Synthesis and Aromatase Inhibitory Activity of Novel Pyridine-Containing Isoflavones
Aromatase, a cytochrome P450 hemoprotein that is responsible for estrogen biosynthesis by conversion of androgens into estrogens, has been an attractive target in the treatment of hormone-dependent breast cancer. As a result, a number of synthetic steroidal or nonsteroidal aromatase inhibitors have...
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| Veröffentlicht in: | Journal of medicinal chemistry 2004-07, Vol.47 (16), p.4032-4040 |
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| container_title | Journal of medicinal chemistry |
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| creator | Kim, Young-Woo Hackett, John C Brueggemeier, Robert W |
| description | Aromatase, a cytochrome P450 hemoprotein that is responsible for estrogen biosynthesis by conversion of androgens into estrogens, has been an attractive target in the treatment of hormone-dependent breast cancer. As a result, a number of synthetic steroidal or nonsteroidal aromatase inhibitors have been successfully developed. In addition, there are several classes of natural products that exert potent activities in aromatase inhibition, with the flavonoids being most prominent. Previous studies have exploited flavone and flavanone scaffolds for the development of new aromatase inhibitors. In this paper, we describe the design, synthesis, and biological evaluation of a novel series of 2-(4‘-pyridylmethyl)thioisoflavones as the first example of synthetic isoflavone-based aromatase inhibitors. |
| doi_str_mv | 10.1021/jm0306024 |
| format | Article |
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As a result, a number of synthetic steroidal or nonsteroidal aromatase inhibitors have been successfully developed. In addition, there are several classes of natural products that exert potent activities in aromatase inhibition, with the flavonoids being most prominent. Previous studies have exploited flavone and flavanone scaffolds for the development of new aromatase inhibitors. In this paper, we describe the design, synthesis, and biological evaluation of a novel series of 2-(4‘-pyridylmethyl)thioisoflavones as the first example of synthetic isoflavone-based aromatase inhibitors.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm0306024</identifier><identifier>PMID: 15267241</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Antineoplastic agents ; Aromatase - chemistry ; Aromatase - metabolism ; Aromatase Inhibitors ; Biological and medical sciences ; Female ; General aspects ; Humans ; In Vitro Techniques ; Isoflavones - chemical synthesis ; Isoflavones - chemistry ; Isoflavones - pharmacology ; Kinetics ; Medical sciences ; Microsomes - metabolism ; Pharmacology. Drug treatments ; Placenta - ultrastructure ; Pyridines - chemical synthesis ; Pyridines - chemistry ; Pyridines - pharmacology ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 2004-07, Vol.47 (16), p.4032-4040</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-c99c3024e56c0aaa04b96bdcf68adcc0f37cdf1ed982e88667abf7a8be987d13</citedby><cites>FETCH-LOGICAL-a445t-c99c3024e56c0aaa04b96bdcf68adcc0f37cdf1ed982e88667abf7a8be987d13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm0306024$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm0306024$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15965968$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15267241$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kim, Young-Woo</creatorcontrib><creatorcontrib>Hackett, John C</creatorcontrib><creatorcontrib>Brueggemeier, Robert W</creatorcontrib><title>Synthesis and Aromatase Inhibitory Activity of Novel Pyridine-Containing Isoflavones</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Aromatase, a cytochrome P450 hemoprotein that is responsible for estrogen biosynthesis by conversion of androgens into estrogens, has been an attractive target in the treatment of hormone-dependent breast cancer. As a result, a number of synthetic steroidal or nonsteroidal aromatase inhibitors have been successfully developed. In addition, there are several classes of natural products that exert potent activities in aromatase inhibition, with the flavonoids being most prominent. Previous studies have exploited flavone and flavanone scaffolds for the development of new aromatase inhibitors. In this paper, we describe the design, synthesis, and biological evaluation of a novel series of 2-(4‘-pyridylmethyl)thioisoflavones as the first example of synthetic isoflavone-based aromatase inhibitors.</description><subject>Antineoplastic agents</subject><subject>Aromatase - chemistry</subject><subject>Aromatase - metabolism</subject><subject>Aromatase Inhibitors</subject><subject>Biological and medical sciences</subject><subject>Female</subject><subject>General aspects</subject><subject>Humans</subject><subject>In Vitro Techniques</subject><subject>Isoflavones - chemical synthesis</subject><subject>Isoflavones - chemistry</subject><subject>Isoflavones - pharmacology</subject><subject>Kinetics</subject><subject>Medical sciences</subject><subject>Microsomes - metabolism</subject><subject>Pharmacology. Drug treatments</subject><subject>Placenta - ultrastructure</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - chemistry</subject><subject>Pyridines - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M1rFDEYBvAgFrtWD_4DMhcFD1PzMZOZOS7r10KphV0UvIR3MonNOpPUvNml898b2aX1IARyyC8PDw8hrxi9ZJSz97uJCiopr56QBas5LauWVk_JglLOSy65OCfPEXeUUsG4eEbOM5INr9iCbDezT7cGHRbgh2IZwwQJ0BRrf-t6l0Kci6VO7uDSXARbXIeDGYubObrBeVOugk_gvPM_izUGO8IheIMvyJmFEc3L031Btp8-bldfyquvn9er5VUJVVWnUnedFrm1qaWmAECrvpP9oK1sYdCaWtHowTIzdC03bStlA71toO1N1zYDExfk7TH2Lobfe4NJTQ61GUfwJuxR5Q9CCCkzfHeEOgbEaKy6i26COCtG1d8F1cOC2b4-he77yQyP8jRZBm9OAFDDaCN47fAf18l82uzKo3OYzP3DO8RfKvdqarW92ajNB_b9R824-vaYCxrVLuyjz9P9p-AfLzOUcQ</recordid><startdate>20040729</startdate><enddate>20040729</enddate><creator>Kim, Young-Woo</creator><creator>Hackett, John C</creator><creator>Brueggemeier, Robert W</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>20040729</creationdate><title>Synthesis and Aromatase Inhibitory Activity of Novel Pyridine-Containing Isoflavones</title><author>Kim, Young-Woo ; Hackett, John C ; Brueggemeier, Robert W</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-c99c3024e56c0aaa04b96bdcf68adcc0f37cdf1ed982e88667abf7a8be987d13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Antineoplastic agents</topic><topic>Aromatase - chemistry</topic><topic>Aromatase - metabolism</topic><topic>Aromatase Inhibitors</topic><topic>Biological and medical sciences</topic><topic>Female</topic><topic>General aspects</topic><topic>Humans</topic><topic>In Vitro Techniques</topic><topic>Isoflavones - chemical synthesis</topic><topic>Isoflavones - chemistry</topic><topic>Isoflavones - pharmacology</topic><topic>Kinetics</topic><topic>Medical sciences</topic><topic>Microsomes - metabolism</topic><topic>Pharmacology. Drug treatments</topic><topic>Placenta - ultrastructure</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - chemistry</topic><topic>Pyridines - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Young-Woo</creatorcontrib><creatorcontrib>Hackett, John C</creatorcontrib><creatorcontrib>Brueggemeier, Robert W</creatorcontrib><collection>Istex</collection><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>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Young-Woo</au><au>Hackett, John C</au><au>Brueggemeier, Robert W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Aromatase Inhibitory Activity of Novel Pyridine-Containing Isoflavones</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2004-07-29</date><risdate>2004</risdate><volume>47</volume><issue>16</issue><spage>4032</spage><epage>4040</epage><pages>4032-4040</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>Aromatase, a cytochrome P450 hemoprotein that is responsible for estrogen biosynthesis by conversion of androgens into estrogens, has been an attractive target in the treatment of hormone-dependent breast cancer. As a result, a number of synthetic steroidal or nonsteroidal aromatase inhibitors have been successfully developed. In addition, there are several classes of natural products that exert potent activities in aromatase inhibition, with the flavonoids being most prominent. Previous studies have exploited flavone and flavanone scaffolds for the development of new aromatase inhibitors. 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| language | eng |
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| subjects | Antineoplastic agents Aromatase - chemistry Aromatase - metabolism Aromatase Inhibitors Biological and medical sciences Female General aspects Humans In Vitro Techniques Isoflavones - chemical synthesis Isoflavones - chemistry Isoflavones - pharmacology Kinetics Medical sciences Microsomes - metabolism Pharmacology. Drug treatments Placenta - ultrastructure Pyridines - chemical synthesis Pyridines - chemistry Pyridines - pharmacology Structure-Activity Relationship |
| title | Synthesis and Aromatase Inhibitory Activity of Novel Pyridine-Containing Isoflavones |
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