ESTIMATION OF LIPOPHILICITY OF N-SUBSTITUTED 2-ALKYLIDENE-4-OXOTHIAZOLIDINES BY MEANS OF REVERSED-PHASE THIN-LAYER CHROMATOGRAPHY

REFERENCES

• Komsta , L. ; Skibiĭnski , R. ; Berecka , A. ; Gumieniczek , A. ; Radkiewicz , B. ; Radon , M. Revisiting Thin-Layer Chromatography as a Lipophilicity Determination Tool – A Comparative Study on Several Techniques with a Model Solute Set . J. Pharm. Biomed. Anal. 2010 , doi: DOI:10.1016/j.jpba.2010.06.024
   PubMedGoogle Scholar
• Wang , Q. S. ; Zhang , L. Review of Research on Quantitative Structure-Retention Relationship in Thin-Layer Chromatography . J. Liq. Chromatogr. Relat. Technol. 1999 , 22 , 1 – 14 .
   Web of Science ®Google Scholar
• Slawik , T. ; Paw , B. Lipophilicity of Some N- and O-substituted Alkanoic Acids of 1,2-benzisothiazol-3(2H)-one Determined by Reversed-Phase Thin Layer Chromatography . J. Liq. Chromatogr. Relat. Technol. 2004 , 27 , 1043 – 1055 .
   Web of Science ®Google Scholar
• Bate-Smith , E. C. ; Westall , R. G. Chromatographic Behaviour and Chemical Structure I. Some Naturally Occuring Phenolic Substances . Biochim. Biophys. Acta 1950 , 4 , 427 – 440 .
   Web of Science ®Google Scholar
• Soczewinski , E. ; Wachtmeister , C. A. The Relation Between the Composition of Certain Ternary Two-Phase Solvent Systems and R M Values . J. Chromatogr. A 1962 , 7 , 311 – 320 .
   Web of Science ®Google Scholar
• Biagi , G. L. ; Barbaro , A. M. ; Sapone , A. Determination of Lipophilicity by Means of Reversed-Phase Thin-Layer Chromatography: I. Basic Aspects and Relationship Between Slope and Intercept of TLC Equations . J. Chromatogr. A 1994 , 662 , 341 – 361 .
   Web of Science ®Google Scholar
• Cserháti , T. Determination of the Lipophilicity of Some Aniline Derivatives by Reversed-Phase Thin-Layer Chromatography. The Effect of the Organic Phase in the Eluent . Chromatographia 1984 , 18 , 318 – 322 .
   Web of Science ®Google Scholar
• Dross , K. ; Sonntag , C. ; Mannhold , R. Determination of the Hydrophobicity Parameter R M w by Reversed-Phase Thin-Layer Chromatography . J. Chromatogr. A 1994 , 673 , 113 – 124 .
   Web of Science ®Google Scholar
• Bieganowska , M. L. ; Doraczynska , A. ; Petruczynik , A. The Retention Behavior of Some Sulfonamides on Different TLC Plates. 2. Comparison of the Selectivity of the Systems and Quantitative Determination of Hydrophobicity Parameters . J. Planar Chromatogr. 1995 , 8 , 122 – 128 .
   Web of Science ®Google Scholar
• Natić , M. ; Marković , R. ; Anđelković , K. ; Milojković-Opsenica , D. ; Tešić , Ž. Reversed-Phase Thin-Layer Chromatography of Stereodefined 2-Alkylidene-4-Oxothiazolidines and 1,2-Dithioles . J. Planar Chromatogr. 2004 , 17 , 323 – 327 .
   Google Scholar
• Natić , M. ; Marković , R. ; Milojković-Opsenica , D. ; Tešić , Ž. Structure-Retention Relationship Study of Diastereomeric (Z)- and (E)-2-alkylidene-4-oxothiazolidines . J. Sep. Sci. 2007 , 30 , 2241 – 2248 .
   PubMedGoogle Scholar
• Marković , R. ; Baranac , M. ; Juranić , N. ; Macura , S. ; Cekić , I. ; Minić , D. 1H NMR Dynamic Study of Thermal Z/E Isomerization of 5-substituted 2-alkylidene-4-oxothiazolidine Derivatives: Barriers to Rotation About C=C Bond . J. Mol. Struct. 2006 , 800 , 85 – 92 .
   Google Scholar
• Marković , R. ; Shirazi , A. ; Džambaski , Z. ; Baranac , M. ; Minić , D. Configurational Isomerization of Push-Pull Thiazolidinone Derivatives Controlled by Intermolecular and Intramolecular RAHB: 1H NMR Dynamic Investigation of Concentration and Temperature Effects . J. Phys. Org. Chem. 2004 , 17 , 118 – 123 .
   Web of Science ®Google Scholar
• Džambaski , Z. ; Marković , R. ; Stojanović , M. ; Pergal , M. Paper in Preparation.
   Google Scholar
• Satzinger , G. Heterocycles by Reaction of Mercapto and Hydroxycarboxylic Esters with Activated Nitriles . Liebigs Ann. Chem. 1978 , 3 , 473 – 511 .
   Google Scholar
• Markovic , R. ; Baranac , M. ; Steel , P. ; Kleinpeter , E. ; Stojanovic , M. Stereocontrolled Synthesis of New Tetrahydrofuro[2,3-d]thiazole derivatives via Activated Vinylogous Iminium Ions . Heterocycles 2005 , 65 , 2635 – 2647 .
   Google Scholar
• Kralj , D. ; Grošelj , U. ; Meden , A. ; Dahmann , G. ; Stanovnik , B. ; Svete , J. A Simple Synthesis of 4-(2-aminoethyl)-5-hydroxy-1H-pyrazoles . Tetrahedron 2007 , 63 , 11213 – 11222 .
   Google Scholar
• Miller , J. N. ; Miller , J. C. Statistics and Chemometrics for Analytical Chemistry, , 5th Ed. , Pearson : Edinburgh Gate , England , 2005 .
   Google Scholar
• Sarbu , C. ; Casoni , D. ; Darabantu , M. ; Maiereanu , C. Quantitative Structure-Retention and Retention-Activity Relationships of some 1,3-oxazolidine Systems by RP-HPTLC and PCA . J. Pharm. Biomed. Anal. 2004 , 35 , 213 – 219 .
   PubMed Web of Science ®Google Scholar
• Sarbu , C. ; Todor , S. Evaluation of Lipophilicity by Principal Components Analysis . J. Planar Chromatogr. 1998 , 11 , 123 – 126 .
   Web of Science ®Google Scholar
• Sarbu , C. ; Todor , S. Determination of Lipophilicity of Some Non-Steroidal Anti-Inflammatory Agents and Their Relationships by Using Principal Component Analysis Based on Thin-Layer Chromatographic Retention Data . J. Chromatogr. A 1998 , 822 , 263 – 269 .
   PubMed Web of Science ®Google Scholar
• Detroyer , A. ; Vander Heyden , Y. ; Cambre , I. ; Massart , D. L. Chemometric Comparison of Recent Chromatographic and Electrophoretic Methods in a Quantitative Structure-Retention and Retention-Activity Relationship Context . J. Chromatogr. A 2003 , 986 , 227 – 238 .
   PubMed Web of Science ®Google Scholar
• Singh , S. P. ; Parmar , S. S. ; Raman , K. ; Stenberg , V. I. Chemistry and Biological Activity of Thiazolidinones . Chem. Rev. 1981 , 81 , 175 – 203 .
   Web of Science ®Google Scholar
• Faulkner , D. J. Marine Natural Products . Nat. Prod. Rep. 1998 , 15 , 113 – 158 .
   PubMed Web of Science ®Google Scholar
• Sokolenko , N. ; Abbenante , G. ; Scanlon , M. J. ; Jones , A. ; Gahan , L. R. ; Hanson , G. R. ; Fairlie , D. P. Cyclooligomerization of Thiazole-Containing Tetrapeptides. Symmetrical Macrocycles with up to 76 Amino Acids . J. Am. Chem. Soc. 1999 , 121 , 2603 – 2604 .
   Google Scholar
• Küçükgüzel , Ş. G. ; Oruç , E. E. ; Rollas , S. ; Şahin , F. ; Özbek , A. Synthesis, Characterization and Biological Activity of Novel 4-thiazolidino 1,3,4-oxadiazoles and Some Related Compounds . Eur. J. Med. Chem. 2002 , 37 , 197 – 206 .
   PubMed Web of Science ®Google Scholar
• Gududuru , V. ; Hurh , E. ; Dalton , J. T. ; Miller , D. D. Discovery of 2-arylthiazolidine-4-carboxylic Acid Amides as a New Class of Cytotoxic Agents for Prostate Cancer . J. Med. Chem. 2005 , 48 , 2584 – 2588 .
   PubMed Web of Science ®Google Scholar
• Ottanà , R. ; Carotti , S. ; Maccari , R. ; Landini , I. ; Chiricosta , G. ; Caciagli , B. ; Vigorita , M. G. ; Mini , E. In vitro Antiproliferative Activity Against Human Colon Cancer Cell Lines of Representative 4-thiazolidinones. Part I . Bioorg. Med. Chem. Lett. 2005 , 15 , 3930 – 3933 .
   PubMed Web of Science ®Google Scholar
• Hintze , J. NCSS and PASS. Number Cruncher Statistical Systems , Kaysville , Utah , 2001 , www.ncss.com
   Google Scholar
• http://www.vcclab.org/ (accessed March 2011) .
   Google Scholar
• Tetko , I. V. ; Tanchuk , V. Y. Application of Associative Neural Networks for Prediction of Lipophilicity in Alog PS 2.1 Program . J. Chem. Inf. Comp. Sci. 2002 , 42 , 1136 – 1145 .
   PubMedGoogle Scholar
• Tetko , I. V. ; Tanchuk , V. Y. ; Villa , A. E. Prediction of n-octanol/water Partition Coefficients from PHYSPROP Database Using Artificial Neural Networks and E-state Indices . J. Chem. Inf. Comp. Sci. 2001 , 41 , 1407 – 1421 .
   PubMedGoogle Scholar
• http://www.cambridgesoft.com (accessed March 2011) .
   Google Scholar
• Dorsey , J. G. ; Cooper , W. T. Retention Mechanisms of Bonded-Phase Liquid Chromatography . Anal. Chem. 1994 , 66 , 857A – 867A .
   PubMed Web of Science ®Google Scholar
• Foster , M. D. ; Synovec , R. E. Reversed Phase Liquid Chromatography of Organic Hydrocarbons with Water as the Mobile Phase . Anal. Chem. 1996 , 68 , 2838 – 2844 .
   PubMed Web of Science ®Google Scholar
• Meyer , V. Practical High-Performance Liquid Chromatography, , 4th Ed. , John Wiley & Sons : Germany , 2004 .
   Google Scholar