Design, synthesis and biological activity of selective hCAs inhibitors based on 2-(benzylsulfinyl)benzoic acid scaffold.
Carbonic anhydrase inhibitor
carboxylic acid
molecular modelling
sulfoxide enantioseparation
Journal
Journal of enzyme inhibition and medicinal chemistry
ISSN: 1475-6374
Titre abrégé: J Enzyme Inhib Med Chem
Pays: England
ID NLM: 101150203
Informations de publication
Date de publication:
Dec 2019
Dec 2019
Historique:
entrez:
13
8
2019
pubmed:
14
8
2019
medline:
27
8
2019
Statut:
ppublish
Résumé
A large library of derivatives based on the scaffold of 2-(benzylsulfinyl)benzoic acid were synthesised and tested as atypical inhibitors against four different isoforms of human carbonic anhydrase (hCA I, II, IX and XII, EC 4.2.1.1). The exploration of the chemical space around the main functional groups led to the discovery of selective hCA IX inhibitors in the micromolar/nanomolar range, thus establishing robust structure-activity relationships within this versatile scaffold. HPLC separation of some selected chiral compounds and biological evaluation of the corresponding enantiomers was performed along with molecular modelling studies on the most active derivatives.
Identifiants
pubmed: 31401897
doi: 10.1080/14756366.2019.1651315
pmc: PMC6713143
doi:
Substances chimiques
Carbonic Anhydrase Inhibitors
0
Isoenzymes
0
Benzoic Acid
8SKN0B0MIM
Carbonic Anhydrases
EC 4.2.1.1
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
1400-1413Références
J Pharmacol Toxicol Methods. 2001 Sep-Oct;46(2):61-71
pubmed: 12481843
J Comput Chem. 2008 Jul 30;29(10):1693-8
pubmed: 18307169
Proteins. 2009 Apr;75(1):187-205
pubmed: 18814299
Eur J Med Chem. 2011 Jul;46(7):2880-94
pubmed: 21524830
J Org Chem. 2011 Sep 2;76(17):7040-7
pubmed: 21739975
Nat Rev Cancer. 2011 Aug 11;11(9):671-7
pubmed: 21833026
Nat Rev Drug Discov. 2011 Sep 16;10(10):767-77
pubmed: 21921921
Surg Oncol. 2012 Sep;21(3):172-7
pubmed: 21963199
Chem Rev. 2012 Aug 8;112(8):4421-68
pubmed: 22607219
J Med Chem. 2012 Jun 14;55(11):5591-600
pubmed: 22621623
Nat Rev Cancer. 2013 Sep;13(9):611-23
pubmed: 23969692
J Enzyme Inhib Med Chem. 2015 Feb;30(1):114-8
pubmed: 24666302
Chem Commun (Camb). 2015;51(2):302-5
pubmed: 25407638
J Org Chem. 2015 Apr 3;80(7):3688-94
pubmed: 25751087
Molecules. 2015 Mar 31;20(4):5667-79
pubmed: 25838170
Bioorg Med Chem. 2015 Jul 1;23(13):2975-81
pubmed: 26007302
Chemistry. 2016 Jan 4;22(1):97-100
pubmed: 26507456
J Enzyme Inhib Med Chem. 2016;31(3):345-60
pubmed: 26619898
Bioorg Med Chem. 2016 Mar 1;24(5):1095-105
pubmed: 26810710
ChemMedChem. 2016 Aug 19;11(16):1695-9
pubmed: 27377568
J Chromatogr A. 2016 Oct 7;1467:221-227
pubmed: 27461921
Expert Opin Drug Discov. 2017 Jan;12(1):61-88
pubmed: 27783541
J Enzyme Inhib Med Chem. 2017 Dec;32(1):51-59
pubmed: 27784170
Food Chem. 2017 Apr 15;221:855-863
pubmed: 27979284
J Pharm Biomed Anal. 2017 May 30;139:1-7
pubmed: 28258982
J Pharm Biomed Anal. 2017 Jun 5;140:38-44
pubmed: 28340473
J Chromatogr A. 2017 May 26;1499:140-148
pubmed: 28416216
J Enzyme Inhib Med Chem. 2017 Dec;32(1):1079-1090
pubmed: 28783982
Food Chem Toxicol. 2018 Feb;112:441-447
pubmed: 28807875
J Enzyme Inhib Med Chem. 2017 Dec;32(1):1174-1182
pubmed: 28891347
J Enzyme Inhib Med Chem. 2017 Dec;32(1):1274-1281
pubmed: 28965419
Molecules. 2017 Dec 09;22(12):null
pubmed: 29232847
J Enzyme Inhib Med Chem. 2018 Dec;33(1):485-495
pubmed: 29390912
Future Med Chem. 2018 Mar 1;10(5):561-573
pubmed: 29478330
Oncoimmunology. 2018 Mar 26;7(7):e1445452
pubmed: 29900055
Expert Opin Ther Pat. 2018 Oct;28(10):745-754
pubmed: 29973089
J Enzyme Inhib Med Chem. 2018 Dec;33(1):1137-1149
pubmed: 30001631
J Enzyme Inhib Med Chem. 2018 Dec;33(1):1150-1159
pubmed: 30001665
Expert Opin Ther Pat. 2018 Oct;28(10):729-740
pubmed: 30074415
Expert Opin Ther Pat. 2018 Oct;28(10):713-721
pubmed: 30175635
Expert Opin Ther Pat. 2018 Oct;28(10):709-712
pubmed: 30217119
J Enzyme Inhib Med Chem. 2018 Dec;33(1):1430-1443
pubmed: 30220229
Expert Opin Investig Drugs. 2018 Dec;27(12):963-970
pubmed: 30426805
J Enzyme Inhib Med Chem. 2019 Dec;34(1):189-195
pubmed: 30734607
J Enzyme Inhib Med Chem. 2019 Dec;34(1):703-711
pubmed: 30810431
J Enzyme Inhib Med Chem. 2019 Dec;34(1):1051-1061
pubmed: 31074307
J Biol Chem. 1971 Apr 25;246(8):2561-73
pubmed: 4994926