9,10-Dibromo-N-aryl-9,10-dihydro-9,10-[3,4]epipyrroloanthracene-12,14-diones: Synthesis and Investigation of Their Effects on Carbonic Anhydrase Isozymes I, II, IX, and XII

被引：34

作者：

Goksu, Haydar ^{[1
,2
]}

Topal, Meryem ^{[3
]}

Keskin, Ali ^{[2
]}

Gultekin, Mehmet S. ^{[2
]}

Celik, Murat ^{[2
]}

Gulcin, Ilhami ^{[2
,4
]}

Tanc, Muhammet ^{[5
]}

Supuran, Claudiu T. ^{[5
]}

机构：

[1] Duzce Univ, Kaynasli Vocat Coll, Duzce, Turkey

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

[3] Gumushane Univ, Vocat Sch Hlth Serv, Dept Med Serv & Tech, Gumushane, Turkey

[4] King Saud Univ, Dept Zool, Coll Sci, Riyadh, Saudi Arabia

[5] Univ Florence, Dipartimento NEUROFARBA, Sez Sci Farmaceut, Florence, Italy

来源：

ARCHIV DER PHARMAZIE | 2016年 / 349卷 / 06期

关键词：

Carbonic anhydrase; Enzyme inhibition; Enzyme purification; Isoenzyme; TROUT ONCORHYNCHUS-MYKISS; ACETYLCHOLINE ESTERASE INHIBITORS; ISOENZYMES HCA I; THERAPEUTIC APPLICATIONS; ENZYME-ACTIVITY; MYCOBACTERIUM-TUBERCULOSIS; SULFONAMIDE DERIVATIVES; SELECTIVE INHIBITORS; TUMOR-GROWTH; VIVO;

D O I：

10.1002/ardp.201600047

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

N-substituted maleimides were synthesized from maleic anhydride and primary amines. 1,4-Dibromodibenzo[e,h]bicyclo-[2,2,2]octane-2,3-dicarboximide derivatives (4a-f) were prepared by the [4+2] cycloaddition reaction of dibromoanthracenes with the N-substituted maleimide derivatives. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory effects of the new derivatives were assayed against the human (h) isozymes hCA I, II, IX, and XII. All tested bicyclo dicarboximide derivatives exhibited excellent inhibitory effects in the nanomolar range, with K-i values in the range of 117.73-232.87 nM against hCA I and of 69.74-111.51 nM against hCA II, whereas they were low micromolar inhibitors against hCA IX and XII.

引用

页码：466 / 474

页数：9

共 95 条

[1] Inhibition of tumor-associated human carbonic anhydrase isozymes IX and XII by a new class of substituted-phenylacetamido aromatic sulfonamides [J].

Akdemir, Atilla ;

Guzel-Akdemir, Ozlen ;

Scozzafava, Andrea ;

Capasso, Clemente ;

Supuran, Claudiu T. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (17) :5228-5232

[2] Discovery of potent carbonic anhydrase and acetylcholine esterase inhibitors: Novel sulfamoylcarbamates and sulfamides derived from acetophenones [J].

Akincioglu, Akin ;

Akincioglu, Hulya ;

Gulcin, Ilhami ;

Durdagi, Serdar ;

Supuran, Claudiu T. ;

Goksu, Suleyman .

BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (13) :3592-3602

[3] Novel Sulphamides and Sulphonamides Incorporating the Tetralin Scaffold as Carbonic Anhydrase and Acetylcholine Esterase Inhibitors [J].

Akincioglu, Akin ;

Topal, Meryem ;

Guelcin, Ilhami ;

Goeksu, Sueleyman .

ARCHIV DER PHARMAZIE, 2014, 347 (01) :68-76

[4] Novel sulfamides as potential carbonic anhydrase isoenzymes inhibitors [J].

Akincioglu, Akin ;

Akbaba, Yusuf ;

Gocer, Hulya ;

Goksu, Suleyman ;

Gulcin, Ilhami ;

Supuran, Claudiu T. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (06) :1379-1385

[5] Carbonic anhydrase inhibitors: Benzenesulfonamides incorporating cyanoacrylamide moieties are low nanomolar/subnanomolar inhibitors of the tumor-associated isoforms IX and XII [J].

Alafeefy, Ahmed M. ;

Isik, Semra ;

Abdel-Aziz, Hatem A. ;

Ashour, Abdelkader E. ;

Vullo, Daniela ;

Al-Jaber, Nabila A. ;

Supuran, Claudiu T. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (06) :1396-1403

[6] Multiple Binding Modes of Inhibitors to Carbonic Anhydrases: How to Design Specific Drugs Targeting 15 Different Isoforms? [J].

Alterio, Vincenzo ;

Di Fiore, Anna ;

D'Ambrosio, Katia ;

Supuran, Claudiu T. ;

De Simone, Giuseppina .

CHEMICAL REVIEWS, 2012, 112 (08) :4421-4468

[7] Capsaicin: A Potent Inhibitor of Carbonic Anhydrase Isoenzymes [J].

Arabaci, Betul ;

Gulcin, Ilhami ;

Alwasel, Saleh .

MOLECULES, 2014, 19 (07) :10103-10114

[8] Effect of vitamin E on carbonic anhydrase enzyme activity in rainbow trout (Oncorhynchus mykiss) erythrocytes in vitro and in vivo [J].

Aras-Hisar, S ;

Hisar, O ;

Beydemir, S ;

Gülcin, I ;

Yanik, T .

ACTA VETERINARIA HUNGARICA, 2004, 52 (04) :413-422

[9] Adolescent male rats are less sensitive than adults to the anxiogenic and serotonin-releasing effects of fenfluramine [J].

Arrant, Andrew E. ;

Jemal, Hikma ;

Kuhn, Cynthia M. .

NEUROPHARMACOLOGY, 2013, 65 :213-222

[10] Synthesis of 4-[2-(3,4-dimethoxybenzyl)cyclopentyl]-1,2-dimethoxybenzene Derivatives and Evaluations of Their Carbonic Anhydrase Isoenzymes Inhibitory Effects [J].

Artunc, Tekin ;

Cetinkaya, Yasin ;

Gocer, Hulya ;

Gulcin, Ilhami ;

Menzek, Abdullah ;

Sahin, Ertan ;

Supuran, Claudiu T. .

CHEMICAL BIOLOGY & DRUG DESIGN, 2016, 87 (04) :594-607

← 1 2 3 4 5 6 7 8 9 10 →