Novel sulfamides as potential carbonic anhydrase isoenzymes inhibitors

被引:115
|
作者
Akincioglu, Akin [1 ]
Akbaba, Yusuf [1 ]
Gocer, Hulya [2 ]
Goksu, Suleyman [1 ]
Gulcin, Ilhami [1 ]
Supuran, Claudiu T. [3 ]
机构
[1] Ataturk Univ, Dept Chem, Fac Sci, TR-25240 Erzurum, Turkey
[2] Ibrahim Cecen Univ Agri, Cent Researching Lab, TR-04200 Agri, Turkey
[3] Univ Florence, Dipartimento Sci Farmaceut, I-50019 Florence, Italy
关键词
Aminoindane; Aminotetralin; Sulfamide; Carbonic anhydrase; Inhibitors; ERYTHROCYTES IN-VITRO; ISOZYMES I; ENZYME-ACTIVITY; DANTROLENE; LACTOPEROXIDASE; PURIFICATION; MELATONIN; PROPOFOL; SERIES; XII;
D O I
10.1016/j.bmc.2013.01.019
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
Sulfamides represent an important class of biologically active compounds. A series of novel sulfamides were synthesized from 1-aminoindanes, 1-aminotetralin, 2-aminoindanes and 2-aminotetralin via the reactions of free amines, benzyl alcohol and chlorosulfonyl isocyanate (CSI) followed by hydrogenolysis of the obtained sulfamoylcarbamates. Carbonic anhydrase (CA, EC 4.2.1.1) inhibitory effects of the new sulfamides have been investigated. The human (h) isozymes hCA I and hCA II have been investigated in this study by using an esterase assay with 4-nitrophenyl acetate as substrate. The new sulfamides showed inhibition constants in the micro-submicromolar range, with one compound (N-(indane-1-yl) sulfamide) showing a K-i of 0.45 mu M against hCA I and of 1.07 mu M against hCA II. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1379 / 1385
页数:7
相关论文
共 50 条
  • [41] DEPRESSION OF CHLORIDE TRANSPORT BY CARBONIC ANHYDRASE INHIBITORS IN ABSENCE OF CARBONIC ANHYDRASE
    KITAHARA, S
    FOX, KR
    HOGBEN, CAM
    NATURE, 1967, 214 (5090) : 836 - &
  • [42] Safety of carbonic anhydrase inhibitors
    Swenson, Erik R.
    EXPERT OPINION ON DRUG SAFETY, 2014, 13 (04) : 459 - 472
  • [43] ENDOGENOUS INHIBITORS OF CARBONIC ANHYDRASE
    TAPPAN, DV
    BOYDEN, HM
    JACEY, MJ
    FEDERATION PROCEEDINGS, 1962, 21 (02) : 247 - &
  • [44] Antiobesity carbonic anhydrase inhibitors
    De Simone, Giuseppina
    Supuran, Claudiu T.
    CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2007, 7 (09) : 879 - 884
  • [45] CARBONIC-ANHYDRASE INHIBITORS
    PREISIG, PA
    TOTO, RD
    ALPERN, RJ
    RENAL PHYSIOLOGY AND BIOCHEMISTRY, 1987, 10 (3-4): : 136 - 159
  • [46] Diversely substituted sulfamides for fragment-based drug discovery of carbonic anhydrase inhibitors: synthesis and inhibitory profile
    Sharonova, Tatiana
    Zhmurov, Petr
    Kalinin, Stanislav
    Nocentini, Alessio
    Angeli, Andrea
    Ferraroni, Marta
    Korsakov, Mikhail
    Supuran, Claudiu T.
    Krasavin, Mikhail
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2022, 37 (01) : 857 - 865
  • [47] Carbonic anhydrase inhibitors: an editorial
    Supuran, Claudiu T.
    EXPERT OPINION ON THERAPEUTIC PATENTS, 2013, 23 (06) : 677 - 679
  • [48] Hypoxia-Targeting Carbonic Anhydrase IX Inhibitors by a New Series of Nitroimidazole-Sulfonamides/Sulfamides/Sulfamates
    Rami, Marouan
    Dubois, Ludwig
    Parvathaneni, Nanda-Kumar
    Alterio, Vincenzo
    van Kuijk, Simon J. A.
    Monti, Simona Maria
    Lambin, Philippe
    De Simone, Giuseppina
    Supuran, Claudiu T.
    Winum, Jean-Yves
    JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (21) : 8512 - 8520
  • [49] Binding thermodynamics of novel selective inhibitors of Carbonic Anhydrase IX
    Timm, D. D.
    Zubriene, A.
    Baranauskiene, L.
    Morkunaite, V.
    Smirnoviene, J.
    Matulis, D.
    EUROPEAN BIOPHYSICS JOURNAL WITH BIOPHYSICS LETTERS, 2015, 44 : S64 - S64
  • [50] Discovery and Characterization of Novel Selective Inhibitors of Carbonic Anhydrase IX
    Dudutiene, Virginija
    Matuliene, Jurgita
    Smirnov, Alexey
    Timm, David D.
    Zubriene, Asta
    Baranauskiene, Lina
    Morkunaite, Vaida
    Smirnoviene, Joana
    Michailoviene, Vilma
    Juozapaitiene, Vaida
    Mickeviciute, Aurelija
    Kazokaite, Justina
    Baksyte, Sandra
    Kasiliauskaite, Aiste
    Jachno, Jelena
    Revuckiene, Jurgita
    Kisonaite, Migle
    Pilipuityte, Vilma
    Ivanauskaite, Egle
    Milinaviciute, Goda
    Smirnovas, Vytautas
    Petrikaite, Vilma
    Kairys, Visvaldas
    Petrauskas, Vytautas
    Norvaisas, Povilas
    Linge, Darius
    Gibieza, Paulius
    Capkauskaite, Edita
    Zaksauskas, Audrius
    Kazlauskas, Egidijus
    Manakova, Elena
    Grazulis, Saulius
    Ladbury, John E.
    Matulis, Daumantas
    JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (22) : 9435 - 9446