Relationship between physicochemical properties, lipophilicity parameters, and local anesthetic activity of dibasic esters of phenylcarbamic acid
-
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.14-0486Suche in Google Scholar
[2] Pokorná, M., Cesk. Slov. Farm. 47, 14 (1998) (in Czech). Suche in Google Scholar
[3] Sládková, D. and Čižmárik, J., Pharmazie 55, 540 (2000). Suche in Google Scholar
[4] Csöllei, J., Búčiová, L., Čižmárik, J., and Kopáčová, L., Cesk. Slov. Farm. 42, 93 (1993) (in Slovak). Suche in Google Scholar
[5] Chalabala, M., Martincová, R., and Benková, M., Pharmacopoea Slovaca PhS 1, 1st Edition, p. 22. Herba, Bratislava, 1999 (in Slovak). Suche 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.2004.07.049Suche in Google Scholar PubMed
[7] http://ibmlc2.chem.uga.edu/sparc/ Suche 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.200430866Suche in Google Scholar
[9] Malík, I., Sedlárová, E., Čižmárik, J., Andriamainty, F., and Csöllei, J., Farm. Obzor 74, 211 (2005). Suche in Google Scholar
[10] Gyürösiová, L., Sedlarová, E., and Čižmárik, J., Chem. Pap. 56, 340 (2002). Suche 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-ySuche 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/ci025515jSuche 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.2600840120Suche 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:1008739110753Suche 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/ci960169pSuche in Google Scholar
[16] http://www.molinspiration.com Suche 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.200390036Suche in Google Scholar
[18] Sekera, A. and Vrba, Č., Naturwissenschaften 43, 303 (1956) (in German). http://dx.doi.org/10.1007/BF0062955510.1007/BF00629555Suche in Google Scholar
[19] http://www.chemexper.com/tools/propertyExplorer/main.html Suche in Google Scholar
[20] http://ccinfoweb.ccsso.ca/rtecs/guide.pdf Suche 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.2004.11.005Suche 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.200330822Suche 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.2005.10.020Suche 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.69.4.475Suche 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.73.10.3726Suche 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.20028723Suche in Google Scholar PubMed PubMed Central
[27] Lee, P. J., Sunami, A., and Fozzard, H. A., Circ. Res. 89, 1014 (2001). Suche 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.92.6.747Suche 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/10.1213/00000539-198666020-0001110.1213/00000539-198666020-00011Suche in Google Scholar
[30] Čižmárik, J., Lehotay, J., Nga, P. T. V., and Bednáriková, A., Pharmazie 48, 149 (1993). Suche 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.2003.08.032Suche in Google Scholar PubMed
[32] Remko, M., Medicínska chémia (Medicinal Chemistry), p. 193. Slovak Academic Press, Bratislava, 2002. Suche in Google Scholar
[33] http://redpoll.pharmacy.ualberta.ca/drugbank/index.html Suche 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/gkj067Suche in Google Scholar PubMed PubMed Central
[35] Kubinyi, H., QSAR: Hansch Analysis and Related Approaches. VCH, Weinheim, 1993. 10.1002/9783527616824Suche in Google Scholar
[36] Račanská, E. and Gregáň, F., Pharmazie 54, 68 (1999). Suche 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)00295-3Suche in Google Scholar
[38] Balgavý, P., Andriamainty, F., Yaradaikin, S., Gallová, J., and Uhríková, D., Scr. Med. 68, 7 (1995). Suche in Google Scholar
© 2007 Institute of Chemistry, Slovak Academy of Sciences
Artikel in diesem Heft
- 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
Artikel in diesem Heft
- 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
