(E)-2-benzylidenebenzocyclanones

Part X. Determination of log P of (E)-3-benzylidene-2,3-dihydro-1-benzopyran-4-ones by RP-TLC. Effect on log P of incorporation of oxygen atom into carbocyclic chalcone analogues

Zsuzsanna Rozmer, P. Perjési

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

log P values of 14 biologically active (E)-3-(X-benzylidene)-2,3-dihydro-1- benzopyran-4-ones (3) have been determined by an optimized and validated reversed-phase thin-layer chromatography (RPTLC) method. The RP-TLC investigations were performed on silanized silica gel 60F254 as stationary phase with methanol-water 60:40 (v/v) as mobile phase. The RP-TLC method was validated by analysis of four drugs, diazepam, progesterone, PGE 1 ethyl ester, and itraconazole, with known log PSF (shake-flask) values. The experimentally determined log PTLC values were compared with the predicted log P values obtained by the CLOGP program. The log PTLC values of the investigated (E)-3-(X-benzylidene)-2,3-dihydro-1-benzopyran- 4-ones (3) were compared with those of the previously investigated structurally related chalcones (1) and (E)-2-(X-benzylidene)-1-tetralones (2). It was found that the log PTLC values of the respective 4′-X-benzylidene analogues increased in the 1 <3 <2 order. The average difference between the log PTLC data of the respective cyclic 4′-X-benzylidene derivatives 2 and 3 was found to be 0.23 log P unit. The effect of the position (ortho, meta, or para) of the aromatic substituents did not follow regularity in either of the two series. The results indicate the importance of both steric and electronic factors in the lipophilicity of the investigated compounds.

Original languageEnglish
Pages (from-to)284-288
Number of pages5
JournalJournal of Planar Chromatography - Modern TLC
Volume26
Issue number3
DOIs
Publication statusPublished - Jun 1 2013

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Chalcone
Tetralones
Chalcones
Oxygen
Thin layer chromatography
Atoms
Itraconazole
Silica Gel
Reverse-Phase Chromatography
Diazepam
Thin Layer Chromatography
Prostaglandins E
Progesterone
Methanol
Esters
Derivatives
Water
Pharmaceutical Preparations
benzopyran-4-one

Keywords

  • (E)-2-benzylidene-1-tetralones
  • (E)-3-benzylidene-2,3-dihydro-1-benzopyran-4-ones
  • Chalcones
  • log P determination
  • RP-TLC
  • Structure- lipophilicity relationship

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry

Cite this

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title = "(E)-2-benzylidenebenzocyclanones: Part X. Determination of log P of (E)-3-benzylidene-2,3-dihydro-1-benzopyran-4-ones by RP-TLC. Effect on log P of incorporation of oxygen atom into carbocyclic chalcone analogues",
abstract = "log P values of 14 biologically active (E)-3-(X-benzylidene)-2,3-dihydro-1- benzopyran-4-ones (3) have been determined by an optimized and validated reversed-phase thin-layer chromatography (RPTLC) method. The RP-TLC investigations were performed on silanized silica gel 60F254 as stationary phase with methanol-water 60:40 (v/v) as mobile phase. The RP-TLC method was validated by analysis of four drugs, diazepam, progesterone, PGE 1 ethyl ester, and itraconazole, with known log PSF (shake-flask) values. The experimentally determined log PTLC values were compared with the predicted log P values obtained by the CLOGP program. The log PTLC values of the investigated (E)-3-(X-benzylidene)-2,3-dihydro-1-benzopyran- 4-ones (3) were compared with those of the previously investigated structurally related chalcones (1) and (E)-2-(X-benzylidene)-1-tetralones (2). It was found that the log PTLC values of the respective 4′-X-benzylidene analogues increased in the 1 <3 <2 order. The average difference between the log PTLC data of the respective cyclic 4′-X-benzylidene derivatives 2 and 3 was found to be 0.23 log P unit. The effect of the position (ortho, meta, or para) of the aromatic substituents did not follow regularity in either of the two series. The results indicate the importance of both steric and electronic factors in the lipophilicity of the investigated compounds.",
keywords = "(E)-2-benzylidene-1-tetralones, (E)-3-benzylidene-2,3-dihydro-1-benzopyran-4-ones, Chalcones, log P determination, RP-TLC, Structure- lipophilicity relationship",
author = "Zsuzsanna Rozmer and P. Perj{\'e}si",
year = "2013",
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day = "1",
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language = "English",
volume = "26",
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TY - JOUR

T1 - (E)-2-benzylidenebenzocyclanones

T2 - Part X. Determination of log P of (E)-3-benzylidene-2,3-dihydro-1-benzopyran-4-ones by RP-TLC. Effect on log P of incorporation of oxygen atom into carbocyclic chalcone analogues

AU - Rozmer, Zsuzsanna

AU - Perjési, P.

PY - 2013/6/1

Y1 - 2013/6/1

N2 - log P values of 14 biologically active (E)-3-(X-benzylidene)-2,3-dihydro-1- benzopyran-4-ones (3) have been determined by an optimized and validated reversed-phase thin-layer chromatography (RPTLC) method. The RP-TLC investigations were performed on silanized silica gel 60F254 as stationary phase with methanol-water 60:40 (v/v) as mobile phase. The RP-TLC method was validated by analysis of four drugs, diazepam, progesterone, PGE 1 ethyl ester, and itraconazole, with known log PSF (shake-flask) values. The experimentally determined log PTLC values were compared with the predicted log P values obtained by the CLOGP program. The log PTLC values of the investigated (E)-3-(X-benzylidene)-2,3-dihydro-1-benzopyran- 4-ones (3) were compared with those of the previously investigated structurally related chalcones (1) and (E)-2-(X-benzylidene)-1-tetralones (2). It was found that the log PTLC values of the respective 4′-X-benzylidene analogues increased in the 1 <3 <2 order. The average difference between the log PTLC data of the respective cyclic 4′-X-benzylidene derivatives 2 and 3 was found to be 0.23 log P unit. The effect of the position (ortho, meta, or para) of the aromatic substituents did not follow regularity in either of the two series. The results indicate the importance of both steric and electronic factors in the lipophilicity of the investigated compounds.

AB - log P values of 14 biologically active (E)-3-(X-benzylidene)-2,3-dihydro-1- benzopyran-4-ones (3) have been determined by an optimized and validated reversed-phase thin-layer chromatography (RPTLC) method. The RP-TLC investigations were performed on silanized silica gel 60F254 as stationary phase with methanol-water 60:40 (v/v) as mobile phase. The RP-TLC method was validated by analysis of four drugs, diazepam, progesterone, PGE 1 ethyl ester, and itraconazole, with known log PSF (shake-flask) values. The experimentally determined log PTLC values were compared with the predicted log P values obtained by the CLOGP program. The log PTLC values of the investigated (E)-3-(X-benzylidene)-2,3-dihydro-1-benzopyran- 4-ones (3) were compared with those of the previously investigated structurally related chalcones (1) and (E)-2-(X-benzylidene)-1-tetralones (2). It was found that the log PTLC values of the respective 4′-X-benzylidene analogues increased in the 1 <3 <2 order. The average difference between the log PTLC data of the respective cyclic 4′-X-benzylidene derivatives 2 and 3 was found to be 0.23 log P unit. The effect of the position (ortho, meta, or para) of the aromatic substituents did not follow regularity in either of the two series. The results indicate the importance of both steric and electronic factors in the lipophilicity of the investigated compounds.

KW - (E)-2-benzylidene-1-tetralones

KW - (E)-3-benzylidene-2,3-dihydro-1-benzopyran-4-ones

KW - Chalcones

KW - log P determination

KW - RP-TLC

KW - Structure- lipophilicity relationship

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U2 - 10.1556/JPC.26.2013.3.14

DO - 10.1556/JPC.26.2013.3.14

M3 - Article

VL - 26

SP - 284

EP - 288

JO - Journal of Planar Chromatography - Modern TLC

JF - Journal of Planar Chromatography - Modern TLC

SN - 0933-4173

IS - 3

ER -