Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistry
A series of 4-[(triazolyl)methoxy]phenyl analogs of the phenoxyphenyl-substituted thiirane SB-3CT 1 was evaluated for its ability to inhibit gelatinases, members of the matrix metalloproteinase family of enzymes. The triazole segment of these inhibitors was assembled using the Meldal-Sharpless coppe...
| Authors: | , , , , |
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| Format: | article |
| Status: | Published version |
| Publication Date: | 2011 |
| Country: | Argentina |
| Institution: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repository: | CONICET Digital (CONICET) |
| Language: | English |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/129195 |
| Online Access: | http://hdl.handle.net/11336/129195 |
| Access Level: | Open access |
| Keyword: | CUAAC CLICK CHEMISTRY GELATINASE INHIBITOR MMP THIIRANE https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Summary: | A series of 4-[(triazolyl)methoxy]phenyl analogs of the phenoxyphenyl-substituted thiirane SB-3CT 1 was evaluated for its ability to inhibit gelatinases, members of the matrix metalloproteinase family of enzymes. The triazole segment of these inhibitors was assembled using the Meldal-Sharpless copper-catalyzed Huisgen dipolar cycloaddition of an azide and a terminal alkyne. While these triazole derivatives possessed fair activity as gelatinase inhibitors, an intermediate used in the dipolar cycloaddition, 4-(propargyloxy)phenyl derivative 2, showed very good activity (<50% inhibitory activity following a 3 h pre-incubation of 2 at a concentration of 3 μM) as an inhibitor of human matrix metalloproteinase-2. |
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