Synthesis and biological activity of derivatives of the marine quinone avarone

被引：23

作者：

Bozic, Tatjana ^{[1
]}

Novakovic, Irena ^{[2
]}

Gasic, Miroslav J. ^{[3
]}

Juranic, Zorica ^{[4
]}

Stanojkovic, Tatjana ^{[4
]}

Tufegdzic, Srdan ^{[2
]}

Kljajic, Zoran ^{[5
]}

Sladic, Dusan ^{[1
]}

机构：

[1] Univ Belgrade, Fac Sci, Belgrade 11000, Serbia

[2] ICTM, Ctr Chem, Belgrade 11000, Serbia

[3] Serbian Acad Arts & Sci, Belgrade 11001, Serbia

[4] Inst Oncol & Radiol Serbia, Belgrade 11000, Serbia

[5] Inst Marine Biol, Kotor 85330, Montenegro

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2010年 / 45卷 / 03期

关键词：

Marine quinone; Avarone; Alkyl(aryl)thio derivatives; Cytotoxic activity; Cyclic voltammetry; SESQUITERPENE HYDROQUINONE AVAROL; SPONGE DYSIDEA-AVARA; TNF-ALPHA GENERATION; KAPPA-B ACTIVATION; IN-VITRO; ASSAY; INVITRO; VIRUS; INHIBITION; REACTIVITY;

D O I：

10.1016/j.ejmech.2009.11.033

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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 IC50 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 IC50 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.

引用

页码：923 / 929

页数：7

共 41 条

[1] Antipsoriatic effects of avarol-3′-thiosalicylate are mediated by inhibition of TNF-α generation and NF-κB activation in mouse skin [J].