scozzafava A (2004) Antiviral sulfonamide derivatives. Mini Rev Med Chem 4:189–200
Maren TH (1976) Relations between structure and biological activity of sulfonamides. Annu Rev Pharmacol Toxicol 16:309–327
Supuran CT, Casini A, Scozzafava A (2003) Protease inhibitors of the sulfonamide type: anticancer, antiinflammatory, and antiviral agents. Med Res Rev 23:535–558
Supuran CT (2002) Indisulam. IDrugs 5:1075–1079
Ornstein PL, Arnold MB, Allen NK, Bleisch T, Borromeo PS, Lugar CW, Leander JD, Lodge D, Schoepp DD (1996) Structure-activity studies of 6-substituted decahydroisoquinoline-3-carboxylic acid AMPA receptor antagonists. 2. Effects of distal acid bioisosteric substitution, absolute stereochemical preferences, and in vivo activity. J Med Chem 39:2232–2244
Johansson A, Poliakov A, Åkerblom E, Wiklund K, Lindeberg G, Winiwarter S, Danielson UH, Samuelsson B, Hallberg A (2003) Acyl sulfonamides as potent protease inhibitors of the hepatitis C virus full-length NS3 (protease-helicase/NTPase): a comparative study of different C-terminals. Bioorg Med Chem 11:2551–2568
Rönn R, Gossas T, Sabnis YA, Daoud H, Åkerblom E, Danielson UH, Sandström A (2007) Evaluation of a diverse set of potential P1 carboxylic acid bioisosteres in hepatitis C virus NS3 protease inhibitors. Bioorg Med Chem 15:4057–4068
Allen FH (2002) The Cambridge structural database: a quarter of a million crystal structures and rising. Acta Crystallogr B 58:380–388
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE (2000) The protein data bank. Nucleic Acids Res 28:235–242
Ohwada T (2001) Nitrogen pyramidal amides and related compounds. Yakugaku Zasshi 121:65–77
Parkin A, Collins A, Gilmore CJ, Wilson CC (2008) Using small molecule crystal structure data to obtain information about sulfonamide conformation. Acta Crystallogr B 64:66–77
Taft CA, da Silva VB, de Paula da Silva CHT (2008) Current topics in computer-aided drug design. J Pharm Sci 97:1089–1098
Cai C, Li Z, Wang W, Chen Y (2004) Advances in modeling of biomolecular interactions. Acta Pharmacol Sin 25:1–8
Kapetanovic IM (2008) Computer-aided drug discovery and development (CADDD): In silico-chemico-biological approach. Chem Biol Interact 171:165–176
Clark M, Cramer RDI, van den Opdenbosch N (1989) Validation of the general purpose Tripos 5.2 force field. J Comput Chem 10:982–1012
Wang J, Wolf RM, Caldwell JW, Kollman PA, Case DA (2004) Development and testing of a general amber force field. J Comput Chem 25:1157–1174
Bindal RD, Golab JT, Katzenellenbogen JA (1990) Ab initio calculations on N-methylmethanesulfonamide and methyl methanesulfonate for the development of force field torsional parameters and their use in the conformational analysis of some novel estrogens. J Am Chem Soc 112:7861–7868
Nicholas JB, Vance R, Martin E, Burke BJ, Hopfinger AJ (1991) A molecular mechanics valence force field for sulfonamides derived by ab initio methods. J Phys Chem 95:9803–9811
Liang G, Bays JP, Bowen JP (1997) Ab initio calculations and molecular mechanics (MM3) force field development for sulfonamide and its alkyl derivatives. J Mol Struct (THEOCHEM) 401:165–179
Vijay D, Priyakumar UD, Sastry GN (2004) Basis set and method dependence of the relative energies of C2S2H2 isomers. Chem Phys Lett 383:192–197
Denis PA (2005) Basis set requirements for sulfur compounds in density functional theory: a comparison between correlation-consistent, polarized-consistent, and Pople-type basis sets. J Chem Theory Comput 1:900–907
Niu S, Nichols JA, Ichiye T (2009) Optimization of spin-unrestricted density functional theory for redox properties of rubredoxin redox site analogues. J Chem Theory Comput 5:1361–1368
Gregory DD, Jenks WS (2003) Computational investigation of vicinal disulfoxides and other sulfinyl radical dimers. J Phys Chem A 107:3414–3423
Elguero J, Goya P, Rozas I (1989) An ab initio comparative study of the electronic properties of sulfonamides and amides. J Mol Struct (THEOCHEM) 184:115–129
Heyd J, Thiel W, Weber W (1997) Rotation and inversion barriers in N-methylmethanesulfonamide from ab initio calculations. J Mol Struct (THEOCHEM) 391: 125–130
Stewart JJP (2001) MOPAC2002 1.0. Fujitsu Ltd, Tokyo
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, 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 JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, Revision D.01. Gaussian, Inc., Wallingford
Case DA, Darden TA, Cheatham TE III, Simmerling CL, Wang J, Duke RE, Luo R, Merz KM, Pearlman DA, Crowley M, Walker RC, Zhang W, Wang B, Hayik S, Roitberg A, Seabra G, Wong KF, Paesani F, Wu X, Brozell S, Tsui V, Gohlke H, Yang L, Tan C, Mongan J, Hornak V, Cui G, Beroza P, Mathews DH, Schafmeister C, Ross WS, Kollman PA (2006) AMBER9. University of California, San Francisco
Jakalian A, Bush BL, Jack DB, Bayly CI (2000) Fast, efficient generation of high-quality atomic charges. AM1-BCC Model: I. Method. J Comput Chem 21:132–146
Wang J, Wang W, Kollman PA, Case DA (2006) Automatic atom type and bond type perception in molecular mechanical calculations. J Mol Graph Model 25:247–260
Higgs TC, Parkin A, Parsons S, Tasker PA (2002) N-Methylmethanesulfonamide at 150 K. Acta Crystallogr E 58:o523–o525
Acknowledgments
The present study was performed under the Cooperative Research Program of the Institute for Protein Research, Osaka University. Parts of the computational results in this research were obtained using supercomputing resources at the Cyberscience Center, Tohoku University; the Research Center for Computational Science, Okazaki; and the Cybermedia Center at Osaka University. Yu Takano is grateful to the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan, for the Grant-in-Aid for Scientific Research on Innovative Areas “Materials Design through Computics” (23104506). Akifumi Oda was supported by a Grant-in-Aid for Scientific Research (23790137) from the Japan Society for the Promotion of Science.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2012 Springer Science+Business Media Dordrecht
About this paper
Cite this paper
Oda, A., Takano, Y., Takahashi, O. (2012). Validation of Quantum Chemical Calculations for Sulfonamide Geometrical Parameters. In: Nishikawa, K., Maruani, J., Brändas, E., Delgado-Barrio, G., Piecuch, P. (eds) Quantum Systems in Chemistry and Physics. Progress in Theoretical Chemistry and Physics, vol 26. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-5297-9_17
Download citation
DOI: https://doi.org/10.1007/978-94-007-5297-9_17
Published:
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-007-5296-2
Online ISBN: 978-94-007-5297-9
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)