The lipophilicity estimation of 5-arylidene derivates of (2-thio)hydantoin with antimycobacterial activity

Biomedical Chromatography

Volumn 21, Issue 3, 2007, Pages 291-298

  Łazewska, Dorota ^a   Maludziński, Piotr ^a   Szymańska, Ewa ^a   Kieć Kononiwicz, Katarzyna ^a  

^a JAGIELLONIAN UNIVERSITY MEDICAL COLLEGE   (Poland)

Author keywords

(2 thio)hydantoin; Antimycobacterial actvity; Lipophilicity; Log P calculation; Reversed phase TLC

Indexed keywords

HYDRAZINE; THIN LAYER CHROMATOGRAPHY;

(2-THIO)HYDANTOIN; ANTI-MYCOBACTERIAL; ANTIMYCOBACTERIAL ACTIVITY; ANTIMYCOBACTERIAL ACTVITY; HYDANTOINS; LIPOPHILICITY; LOG P CALCULATION; MOBILE PHASIS; REVERSED PHASE TLC; REVERSED-PHASE THIN-LAYER CHROMATOGRAPHY;

ACETONE;

2 THIOHYDANTOIN DERIVATIVE; ACETONE; ISONIAZID; THIOACETAZONE; THIOHYDANTOIN DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ANTIBACTERIAL ACTIVITY; ARTICLE; CALCULATION; COMPUTER MODEL; COMPUTER PROGRAM; CONTROLLED STUDY; DRUG DETERMINATION; DRUG STRUCTURE; GROWTH INHIBITION; LIPOPHILICITY; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PREDICTION; REVERSED PHASE LIQUID CHROMATOGRAPHY; THIN LAYER CHROMATOGRAPHY;

EID: 33947574378     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.755     Document Type: Article

References (21)

1. Biagi GL, Barbaro AM, Gamba MF and Guerra MC. Partition data of penicillins determined by means of reversed-phase thin-layer chromatography. Journal of Chromatography 1969; 41: 371.
2. Biagi GL, Recanatini M, Barbaro AM and Borea PA. Lipohilicity estimation of drugs. Process Control and Quality 1997; 10: 129.
3. Boyce CBC and Milborrow BV. A simple assessment of partition data for correlating structure and biological activity using thin-layer chromatography. Nature 1965; 208: 537.
4. Caron G, Reymond F, Carrupt PA, Girault HH and Testa B. Combined molecular lipophilicity descriptors and their role in understanding intramolecular effects. Pharmaceutical Science and Technology Today 1999; 2: 327.
5. MW by reversed-phase thin-layer chromatography. Journal of Chromatography A 1994; 673: 113.
6. Fujita T, Iwasa J and Hansch C. A new substituent constant, π derived from partition coefficients. Journal of the American Chemical Society 1964; 86: 5175.
7. Hallgas B, Patonay T, Kiss-Szikszai A, Dobos Z, Hollósy F, Erös D, Örfi L, Kéri G and Idei M. Comparison of measured and calculated lipophilicity of substituted aurones and related compounds. Journal of Chromatography B 2004; 801: 229.
8. Hansch C, Leo A and Hoekman D. Exploring QSAR. Hydrophobic, Electronic and Steric Constants. ACS Professional Reference Book: Washington, DC, 1995.
9. Kieć-Kononowicz K and Szymańska E. Antimycobacterial activity of 5-arylidene derivatives of hydantoin. Il Farmaco, 2002; 57: 909.
10. Klimešová V, Palat P, Waisser K and Klimeš J. Combination of molecular modeling and quantitative structure-activity relationship analysis in the study of antimycobacterial activity of pyridine derivatives. International Journal of Pharmacy 2000, 207: 1.
11. Mannhold R and van de Waterbeemd H. Substructure and whole molecular approaches for calculating log P. Journal of Computer-Aided Molecular Design 2001; 15: 337.
12. Mannhold R, Dross K and Sonntag C. Estimation of lipophilicity by reversed-phase thin-layer chromatography. In: Pliška V, Testa B and van de Waterbeemd H (eds). Lipophilicity in Drug Action and Toxicology. VCV: Weinheim 1996; 141.
13. Nasal A, Siluk D and Kaliszan R. Chromatographic parameters in medicinal chemistry and molecular pharmacology. Current Medicine and Chemistry 2003; 10: 381.
14. Pliška V. The role of lipophilicity in biological response to drug and endogenous ligands. In Lipophilicity in Drug Action and Toxicology. VCV: Weinheim 1996; 263.
15. Schoenmakers PJ, Billiet HAH and DeGalan L. Systematic study of ternary solvent behaviour in reversed-phase liquid chromatography. Journal of Chromatography 1981; 218: 261.
16. Sensi P and Grassi GG. Antimycobacterial agents. In: Wolf ME Burger's Medicinal Chemistry and Drug Discovery, 5th edn. Wiley: New York, 1996; 575.
17. Tetko IV. The WWW as a tool to obtain molecular parameters. Mini Reviews in Medicinal Chemisiry 2003; 3: 8-9.
18. Tetko IV and Tanchuk VY. Application of associative neutral networks for prediction of lipophilicity in ALOGPS 2-1 program. Journal Chemical Information and Computer Sciences 2002; 42: 1136.
19. Valkò K. Application of high-performance liquid chromatography based measurements of lipophilicity to model biological distribution. Journal of Chromatography A 2004; 1037: 299.
20. van de Waterbeemd H, Kamsy M, Wagner B and Fischer H. Lipophilicity measurement by reversed phase high performance liquid chromatography (RP-TLC). In: Pliška V, Testa B and van de Waterbeemd H (eds). Lipophilicity in Drug Action and Toxicology. VCV: Weinheim 1996; 73.
21. Wilson HR, Revankar GR and Tolman RL. In vitro and in vivo activity of certain thiosemicarbazones against Trypanosoma cruzi. Journal of Medicinal Chemistry 1974; 17: 760.