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Synthesis of 2,6-diphenylpyrazine derivatives and their DNA binding and cytotoxic properties.
- Source :
-
European journal of medicinal chemistry [Eur J Med Chem] 2005 Dec; Vol. 40 (12), pp. 1206-13. Date of Electronic Publication: 2005 Sep 08. - Publication Year :
- 2005
-
Abstract
- A series of 2,6-diphenylpyrazine derivatives was synthesized from 2,6-dichloropyrazine and 4-methoxyphenylboronic acid using palladium(0) as catalyst in a Suzuki methodology. After deprotection of the hydroxyl, alkylation reactions with different halides afforded compounds 5-8 bearing hydrophilic chains. DNA binding and cytotoxic properties were investigated. Compound 11 bearing imidazoline terminal groups was found to be a potent AT-specific DNA minor groove binder but there was no relationship between DNA interaction and cytotoxicity. However, in all cases the incorporation of the pyrazine ring was found to promote the cytotoxicity of the molecules compared to the corresponding pyridine analogues, previously synthesized.
- Subjects :
- Animals
Binding Sites
Catalysis
Cattle
Cell Line, Tumor
DNA drug effects
DNA Footprinting
Deoxyribonuclease I chemistry
Drug Design
Drug Screening Assays, Antitumor
Humans
Molecular Structure
Palladium chemistry
Pyrazines chemistry
Structure-Activity Relationship
Thymus Gland chemistry
Cell Proliferation drug effects
DNA chemistry
Pyrazines chemical synthesis
Pyrazines pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 0223-5234
- Volume :
- 40
- Issue :
- 12
- Database :
- MEDLINE
- Journal :
- European journal of medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 16153749
- Full Text :
- https://doi.org/10.1016/j.ejmech.2005.07.003