Synthesis of (2E)-2-methyl-3-(4-([4-(quinolin-2-ylmethoxy)phenyl]sulfanyl)phenyl)prop-2-enoic acid (VUFB 20609) and 2-methyl-3-(4-([4-(quinolin-2-ylmethoxy)phenyl]sulfanyl)phenyl)propanoic acid (VUFB 20584) as potential antileukotrienic agents
Language English Country Great Britain, England Media print
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
15231044
DOI
10.1211/0022357023484
Knihovny.cz E-resources
- MeSH
- Leukotriene Antagonists chemical synthesis chemistry pharmacology MeSH
- Cell Death drug effects MeSH
- Quinolines chemical synthesis chemistry pharmacology MeSH
- Hydrogenation MeSH
- Platelet Aggregation Inhibitors chemical synthesis chemistry pharmacology MeSH
- Arachidonic Acid antagonists & inhibitors MeSH
- Humans MeSH
- Molecular Structure MeSH
- Cell Line, Tumor MeSH
- Stereoisomerism MeSH
- Sulfides chemical synthesis chemistry pharmacology MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- 2-methyl-3-(4-((4-(quinolin-2-ylmethoxy) phenyl)sulfanyl)phenyl)propanoic acid MeSH Browser
- 2-methyl-3-(4-((4-(quinolin-2-ylmethoxy)phenyl)sulfanyl)phenyl) prop-2-enoic acid MeSH Browser
- Leukotriene Antagonists MeSH
- Quinolines MeSH
- Platelet Aggregation Inhibitors MeSH
- Arachidonic Acid MeSH
- Sulfides MeSH
The syntheses of (2E)-2-methyl-3-(4-([4-(quinolin-2-ylmethoxy)phenyl]sulfanyl)phenyl) prop-2-enoic acid (VUFB 20609) and racemic 2-methyl-3-(4-([4-(quinolin-2-ylmethoxy) phenyl]sulfanyl)phenyl)propanoic acid (VUFB 20584) as new potential antileukotrienic drugs are described. Due to a low reactivity of the 4-substituted aryl bromides (coupling of the 4-substituted aryl bromides do not provide an activating functional group with 4-methoxybenzene-1-thiol), special conditions, in particular specific heterogeneous copper catalysts, were used. Catalytic hydrogenation of the conjugated double bond on Pd/C in the presence of the sulfanyl group is discussed. In-vitro cytotoxicity testing was performed using a microplate colorimetric acid phosphatase assay. Antiplatelet activity was evaluated using an in-vitro test in human platelet-rich plasma. Some substances inhibited arachidonic acid-induced platelet aggregation.
References provided by Crossref.org
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