Determination of logP for biologically active chalcones and cyclic chalcone analogs by RPTLC

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Abstract

LogP values of 41 biologically active chalcones (Figure 1, 1) and their cyclic analogs, E-2-(X-benzylidene)-1-indanones (Figure 1, 2), -tetralones (Figure 1, 3) and -benzosuberones (Figure 1, 4) have been determined by an optimized and validated RPTLC method. The optimized RPTLC investigations were performed on silanized silica gel 60F254 as stationary phase with methanol-water, 60 + 40 (v/v) as mobile phase. The RPTLC method was validated by analysis of three drugs, diazepam, progesterone, and PGE1 ethyl ester, with known experimental logP values. The calibration equation used for the logPTLC calculations was: logP = 4.315M + 1.436 (n = 11, r = 0.996, s = 0.02, F = 1089). On the basis of the logPTLC values obtained structure-lipophilicity relationships for the investigated chalcones (1) and cyclic chalcone analogs (2-4) were studied. The effects of ring closure, ring size, and the nature and the position of the aromatic substituents on the logPTLC values of the compounds are discussed.

Original languageEnglish
Pages (from-to)42-46
Number of pages5
JournalJournal of Planar Chromatography - Modern TLC
Volume14
Issue number1
Publication statusPublished - 2001

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Chalcones
Chalcone
Indans
Tetralones
Silica Gel
Diazepam
Calibration
Progesterone
Methanol
Water
Pharmaceutical Preparations
prostaglandin E1 ethyl ester
benzosuberone

Keywords

  • Chalcones
  • E-2-benzylidene-1-benzosuberones
  • LogP determination
  • RPTLC
  • Structure-lipophilicity relationship

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

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title = "Determination of logP for biologically active chalcones and cyclic chalcone analogs by RPTLC",
abstract = "LogP values of 41 biologically active chalcones (Figure 1, 1) and their cyclic analogs, E-2-(X-benzylidene)-1-indanones (Figure 1, 2), -tetralones (Figure 1, 3) and -benzosuberones (Figure 1, 4) have been determined by an optimized and validated RPTLC method. The optimized RPTLC investigations were performed on silanized silica gel 60F254 as stationary phase with methanol-water, 60 + 40 (v/v) as mobile phase. The RPTLC method was validated by analysis of three drugs, diazepam, progesterone, and PGE1 ethyl ester, with known experimental logP values. The calibration equation used for the logPTLC calculations was: logP = 4.315M + 1.436 (n = 11, r = 0.996, s = 0.02, F = 1089). On the basis of the logPTLC values obtained structure-lipophilicity relationships for the investigated chalcones (1) and cyclic chalcone analogs (2-4) were studied. The effects of ring closure, ring size, and the nature and the position of the aromatic substituents on the logPTLC values of the compounds are discussed.",
keywords = "Chalcones, E-2-benzylidene-1-benzosuberones, LogP determination, RPTLC, Structure-lipophilicity relationship",
author = "K. Tak{\'a}cs-Nov{\'a}k and P. Perj{\'e}si and J. V{\'a}mos",
year = "2001",
language = "English",
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pages = "42--46",
journal = "Journal of Planar Chromatography - Modern TLC",
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T1 - Determination of logP for biologically active chalcones and cyclic chalcone analogs by RPTLC

AU - Takács-Novák, K.

AU - Perjési, P.

AU - Vámos, J.

PY - 2001

Y1 - 2001

N2 - LogP values of 41 biologically active chalcones (Figure 1, 1) and their cyclic analogs, E-2-(X-benzylidene)-1-indanones (Figure 1, 2), -tetralones (Figure 1, 3) and -benzosuberones (Figure 1, 4) have been determined by an optimized and validated RPTLC method. The optimized RPTLC investigations were performed on silanized silica gel 60F254 as stationary phase with methanol-water, 60 + 40 (v/v) as mobile phase. The RPTLC method was validated by analysis of three drugs, diazepam, progesterone, and PGE1 ethyl ester, with known experimental logP values. The calibration equation used for the logPTLC calculations was: logP = 4.315M + 1.436 (n = 11, r = 0.996, s = 0.02, F = 1089). On the basis of the logPTLC values obtained structure-lipophilicity relationships for the investigated chalcones (1) and cyclic chalcone analogs (2-4) were studied. The effects of ring closure, ring size, and the nature and the position of the aromatic substituents on the logPTLC values of the compounds are discussed.

AB - LogP values of 41 biologically active chalcones (Figure 1, 1) and their cyclic analogs, E-2-(X-benzylidene)-1-indanones (Figure 1, 2), -tetralones (Figure 1, 3) and -benzosuberones (Figure 1, 4) have been determined by an optimized and validated RPTLC method. The optimized RPTLC investigations were performed on silanized silica gel 60F254 as stationary phase with methanol-water, 60 + 40 (v/v) as mobile phase. The RPTLC method was validated by analysis of three drugs, diazepam, progesterone, and PGE1 ethyl ester, with known experimental logP values. The calibration equation used for the logPTLC calculations was: logP = 4.315M + 1.436 (n = 11, r = 0.996, s = 0.02, F = 1089). On the basis of the logPTLC values obtained structure-lipophilicity relationships for the investigated chalcones (1) and cyclic chalcone analogs (2-4) were studied. The effects of ring closure, ring size, and the nature and the position of the aromatic substituents on the logPTLC values of the compounds are discussed.

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