Carbonic Anhydrases inhibitory effects of new benzenesulfonamides synthesized by using superacid chemistry

被引：67

作者：

Liu, Fei

Martin-Mingot, Agnes

Lecornue, F.

Jouannetaud, Marie-Paule

Maresca, Alfonso ^{[2
]}

Thibaudeau, Sebastien ^{[1
]}

Supuran, Claudiu T. ^{[2
]}

机构：

[1] Lab Synth & React Subst Nat, UMR 6514, F-86022 Poitiers, France

[2] Univ Florence, Lab Chim Bioinorgan, Florence, Italy

来源：

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY | 2012年 / 27卷 / 06期

关键词：

hypoxic tumors; superelectrophiles; fluorine chemistry; sultams; ISOZYME-IX; SULFONAMIDES; MOIETIES; ROUTE;

D O I：

10.3109/14756366.2011.638921

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：

A series of benzofused sultams and fluorinated benzenesulfonamides were synthesized in superacid HF/SbF5 from simple N-allylic derivatives. Almost all of these original compounds showed micromolar inhibitory activities against carbonic anhydrases I and II. The fluorinated derivatives inhibit better the tumor-associated isoforms IX and XII, and one of the tested compounds showed inhibition in the nanomolar range.

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收藏

页码：886 / 891

页数：6

相关论文

共 32 条

[1]

Alterio V., 2009, DRUG DESIGN ZINC ENZ, P73

[2] Crystal structure of the catalytic domain of the tumor-associated human carbonic anhydrase IX [J].

Alterio, Vincenzo ;

Hilvo, Mika ;

Di Fiore, Anna ;

Supuran, Claudiu T. ;

Pan, Peiwen ;

Parkkila, Seppo ;

Scaloni, Andrea ;

Pastorek, Jaromir ;

Pastorekova, Silvia ;

Pedone, Carlo ;

Scozzafava, Andrea ;

Monti, Simona Maria ;

De Simone, Giuseppina .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2009, 106 (38) :16233-16238

[3] Carbonic anhydrase inhibitors. Inhibition studies with anions and sulfonamides of a new cytosolic enzyme from the scleractinian coral Stylophora pistillata [J].

Bertucci, Anthony ;

Innocenti, Alessio ;

Scozzafava, Andrea ;

Tambutte, Sylvie ;

Zoccola, Didier ;

Supuran, Claudiu T. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (02) :710-714

[4] Conformational variability of different sulfonamide inhibitors with thienyl-acetamido moieties attributes to differential binding in the active site of cytosolic human carbonic anhydrase isoforms [J].

Biswas, Shyamasri ;

Aggarwal, Mayank ;

Guezel, Ozlen ;

Scozzafava, Andrea ;

McKenna, Robert ;

Supuran, Claudiu T. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (12) :3732-3738

[5] Synthesis of α-fluoro- and α,α-difluoro-benzenemethanesulfonamides:: new inhibitors of carbonic anhydrase [J].

Blackburn, GM ;

Türkmen, H .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (02) :225-226

[6] Indapamide-like benzenesulfonamides as inhibitors of carbonic anhydrases I, II, VII, and XIII [J].

Capkauskaite, Edita ;

Baranauskiene, Lina ;

Golovenko, Dmitrij ;

Manakova, Elena ;

Grazulis, Saulius ;

Tumkevicius, Sigitas ;

Matulis, Daumantas .

BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (21) :7357-7364

[7] Rearrangement or gem-difluorination of quinine and 9-epiquinine and their acetates in superacid [J].

Debarge, S ;

Thibaudeau, S ;

Violeau, B ;

Martin-Mingot, A ;

Jouannetaud, MP ;

Jacquesy, JC ;

Cousson, A .

TETRAHEDRON, 2005, 61 (08) :2065-2073

[8] Vinca alkaloids in superacidic media: A method for creating a new family of antitumor derivatives [J].

Fahy, J ;

Duflos, A ;

Ribet, JP ;

Jacquesy, JC ;

Berrier, C ;

Jouannetaud, MP ;

Zunino, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (36) :8576-8577

[9] Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives [J].

Ilies, MA ;

Vullo, D ;

Pastorek, J ;

Scozzafava, A ;

Ilies, M ;

Caproiu, MT ;

Pastorekova, S ;

Supuran, CT .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (11) :2187-2196

[10]

Jacquesy J-C, 2009, CARBOCATION CHEM, P359

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