Mercaptoamide-based non-hydroxamic acid type histone deacetylase inhibitors
The synthesis and histone deacetylase (HDAC) inhibitory activity of mercaptoamides 2 and 3 is described. Inhibitors of histone deacetylases (HDAC) are emerging as a promising class of anti-cancer agents. A mercaptoamide functionality was designed as a bidentate zinc chelator and incorporated into th...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2005-04, Vol.15 (8), p.1969-1972 |
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| container_end_page | 1972 |
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| container_issue | 8 |
| container_start_page | 1969 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 15 |
| creator | Anandan, Sampath-Kumar Ward, John S. Brokx, Richard D. Bray, Mark R. Patel, Dinesh V. Xiao, Xiao-Xi |
| description | The synthesis and histone deacetylase (HDAC) inhibitory activity of mercaptoamides
2 and
3 is described.
Inhibitors of histone deacetylases (HDAC) are emerging as a promising class of anti-cancer agents. A mercaptoamide functionality was designed as a bidentate zinc chelator and incorporated into the hydroxamic acid based SAHA (
1) scaffold in order to identify non-hydroxamate compounds as potential inhibitors of histone deacetylases. Two sets of mercaptoamides
2 and
3 with varying spacer length were synthesized and their HDAC inhibitory activity was evaluated. Low micromolar inhibition was observed for mercaptoamides
2e,
3b, and
3d. |
| doi_str_mv | 10.1016/j.bmcl.2005.02.075 |
| format | Article |
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2 and
3 is described.
Inhibitors of histone deacetylases (HDAC) are emerging as a promising class of anti-cancer agents. A mercaptoamide functionality was designed as a bidentate zinc chelator and incorporated into the hydroxamic acid based SAHA (
1) scaffold in order to identify non-hydroxamate compounds as potential inhibitors of histone deacetylases. Two sets of mercaptoamides
2 and
3 with varying spacer length were synthesized and their HDAC inhibitory activity was evaluated. Low micromolar inhibition was observed for mercaptoamides
2e,
3b, and
3d.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2005.02.075</identifier><identifier>PMID: 15808449</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Amides - chemistry ; Antineoplastic agents ; Biological and medical sciences ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - classification ; Enzyme Inhibitors - pharmacology ; General aspects ; Histone deacetylase inhibitor ; Histone Deacetylase Inhibitors ; Hydroxamic Acids - chemistry ; Medical sciences ; Mercaptoamides ; Non-hydroxamates ; Pharmacology. Drug treatments ; Sulfhydryl Compounds - chemistry</subject><ispartof>Bioorganic & medicinal chemistry letters, 2005-04, Vol.15 (8), p.1969-1972</ispartof><rights>2005 Elsevier Ltd</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c299t-c1f701c256e2872d221305bd20e57199ff227a1b22365fc231f8c512ecb56273</citedby><cites>FETCH-LOGICAL-c299t-c1f701c256e2872d221305bd20e57199ff227a1b22365fc231f8c512ecb56273</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X05002684$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16678890$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15808449$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Anandan, Sampath-Kumar</creatorcontrib><creatorcontrib>Ward, John S.</creatorcontrib><creatorcontrib>Brokx, Richard D.</creatorcontrib><creatorcontrib>Bray, Mark R.</creatorcontrib><creatorcontrib>Patel, Dinesh V.</creatorcontrib><creatorcontrib>Xiao, Xiao-Xi</creatorcontrib><title>Mercaptoamide-based non-hydroxamic acid type histone deacetylase inhibitors</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>The synthesis and histone deacetylase (HDAC) inhibitory activity of mercaptoamides
2 and
3 is described.
Inhibitors of histone deacetylases (HDAC) are emerging as a promising class of anti-cancer agents. A mercaptoamide functionality was designed as a bidentate zinc chelator and incorporated into the hydroxamic acid based SAHA (
1) scaffold in order to identify non-hydroxamate compounds as potential inhibitors of histone deacetylases. Two sets of mercaptoamides
2 and
3 with varying spacer length were synthesized and their HDAC inhibitory activity was evaluated. Low micromolar inhibition was observed for mercaptoamides
2e,
3b, and
3d.</description><subject>Amides - chemistry</subject><subject>Antineoplastic agents</subject><subject>Biological and medical sciences</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - classification</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>General aspects</subject><subject>Histone deacetylase inhibitor</subject><subject>Histone Deacetylase Inhibitors</subject><subject>Hydroxamic Acids - chemistry</subject><subject>Medical sciences</subject><subject>Mercaptoamides</subject><subject>Non-hydroxamates</subject><subject>Pharmacology. Drug treatments</subject><subject>Sulfhydryl Compounds - chemistry</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp90EGL1DAUwPEgLu64-gU8SC_urd2X1yRtwYssroorXvbgLaQvr0yGthmTjjjf3g4zsDdPgcfvPcJfiHcSKgnS3O2qfqKxQgBdAVbQ6BdiI5VRZa1AvxQb6AyUbad-XYvXOe8ApAKlXolrqVtoleo24vsPTuT2S3RT8Fz2LrMv5jiX26NP8e86pcJR8MVy3HOxDXmJMxeeHfFyHFddhHkb-rDElN-Iq8GNmd9e3hvx9PD56f5r-fjzy7f7T48lYdctJcmhAUmoDWPboEeUNejeI7BuZNcNA2LjZI9YGz0Q1nJoSUtk6rXBpr4Rt-ez-xR_HzgvdgqZeBzdzPGQrWkaMKjVCvEMKcWcEw92n8Lk0tFKsKeCdmdPBe2poAW0a8F16f3l-qGf2D-vXJKt4MMFuExuHJKbKeRnZ0zTth2s7uPZ8ZriT-BkMwWeiX1ITIv1MfzvH_8As_COxg</recordid><startdate>20050415</startdate><enddate>20050415</enddate><creator>Anandan, Sampath-Kumar</creator><creator>Ward, John S.</creator><creator>Brokx, Richard D.</creator><creator>Bray, Mark R.</creator><creator>Patel, Dinesh V.</creator><creator>Xiao, Xiao-Xi</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050415</creationdate><title>Mercaptoamide-based non-hydroxamic acid type histone deacetylase inhibitors</title><author>Anandan, Sampath-Kumar ; Ward, John S. ; Brokx, Richard D. ; Bray, Mark R. ; Patel, Dinesh V. ; Xiao, Xiao-Xi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c299t-c1f701c256e2872d221305bd20e57199ff227a1b22365fc231f8c512ecb56273</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Amides - chemistry</topic><topic>Antineoplastic agents</topic><topic>Biological and medical sciences</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - classification</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>General aspects</topic><topic>Histone deacetylase inhibitor</topic><topic>Histone Deacetylase Inhibitors</topic><topic>Hydroxamic Acids - chemistry</topic><topic>Medical sciences</topic><topic>Mercaptoamides</topic><topic>Non-hydroxamates</topic><topic>Pharmacology. Drug treatments</topic><topic>Sulfhydryl Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Anandan, Sampath-Kumar</creatorcontrib><creatorcontrib>Ward, John S.</creatorcontrib><creatorcontrib>Brokx, Richard D.</creatorcontrib><creatorcontrib>Bray, Mark R.</creatorcontrib><creatorcontrib>Patel, Dinesh V.</creatorcontrib><creatorcontrib>Xiao, Xiao-Xi</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Anandan, Sampath-Kumar</au><au>Ward, John S.</au><au>Brokx, Richard D.</au><au>Bray, Mark R.</au><au>Patel, Dinesh V.</au><au>Xiao, Xiao-Xi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Mercaptoamide-based non-hydroxamic acid type histone deacetylase inhibitors</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2005-04-15</date><risdate>2005</risdate><volume>15</volume><issue>8</issue><spage>1969</spage><epage>1972</epage><pages>1969-1972</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>The synthesis and histone deacetylase (HDAC) inhibitory activity of mercaptoamides
2 and
3 is described.
Inhibitors of histone deacetylases (HDAC) are emerging as a promising class of anti-cancer agents. A mercaptoamide functionality was designed as a bidentate zinc chelator and incorporated into the hydroxamic acid based SAHA (
1) scaffold in order to identify non-hydroxamate compounds as potential inhibitors of histone deacetylases. Two sets of mercaptoamides
2 and
3 with varying spacer length were synthesized and their HDAC inhibitory activity was evaluated. Low micromolar inhibition was observed for mercaptoamides
2e,
3b, and
3d.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>15808449</pmid><doi>10.1016/j.bmcl.2005.02.075</doi><tpages>4</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2005-04, Vol.15 (8), p.1969-1972 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Amides - chemistry Antineoplastic agents Biological and medical sciences Enzyme Inhibitors - chemistry Enzyme Inhibitors - classification Enzyme Inhibitors - pharmacology General aspects Histone deacetylase inhibitor Histone Deacetylase Inhibitors Hydroxamic Acids - chemistry Medical sciences Mercaptoamides Non-hydroxamates Pharmacology. Drug treatments Sulfhydryl Compounds - chemistry |
| title | Mercaptoamide-based non-hydroxamic acid type histone deacetylase inhibitors |
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