Synthesis and biological activity of derivatives of the marine quinone avarone
| Autor: | Irena Novaković, Srdan Tufegdzic, Tatjana Stanojković, Dušan Sladić, Zoran Kljajić, M. J. Gasic, Zorica Juranić, T Tatjana Bozic |
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| Rok vydání: | 2010 |
| Předmět: |
Cyclic voltammetry
Anti-HIV Agents Marine quinone Stereochemistry Uterine Cervical Neoplasms Thio Antineoplastic Agents Stereoisomerism 01 natural sciences Chemical synthesis Inhibitory Concentration 50 03 medical and health sciences chemistry.chemical_compound Cell Line Tumor Cyclohexenes Dysidea Drug Discovery Animals Humans Avarone 030304 developmental biology Antibacterial agent Pharmacology 0303 health sciences Molecular Structure Cytotoxic activity 010405 organic chemistry Thiophenol Organic Chemistry Quinones Biological activity Alkyl(aryl)thio derivatives General Medicine Anti-Bacterial Agents 0104 chemical sciences Quinone chemistry HIV-1 Female Artemia Antibacterial activity Sesquiterpenes HeLa Cells |
| Zdroj: | European Journal of Medicinal Chemistry |
| ISSN: | 0223-5234 |
| Popis: | Nine alkyl(aryl)thio derivatives of the marine sesquiterpene quinone avarone were synthesized by nucleophilic addition of thiols or thiophenol to avarone. In most cases only one regioisomer was obtained. Their cytotoxic activities, brine shrimp lethality and antibacterial activity were evaluated, as well as those of some previously synthesized avarone derivatives. Anti-HIV activity of two derivatives was tested. Electrochemical properties were determined for all the derivatives in Order to obtain more accurate information on structure-activity relationships. Most derivatives showed cytotoxic activity against tumor cell lines, with IC(50) values less than 10 mu M for some of them, in particular those with electron-donating substituents. The most active Compound was 4'-(methylamino)avarone, with IC(50) value of 2.4 mu M to melanoma Fem-X cells, and no cytotoxicity to normal lymphocytes. (C) 2009 Elsevier Masson SAS. All Fights reserved. |
| Databáze: | OpenAIRE |
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