The Effect of Phenyl Substituents on C-13 NMR Shifts and Metal Ions Binding to 4-Phenyl-2,4-Dioxobutanoic Acid Derivatives

Tatjana Z. Verbic; Branko J. Drakulic; Mire Zloh; Ivan O. Juranic

The Effect of Phenyl Substituents on C-13 NMR Shifts and Metal Ions Binding to 4-Phenyl-2,4-Dioxobutanoic Acid Derivatives

Tatjana Z. Verbic, Branko J. Drakulic, Mire Zloh, Ivan O. Juranic

School of Life and Medical Sciences

Research output: Contribution to journal › Article › peer-review

Abstract

Butanoic moiety of 4-aryl-2,4-dioxobutanoic acids is involved in interactions with metal ions within HIV-1 integrase active site. Sixteen congeneric 4-phenyl-2,4-dioxobutanoic acid derivatives with different substitution on the phenyl ring were prepared. Effects of substitution were studied by spectrometric methods (NMR, MS, UV/VIS) and linear free energy relationships. Better metal complexation ability of meta-alkyl substituted compounds, was observed. This observation might have pharmacological implications.

Original language	English
Pages (from-to)	692-699
Number of pages	8
Journal	Letters in Organic Chemistry
Volume	5
Issue number	8
Publication status	Published - Dec 2008

Keywords

DESIGN
metal complexation ability
UV/VIS spectroscopy
PHARMACOPHORE
DISCOVERY
MS
KETO-ENOL TAUTOMERIZATION
UPDATE
4-Aryl-2,4-dioxobutanoic acids
BETA-DIKETONES
MODEL
Linear free energy relationships
NMR
HIV-1 INTEGRASE INHIBITORS
CHARACTER

Cite this

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title = "The Effect of Phenyl Substituents on C-13 NMR Shifts and Metal Ions Binding to 4-Phenyl-2,4-Dioxobutanoic Acid Derivatives",

abstract = "Butanoic moiety of 4-aryl-2,4-dioxobutanoic acids is involved in interactions with metal ions within HIV-1 integrase active site. Sixteen congeneric 4-phenyl-2,4-dioxobutanoic acid derivatives with different substitution on the phenyl ring were prepared. Effects of substitution were studied by spectrometric methods (NMR, MS, UV/VIS) and linear free energy relationships. Better metal complexation ability of meta-alkyl substituted compounds, was observed. This observation might have pharmacological implications.",

keywords = "DESIGN, metal complexation ability, UV/VIS spectroscopy, PHARMACOPHORE, DISCOVERY, MS, KETO-ENOL TAUTOMERIZATION, UPDATE, 4-Aryl-2,4-dioxobutanoic acids, BETA-DIKETONES, MODEL, Linear free energy relationships, NMR, HIV-1 INTEGRASE INHIBITORS, CHARACTER",

author = "Verbic, {Tatjana Z.} and Drakulic, {Branko J.} and Mire Zloh and Juranic, {Ivan O.}",

year = "2008",

month = dec,

language = "English",

volume = "5",

pages = "692--699",

journal = "Letters in Organic Chemistry",

issn = "1570-1786",

publisher = "Bentham Science Publishers B.V.",

number = "8",

}

TY - JOUR

T1 - The Effect of Phenyl Substituents on C-13 NMR Shifts and Metal Ions Binding to 4-Phenyl-2,4-Dioxobutanoic Acid Derivatives

AU - Verbic, Tatjana Z.

AU - Drakulic, Branko J.

AU - Zloh, Mire

AU - Juranic, Ivan O.

PY - 2008/12

Y1 - 2008/12

N2 - Butanoic moiety of 4-aryl-2,4-dioxobutanoic acids is involved in interactions with metal ions within HIV-1 integrase active site. Sixteen congeneric 4-phenyl-2,4-dioxobutanoic acid derivatives with different substitution on the phenyl ring were prepared. Effects of substitution were studied by spectrometric methods (NMR, MS, UV/VIS) and linear free energy relationships. Better metal complexation ability of meta-alkyl substituted compounds, was observed. This observation might have pharmacological implications.

AB - Butanoic moiety of 4-aryl-2,4-dioxobutanoic acids is involved in interactions with metal ions within HIV-1 integrase active site. Sixteen congeneric 4-phenyl-2,4-dioxobutanoic acid derivatives with different substitution on the phenyl ring were prepared. Effects of substitution were studied by spectrometric methods (NMR, MS, UV/VIS) and linear free energy relationships. Better metal complexation ability of meta-alkyl substituted compounds, was observed. This observation might have pharmacological implications.

KW - DESIGN

KW - metal complexation ability

KW - UV/VIS spectroscopy

KW - PHARMACOPHORE

KW - DISCOVERY

KW - MS

KW - KETO-ENOL TAUTOMERIZATION

KW - UPDATE

KW - 4-Aryl-2,4-dioxobutanoic acids

KW - BETA-DIKETONES

KW - MODEL

KW - Linear free energy relationships

KW - NMR

KW - HIV-1 INTEGRASE INHIBITORS

KW - CHARACTER

M3 - Article

SN - 1570-1786

VL - 5

SP - 692

EP - 699

JO - Letters in Organic Chemistry

JF - Letters in Organic Chemistry

IS - 8

ER -

The Effect of Phenyl Substituents on C-13 NMR Shifts and Metal Ions Binding to 4-Phenyl-2,4-Dioxobutanoic Acid Derivatives

Abstract

Keywords

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