Synthesis and paroxonase activities of novel bromophenols

被引：54

作者：

Akbaba, Yusuf ^{[1
]}

Turkes, Cuneyt ^{[1
]}

Polat, Leyla ^{[1
]}

Soyut, Hakan ^{[1
]}

Sahin, Ertan ^{[1
]}

Menzek, Abdullah ^{[1
]}

Goksu, Suleyman ^{[1
]}

Beydemir, Sukru ^{[1
]}

机构：

[1] Ataturk Univ, Dept Chem, Fac Sci, TR-25240 Erzurum, Turkey

来源：

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY | 2013年 / 28卷 / 05期

关键词：

Bromination; bromophenols; natural products; demethylation; paroxonase activity; IN-VITRO; CARBONIC-ANHYDRASE; PARAOXONASE; ANESTHETICS; PON1;

D O I：

10.3109/14756366.2012.715287

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Three novel bromophenols 10-12 were synthesized. Acylation of veratrole (4) with 2,3-dimethoxy benzoic acid (5) gave a kown diarylmethanone 6. Bromination of 6 with different equivalents of molecular bromine afforded new di and tribrominated compounds 7-9 which were converted to their corresponding bromophenols 10-12 via O-demethylation with BBr3. Paraoxonase-1 (PON1) was purified from human serum with approximately 42% and 3584 U x mg(-1) specific activity. The synthesized compounds 6-12 showed inhibitory effects on paraoxonase-1 (PON1) which is an organophosphate (OP) hydrolyser and an antioxidant bioscavenger enzyme. IC50 values were determined in the range of 0.123-1.212 mM. [GRAPHICS] .

引用

页码：1073 / 1079

页数：7

共 28 条

[1] Intravenous anesthetics inhibit human paraoxonase-1 (PON1) activity in vitro and in vivo [J].

Alici, Haci Ahmed ;

Ekinci, Deniz ;

Beydemir, Suekrue .

CLINICAL BIOCHEMISTRY, 2008, 41 (16-17) :1384-1390

[2] Decreased Serum Paraoxonase 1 Activity and Increased Serum Homocysteine and Malondialdehyde Levels in Age-Related Macular Degeneration [J].

Ates, Orhan ;

Azizi, Sedat ;

Alp, H. Hakan ;

Kiziltunc, Ahmet ;

Beydemir, Sukru ;

Cinici, Emine ;

Kocer, Ibrahim ;

Baykal, Orhan .

TOHOKU JOURNAL OF EXPERIMENTAL MEDICINE, 2009, 217 (01) :17-22

[3] Paraoxonase inhibits high-density lipoprotein oxidation and preserves its functions - A possible peroxidative role for paraoxonase [J].

Aviram, M ;

Rosenblat, M ;

Bisgaier, CL ;

Newton, RS ;

Primo-Parmo, SL ;

La Du, BN .

JOURNAL OF CLINICAL INVESTIGATION, 1998, 101 (08) :1581-1590

[4] First and short syntheses of biologically active, naturally occurring brominated mono- and dibenzyl phenols [J].

Balaydin, Halis T. ;

Akbaba, Yusuf ;

Menzek, Abdullah ;

Sahin, Ertan ;

Goksu, Suleyman .

ARKIVOC, 2009, :75-87

[5] Synthesis and carbonic anhydrase inhibitory properties of novel bromophenols including natural products [J].

Balaydin, Halis Turker ;

Soyut, Hakan ;

Ekinci, Deniz ;

Goksu, Suleyman ;

Beydemir, Sukru ;

Menzek, Abdullah ;

Sahin, Ertan .

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2012, 27 (01) :43-50

[6] Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product [J].

Balaydin, Halis Turker ;

Gulcin, Ilhami ;

Menzek, Abdullah ;

Goksu, Suleyman ;

Sahin, Ertan .

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2010, 25 (05) :685-695

[7] Evaluation of the impacts of antibiotic drugs on PON 1; a major bioscavenger against cardiovascular diseases [J].

Ekinci, Deniz ;

Beydemir, Suekrue .

EUROPEAN JOURNAL OF PHARMACOLOGY, 2009, 617 (1-3) :84-89

[8] Effect of some analgesics on Paraoxonase-1 purified from human serum [J].

Ekinci, Deniz ;

Beydemir, Suekrue .

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2009, 24 (04) :1034-1039

[9] An alternative synthesis of the dopaminergic drug 2-amino-1,2,3,4-tetrahydronaphthalene-5,6-diol (5,6-ADTN) [J].

Göksu, S ;

Seçen, H ;

Sütbeyaz, Y .

HELVETICA CHIMICA ACTA, 2006, 89 (02) :270-273

[10] Concise syntheses of 2-aminoindans via indan-2-ol [J].

Göksu, S ;

Seçen, H .

TETRAHEDRON, 2005, 61 (28) :6801-6807

← 1 2 3 →