Thioether benzenesulfonamide inhibitors of carbonic anhydrases II and IV: Structure-based drug design, synthesis, and biological evaluation

被引：41
|
作者：
Vernier, William [1 ]
Chong, Wesley [1 ]
Rewolinski, David [1 ]
Greasley, Samantha [1 ]
Pauly, Thomas [1 ]
Shaw, Morena [1 ]
Dinh, Dac [1 ]
Ferre, Rose Ann [1 ]
Nukui, Seiji [1 ]
Ornelas, Martha [1 ]
Reyner, Eric [1 ]
机构：
[1] Pfizer Global Res & Dev, La Jolla Labs, San Diego, CA 92121 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2010年 / 18卷 / 09期
关键词：
Carbonic anhydrase; Thioether benzenesulfonamide; Glaucoma; DORZOLAMIDE; PERMEABILITY; TIMOLOL; ACETAZOLAMIDE; SULFONAMIDES; DERIVATIVES; REFINEMENT; SIMULATION; CHEMISTRY; BINDING;
D O I：
10.1016/j.bmc.2010.03.014
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 novel series of potent thioether benzenesulfonamide inhibitors of carbonic anhydrases II and IV was discovered using structure-based drug design. Synthesis, structure-activity relationship, and optimization of physicochemical properties are described. Low nanomolar potency was achieved, and selected compounds with improved thermodynamic solubility showed promising in vitro inhibition of carbonic anhydrase activity in rabbit iris ciliary body homogenate. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3307 / 3319
页数：13
相关论文
共 50 条
  • [31] Structure-based design,synthesis,and biological evaluation of novel pyrimidinone derivatives as PDE9 inhibitors
    Xu-Nian Wu
    Ya-Dan Huang
    Jin-Xuan Li
    Yan-Fa Yu
    Qian Zhou
    Chen Zhang
    Yinuo Wu
    Hai-Bin Luo
    ActaPharmaceuticaSinicaB, 2018, 8 (04) : 615 - 628
  • [32] Novel benzofuran-based sulphonamides as selective carbonic anhydrases IX and XII inhibitors: synthesis and in vitro biological evaluation
    Abdelrahman, Mohamed A.
    Eldehna, Wagdy M.
    Nocentini, Alessio
    Ibrahim, Hany S.
    Almahli, Hadia
    Abdel-Aziz, Hatem A.
    Abou-Seri, Sahar M.
    Supuran, Claudiu T.
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2020, 35 (01) : 298 - 305
  • [33] Structure-based design, synthesis, and in vitro evaluation of nonpepticlic neprilysin inhibitors
    Sahli, S
    Stump, B
    Welti, T
    Blum-Kaelin, D
    Aebi, JD
    Oefner, C
    Böhm, JH
    Diederich, F
    CHEMBIOCHEM, 2004, 5 (07) : 996 - 1000
  • [34] Structure-based design, synthesis, and evaluation of amyloid fibril inhibitors.
    Kelly, JW
    Petrassi, HM
    Oza, V
    Purkey, H
    Koepf, E
    Raman, P
    Klabunde, T
    Sacchettini, J
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U201 - U201
  • [35] Synthesis of Novel Selenides Bearing Benzenesulfonamide Moieties as Carbonic Anhydrase I, II, IV, VII, and IX Inhibitors
    Angeli, Andrea
    Tanini, Damiano
    Capperucci, Antonella
    Supuran, Claudiu T.
    ACS MEDICINAL CHEMISTRY LETTERS, 2017, 8 (12): : 1213 - 1217
  • [36] Structure-based drug design and the evaluation of irreversible HCV-protease inhibitors
    Qiao, Lixin
    Niu, Deqiang
    Zhu, Zhendong
    Labenski, Matt
    Hagel, Margit
    St Martin, Thia
    Sheet, Michael
    Bernard, Hugues
    Nacht, Mariana
    Westlin, Willian
    Petter, Russell
    Singh, Juswinder
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [37] ITERATIVE PROTEIN STRUCTURE-BASED DRUG DESIGN AND SYNTHESIS OF HIV PROTEASE INHIBITORS
    KALISH, V
    KALDOR, S
    SHETTY, B
    TATLOCK, J
    DAVIES, J
    HAMMOND, M
    DRESSMAN, B
    FRITZ, J
    APPELT, K
    REICH, S
    MUSICK, L
    WU, BW
    SU, K
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1995, 30 : S201 - S214
  • [38] PROTEIN STRUCTURE-BASED DRUG DESIGN AND SYNTHESIS OF NONPEPTIDIC HIV PROTEASE INHIBITORS
    TATLOCK, JH
    KALISH, VJ
    DAVIES, J
    APPELT, K
    REICH, S
    MUSICK, L
    WU, B
    KALDOR, S
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 120 - MEDI
  • [39] PROTEIN STRUCTURE-BASED DRUG DESIGN AND SYNTHESIS OF NONPEPTIDIC HIV PROTEASE INHIBITORS
    GAJDA, C
    DOMAGALA, J
    TAIT, B
    HAGEN, S
    TUMINO, P
    FERGUSON, D
    PAVLOVSKY, A
    RUBIN, J
    LUNNEY, E
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 210 : 21 - MEDI
  • [40] Hypoxia-Activated Prodrug Derivatives of Carbonic Anhydrase Inhibitors in Benzenesulfonamide Series: Synthesis and Biological Evaluation
    Anduran, Emilie
    Aspatwar, Ashok
    Parvathaneni, Nanda-Kumar
    Suylen, Dennis
    Bua, Silvia
    Nocentini, Alessio
    Parkkila, Seppo
    Supuran, Claudiu T.
    Dubois, Ludwig
    Lambin, Philippe
    Winum, Jean-Yves
    MOLECULES, 2020, 25 (10):
12345