Synthesis and carbonic anhydrase inhibitory properties of novel cyclohexanonyl bromophenol derivatives

被引：42

作者：

Balaydin, Halis T. ^{[1
,2
]}

Senturk, Murat ^{[3
]}

Menzek, Abdullah ^{[2
]}

机构：

[1] Artvin Coruh Univ, Fac Educ, TR-08000 Artvin, Turkey

[2] Ataturk Univ, Dept Chem, TR-25240 Erzurum, Turkey

[3] Ibrahim Cecen Univ Agri, Dept Chem, TR-04100 Agri, Turkey

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 03期

关键词：

Carbonic anhydrase; Enzyme inhibition; Bromination; Bromophenols; Cyclohexanone with benzyl; Enamine; Esterification; Symphyoketone; IN-VITRO INHIBITION; ERYTHROCYTE GLUTATHIONE-REDUCTASE; ALGA SYMPHYOCLADIA-LATIUSCULA; AROMATIC/HETEROCYCLIC SULFONAMIDES; THERAPEUTIC APPLICATIONS; ODONTHALIA-CORYMBIFERA; PHENOLIC-COMPOUNDS; HUMAN SERUM; ISOZYME-II; PURIFICATION;

D O I：

10.1016/j.bmcl.2011.12.069

中图分类号：

R914 [药物化学];

学科分类号：

100705 [微生物与生化药学];

摘要：

The Naturally occurring novel cyclohexanonyl bromophenol 2(R)-2-(2,3,6-tribromo-4,5-dihydroxybenzyl) cyclohexanone (4) was synthesized as a racemic compound. Cyclohexylphenyl methane derivatives (10-17) with Br, OMe, CO, and OH were also obtained. Inhibition of four human carbonic anhydrase (hCA, EC 4.2.1.1) isozymes I, II, IV, and VI, with compounds 2-4, 8, and 10-26 was investigated. These compounds were found to be promising carbonic anhydrase inhibitors and some of them showed interesting inhibitory activity. Some of the compounds investigated here showed effective hCA inhibitory activity, and might be used as leads for generating novel carbonic anhydrase inhibitors which are valuable drug candidates for the treatment of glaucoma, epilepsy, gastric and duodenal ulcers, neurological disorders, and osteoporosis. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：1352 / 1357

页数：6

共 61 条

[1]

Total Synthesis of the Biologically Active, Naturally Occurring 3,4-Dibromo-5-[2-bromo-3,4-dihydroxy-6-(methoxymethyl)benzyl]benzene-1,2-diol and Regioselective O-Demethylation of Aryl Methyl Ethers [J].

Akbaba, Yusuf ;

Balaydin, Halis Tuerker ;

Goksu, Sueleyman ;

Sahin, Ertan ;

Menzek, Abdullah .

HELVETICA CHIMICA ACTA, 2010, 93 (06) :1127-1135

[2]

A novel and one-pot synthesis of new 1-tosyl pyrrol-2-one derivatives and analysis of carbonic anhydrase inhibitory potencies [J].

Alp, Cemalettin ;

Ekinci, Deniz ;

Gultekin, Mehmet Serdar ;

Senturk, Murat ;

Sahin, Ertan ;

Kufrevioglu, Omer Irfan .

BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (12) :4468-4474

[3]

[Anonymous], [No title captured]

[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]

Inhibition of human carbonic anhydrase isozymes I, II and VI with a series of bisphenol, methoxy and bromophenol compounds [J].

Balaydin, Halis Turker ;

Durdagi, Serdar ;

Ekinci, Deniz ;

Senturk, Murat ;

Goksu, Suleyman ;

Menzek, Abdullah .

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2012, 27 (04) :467-475

[7]

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

[8]

Inhibition of carbonic anhydrase II by thioxolone: A mechanistic and structural study [J].

Barrese, Albert A. ;

Genis, Caroli ;

Fisher, S. Zoe ;

Orwenyo, Jared N. ;

Kumara, Mudalige Thilak ;

Dutta, Subodh K. ;

Phillips, Eric ;

Kiddle, James J. ;

Tu, Chingkuang ;

Silverman, David N. ;

Govindasamy, Lakshmanan ;

Agbandje-McKenna, Mavis ;

McKenna, Robert ;

Tripp, Brian C. .

BIOCHEMISTRY, 2008, 47 (10) :3174-3184

[9]

In vitro inhibition of salicylic acid derivatives on human cytosolic carbonic anhydrase isozymes I and II [J].

Bayram, Esra ;

Senturk, Murat ;

Kufrevioglu, O. Irfan ;

Supuran, Claudiu T. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (20) :9101-9105

[10]

BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3

← 1 2 3 4 5 6 7 →