Document Detail

Alkylsquarates as key intermediates for the rapid preparation of original drug-inspired compounds.
MedLine Citation:
PMID:  18473739     Owner:  NLM     Status:  MEDLINE    
Many natural privileged scaffolds contain a basic nitrogen atom, which often is a key element of pharmacophore and a chemically reactive centre as well. In our ongoing research program devoted to the design of targeted libraries based on acidic templates, we developed methods to convert privileged basic compounds -like natural alkaloids or drugs into acidic compounds. This conversion led to a profound alteration of the pharmacophore, without changing the overall shape and lipophilicity of the molecule. We expect such modifications to generate unexpected biological activities. Recently, we focused on derivatives of squaric acid, a vinylogous carboxylic acid. Two series were studied. First we describe a new, selective parallel synthesis of squaramic acids from a dissymmetric diester (3-tert-butoxy-4-ethoxy-cyclobut-3-en-1,2-dione). This efficient procedure avoids the synthesis of the undesired squaramides. Secondly we describe a microplate parallel synthesis (15 micromol-scale) of squaric acid hydroxamate amides from a squaric hydroxamate ester.
Julie Charton; Lise Charruault; Rebecca Deprez-Poulain; Benoit Deprez
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Combinatorial chemistry & high throughput screening     Volume:  11     ISSN:  1386-2073     ISO Abbreviation:  Comb. Chem. High Throughput Screen.     Publication Date:  2008 May 
Date Detail:
Created Date:  2008-05-13     Completed Date:  2008-07-22     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9810948     Medline TA:  Comb Chem High Throughput Screen     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  294-303     Citation Subset:  IM    
INSERM U761 Biostructures and Drug Discovery, F-59006 Lille, France.
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MeSH Terms
Amines / chemical synthesis,  chemistry
Chelating Agents / chemical synthesis,  chemistry
Chemistry, Pharmaceutical / methods
Combinatorial Chemistry Techniques / methods*
Cyclobutanes / chemistry*
Enzyme Inhibitors / chemical synthesis,  chemistry
Esters / chemistry
Hydroxamic Acids / chemistry
Molecular Structure
Pharmaceutical Preparations / chemical synthesis,  chemistry*
Piperidines / chemistry
Small Molecule Libraries / chemical synthesis,  chemistry*
Zinc / chemistry
Reg. No./Substance:
0/Amines; 0/Chelating Agents; 0/Cyclobutanes; 0/Enzyme Inhibitors; 0/Esters; 0/Hydroxamic Acids; 0/Pharmaceutical Preparations; 0/Piperidines; 0/Small Molecule Libraries; 0/diethyl squarate; 2892-51-5/squaric acid; 7440-66-6/Zinc

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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