Relationship between physicochemical properties, lipophilicity parameters, and local anesthetic activity of dibasic esters of phenylcarbamic acid
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I. Malík
,
E. Sedlárová
Abstract
The basic physicochemical properties, lipophilicity parameters of dibasic alkyloxy-substituted phenylcarbamic acids were estimated. For the prepared set of compounds the experimentally obtained solubility, acidity, and lipophilicity parameters were correlated with those computed using various computer programs based on the associative artificial neural network and fragmental methods. The results of pharmacological evaluation were used as entry data for the complex correlations.
[1] Löfgren, N. and Tegner, C., Acta Chem. Scand. 14, 486 (1960). http://dx.doi.org/10.3891/acta.chem.scand.14-048610.3891/acta.chem.scand.14-0486Search in Google Scholar
[2] Pokorná, M., Cesk. Slov. Farm. 47, 14 (1998) (in Czech). Search in Google Scholar
[3] Sládková, D. and Čižmárik, J., Pharmazie 55, 540 (2000). Search in Google Scholar
[4] Csöllei, J., Búčiová, L., Čižmárik, J., and Kopáčová, L., Cesk. Slov. Farm. 42, 93 (1993) (in Slovak). Search in Google Scholar
[5] Chalabala, M., Martincová, R., and Benková, M., Pharmacopoea Slovaca PhS 1, 1st Edition, p. 22. Herba, Bratislava, 1999 (in Slovak). Search in Google Scholar
[6] Remko, M. and von der Lieth, C.-W., Bioorg. Med. Chem. 12, 5395 (2004). http://dx.doi.org/10.1016/j.bmc.2004.07.04910.1016/j.bmc.2004.07.049Search in Google Scholar PubMed
[7] http://ibmlc2.chem.uga.edu/sparc/ Search in Google Scholar
[8] Hilal, H. S., Karickhoff, W. S., and Carreira, A. L., QSAR Comb. Sci. 23, 709 (2004). http://dx.doi.org/10.1002/qsar.20043086610.1002/qsar.200430866Search in Google Scholar
[9] Malík, I., Sedlárová, E., Čižmárik, J., Andriamainty, F., and Csöllei, J., Farm. Obzor 74, 211 (2005). Search in Google Scholar
[10] Gyürösiová, L., Sedlarová, E., and Čižmárik, J., Chem. Pap. 56, 340 (2002). Search in Google Scholar
[11] Tetko, I. V., Gasteiger, J., Todeschini, R., Mauri, A., Livingstone, D., Ertl, P., Palyulin, V. A., Radchenko, E. V., Zefirov, N. S., Makarenko, A. S., Tanchuk, V. Y., and Prokopenko, V. V., J. Comput.-Aided Mol. Des. 19, 453 (2005). http://dx.doi.org/10.1007/s10822-005-8694-y10.1007/s10822-005-8694-ySearch in Google Scholar PubMed
[12] Tetko, I. V. and Tanchuk, V. Y., J. Chem. Inf. Comput. Sci. 42, 1136 (2002). http://dx.doi.org/10.1021/ci025515j10.1021/ci025515jSearch in Google Scholar PubMed
[13] Meylan, W. M. and Howard, P. H., J. Pharm. Sci. 84, 83 (1995). http://dx.doi.org/10.1002/jps.260084012010.1002/jps.2600840120Search in Google Scholar PubMed
[14] Leo, A. J. and Hoekman, D., Perspect. Drug Discovery Des. 18, 19 (2000). http://dx.doi.org/10.1023/A:100873911075310.1023/A:1008739110753Search in Google Scholar
[15] Wang, R., Fu, Y., and Lai, L., J. Chem. Inf. Comput. Sci. 37, 615 (1997). http://dx.doi.org/10.1021/ci960169p10.1021/ci960169pSearch in Google Scholar
[16] http://www.molinspiration.com Search in Google Scholar
[17] Mannhold, R. and Petrauskas, A., QSAR Comb. Sci. 22, 466 (2003). http://dx.doi.org/10.1002/qsar.20039003610.1002/qsar.200390036Search in Google Scholar
[18] Sekera, A. and Vrba, Č., Naturwissenschaften 43, 303 (1956) (in German). http://dx.doi.org/10.1007/BF0062955510.1007/BF00629555Search in Google Scholar
[19] http://www.chemexper.com/tools/propertyExplorer/main.html Search in Google Scholar
[20] http://ccinfoweb.ccsso.ca/rtecs/guide.pdf Search in Google Scholar
[21] Tantishaiyakul, V., J. Pharm. Biomed. Anal. 37, 411 (2005). http://dx.doi.org/10.1016/j.jpba.2004.11.00510.1016/j.jpba.2004.11.005Search in Google Scholar PubMed
[22] Yan, A. X. and Gasteiger, J., QSAR Comb. Sci. 22, 821 (2003). http://dx.doi.org/10.1002/qsar.20033082210.1002/qsar.200330822Search in Google Scholar
[23] Remko, M., Swart, M., and Bickelhaupt, M. F., Bioorg. Med. Chem. 14, 1715 (2006). http://dx.doi.org/10.1016/j.bmc.2005.10.02010.1016/j.bmc.2005.10.020Search in Google Scholar PubMed
[24] Hille, B., J. Gen. Physiol. 69, 475 (1977). http://dx.doi.org/10.1085/jgp.69.4.47510.1085/jgp.69.4.475Search in Google Scholar PubMed PubMed Central
[25] Lin, H.-Ch., Ueda, I., and Eyring, H., Proc. Natl. Acad. Sci. USA 73, 3726 (1976). http://dx.doi.org/10.1073/pnas.73.10.372610.1073/pnas.73.10.3726Search in Google Scholar PubMed PubMed Central
[26] Liu, H. J., Atkins, J., and Kass, R. S., J. Gen. Physiol. 121, 199 (2003). http://dx.doi.org/10.1085/jgp.2002872310.1085/jgp.20028723Search in Google Scholar PubMed PubMed Central
[27] Lee, P. J., Sunami, A., and Fozzard, H. A., Circ. Res. 89, 1014 (2001). Search in Google Scholar
[28] Wang, G. K., J. Gen. Physiol. 92, 747 (1988). http://dx.doi.org/10.1085/jgp.92.6.74710.1085/jgp.92.6.747Search in Google Scholar PubMed PubMed Central
[29] Sanchez, V., Arthur, G. R., and Strichartz, G. R., Anesth. Analg. (N.Y.) 66, 159 (1987). http://dx.doi.org/10.1213/00000539-198666020-0001110.1213/00000539-198666020-00011Search in Google Scholar
[30] Čižmárik, J., Lehotay, J., Nga, P. T. V., and Bednáriková, A., Pharmazie 48, 149 (1993). Search in Google Scholar
[31] Poole, S. K. and Poole, C. F., J. Chromatogr., B: Biomed. Appl. 797, 3 (2003). http://dx.doi.org/10.1016/j.jchromb.2003.08.03210.1016/j.jchromb.2003.08.032Search in Google Scholar PubMed
[32] Remko, M., Medicínska chémia (Medicinal Chemistry), p. 193. Slovak Academic Press, Bratislava, 2002. Search in Google Scholar
[33] http://redpoll.pharmacy.ualberta.ca/drugbank/index.html Search in Google Scholar
[34] Wishart, D. S., Knox, C., Guo, A. C., Shrivastava, S., Hassanali, M., Stothard, P., Chang, Z., and Woolsey, J., Nucleic Acids Res. 34, D668 (2006). http://dx.doi.org/10.1093/nar/gkj06710.1093/nar/gkj067Search in Google Scholar PubMed PubMed Central
[35] Kubinyi, H., QSAR: Hansch Analysis and Related Approaches. VCH, Weinheim, 1993. 10.1002/9783527616824Search in Google Scholar
[36] Račanská, E. and Gregáň, F., Pharmazie 54, 68 (1999). Search in Google Scholar
[37] Balgavý, P. and Devínsky, F., Adv. Colloid Interface Sci. 66, 23 (1996). http://dx.doi.org/10.1016/0001-8686(96)00295-310.1016/0001-8686(96)00295-3Search in Google Scholar
[38] Balgavý, P., Andriamainty, F., Yaradaikin, S., Gallová, J., and Uhríková, D., Scr. Med. 68, 7 (1995). Search in Google Scholar
© 2007 Institute of Chemistry, Slovak Academy of Sciences
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Articles in the same Issue
- A review of methods for synthesis of nanostructured metals with emphasis on iron compounds
- Effect of selenium oxidation state on cadmium translocation in chamomile plants
- Optimization of ammonium nitrate concentration in single-stage continuous cultures of Aspergillus niger with biomass retention
- Behaviour of inorganic constituents of municipal sewage sludge during fluidized-bed combustion
- Profile distribution of As(III) and As(V) species in soil and groundwater in Bozanta area
- Structure of cyano-bridged Eu(III)—Co(III) bimetallic assembly and its application to photophysical verification of photomagnetic phenomenon
- Synthesis and characterization of oligo-4-[(pyridin-3-ylimino)methyl]phenol
- Relationship between physicochemical properties, lipophilicity parameters, and local anesthetic activity of dibasic esters of phenylcarbamic acid
- Improved DPPH determination for antioxidant activity spectrophotometric assay
- Notes on notation of sodium oxofluoroaluminate anions
- Determination of the enthalpy of fusion of Na3FeF6
- Controlled solvothermal synthesis of PbS quasi-nanorods by calix[4]arene
- Palladium-catalyzed heck and suzuki coupling in glycerol
- Synthesis of new condensed and cyclized coumarin derivatives
- M. Hartman, O. Trnka, and M. Pohořelý: Fluidization behavior of oil-contaminated sand
