Reactions of amino, aminomethyl tetralins and benzyl alcohol with chlorosulphonyl isocyanate (CSI) afforded sulphamoyl carbamates. The sulphamoyl carbamates were converted to sulphamides by palladium-catalysed hydrogenolysis. Sulphonamides were synthesized from the reactions of amines with MeSO2 Cl. Inhibition of human (h) carbonic anhydrase (CA) isoenzymes (hCA I, hCA II) and acetylcholine esterase (AChE) was investigated with the synthesized compounds. hCA I and hCA II were inhibited in the low micromolar or sub-micromolar range. The Ki values were in the range of 0.91-9.56 µM against hCA I and of 3.70-27.88 µM against hCA II. Sulphamides 11-13 and sulphonamides 14-16 had moderate inhibition capacity toward AChE. These findings suggest the novel sulphamides 11-13 and sulphonamides 14-16 as AChE and CA isoenzyme inhibitory agents.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/ardp.201300273 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A structure-based approach towards the identification of novel antichagasic compounds: carbonic anhydrase inhibitors.
J Enzyme Inhib Med Chem
December 2020
Laboratory of Bioactive Research and Development (LIDeB), Medicinal Chemistry, Department of Biological Sciences, Faculty of Exact Sciences, National University of La Plata, Buenos Aires , Argentina.
carbonic anhydrase (CA) has recently emerged as an interesting target for the design of new compounds to treat Chagas disease. In this study we report the results of a structure-based virtual screening campaign to identify novel and selective CA inhibitors. The combination of properly validated computational methodologies such as comparative modelling, molecular dynamics and docking simulations allowed us to find high potency hits, with K values in the nanomolar range.
View Article and Find Full Text PDFSynthesis, molecular docking and biological evaluation of 1-phenylsulphonyl-2-(1-methylindol-3-yl)-benzimidazole derivatives as novel potential tubulin assembling inhibitors.
Chem Biol Drug Des
July 2017
State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, China.
A series of new 1-phenylsulphonyl-2-(1-methylindol-3-yl)-benzimidazole derivatives were designed, synthesized and evaluated as potential inhibitors of tubulin polymerization and anthropic cancer cell lines. Among them, compound 33 displayed the most potent tubulin polymerization inhibitory activity in vitro (IC = 1.41 μM) and strong antiproliferative activities against A549, Hela, HepG2 and MCF-7 cell lines in vitro with GI value of 1.
View Article and Find Full Text PDFNovel sulphamides and sulphonamides incorporating the tetralin scaffold as carbonic anhydrase and acetylcholine esterase inhibitors.
Arch Pharm (Weinheim)
January 2014
Central Researching Laboratory, Agri Ibrahim Cecen University, Agri, Turkey; Faculty of Science, Department of Chemistry, Atatürk University, Erzurum, Turkey.
Reactions of amino, aminomethyl tetralins and benzyl alcohol with chlorosulphonyl isocyanate (CSI) afforded sulphamoyl carbamates. The sulphamoyl carbamates were converted to sulphamides by palladium-catalysed hydrogenolysis. Sulphonamides were synthesized from the reactions of amines with MeSO2 Cl.
View Article and Find Full Text PDFStructure-based drug discovery of carbonic anhydrase inhibitors.
J Enzyme Inhib Med Chem
December 2012
Università degli Studi di Firenze, Polo Scientifico, Laboratorio di Chimica Bioinorganica, Via della Lastruccia, Sesto Fiorentino, Florence, Italy.
Inhibition of the metalloenzyme carbonic anhydrase (CA; EC 4.2.1.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!