Synthesis of Abyssinone II and related compounds as potential chemopreventive agents
A facile and efficient approach to the synthesis of prenylated flavonoids as potential chemopreventive agents has been described. This features the synthesis of prenyl halide, prenylation of p-hydroxybenzaldehyde, formation of prenylated polyhydroxychalcone and cyclization of prenylated polyhydroxyc...
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| Veröffentlicht in: | European journal of medicinal chemistry 2006-02, Vol.41 (2), p.263-267 |
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| container_title | European journal of medicinal chemistry |
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| creator | Moriarty, Robert M. Grubjesic, Simonida Surve, Bhushan C. Chandersekera, Susantha N. Prakash, Om Naithani, Rajesh |
| description | A facile and efficient approach to the synthesis of prenylated flavonoids as potential chemopreventive agents has been described. This features the synthesis of prenyl halide, prenylation of
p-hydroxybenzaldehyde, formation of prenylated polyhydroxychalcone and cyclization of prenylated polyhydroxychalcone to flavanones (
15) and (
16)
, and flavonol (
17) starting from isoprene (
1). The structures of all three compounds have been characterized by NMR, IR and mass spectroscopy. |
| doi_str_mv | 10.1016/j.ejmech.2005.09.008 |
| format | Article |
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p-hydroxybenzaldehyde, formation of prenylated polyhydroxychalcone and cyclization of prenylated polyhydroxychalcone to flavanones (
15) and (
16)
, and flavonol (
17) starting from isoprene (
1). The structures of all three compounds have been characterized by NMR, IR and mass spectroscopy.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2005.09.008</identifier><identifier>PMID: 16330130</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Oxford: Elsevier Masson SAS</publisher><subject>Abyssinone II ; Anticarcinogenic Agents - chemical synthesis ; Anticarcinogenic Agents - pharmacology ; Aromatase - metabolism ; Biological and medical sciences ; Carcinogenesis, carcinogens and anticarcinogens ; Chalcone - analogs & derivatives ; Chemical agents ; Chemistry ; Chemoprevention ; Exact sciences and technology ; Flavanones - chemical synthesis ; Flavanones - pharmacology ; Flavonoids ; Flavonoids - chemical synthesis ; Flavonoids - pharmacology ; Flavonols - chemical synthesis ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Medical sciences ; Organic chemistry ; Plants, Medicinal - chemistry ; Polyhydroxychalcone ; Prenylated chalcone ; Prenylation ; Preparations and properties ; Protein Prenylation ; Spectrum Analysis ; Tumors</subject><ispartof>European journal of medicinal chemistry, 2006-02, Vol.41 (2), p.263-267</ispartof><rights>2005 Elsevier SAS</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-bd3cad62f7118594ab3c62d20cfaa4fa6a49d97e5e7c14578d4048e5dd51b9103</citedby><cites>FETCH-LOGICAL-c390t-bd3cad62f7118594ab3c62d20cfaa4fa6a49d97e5e7c14578d4048e5dd51b9103</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0223523405002709$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27903,27904,65309</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17634180$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16330130$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Moriarty, Robert M.</creatorcontrib><creatorcontrib>Grubjesic, Simonida</creatorcontrib><creatorcontrib>Surve, Bhushan C.</creatorcontrib><creatorcontrib>Chandersekera, Susantha N.</creatorcontrib><creatorcontrib>Prakash, Om</creatorcontrib><creatorcontrib>Naithani, Rajesh</creatorcontrib><title>Synthesis of Abyssinone II and related compounds as potential chemopreventive agents</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>A facile and efficient approach to the synthesis of prenylated flavonoids as potential chemopreventive agents has been described. This features the synthesis of prenyl halide, prenylation of
p-hydroxybenzaldehyde, formation of prenylated polyhydroxychalcone and cyclization of prenylated polyhydroxychalcone to flavanones (
15) and (
16)
, and flavonol (
17) starting from isoprene (
1). The structures of all three compounds have been characterized by NMR, IR and mass spectroscopy.</description><subject>Abyssinone II</subject><subject>Anticarcinogenic Agents - chemical synthesis</subject><subject>Anticarcinogenic Agents - pharmacology</subject><subject>Aromatase - metabolism</subject><subject>Biological and medical sciences</subject><subject>Carcinogenesis, carcinogens and anticarcinogens</subject><subject>Chalcone - analogs & derivatives</subject><subject>Chemical agents</subject><subject>Chemistry</subject><subject>Chemoprevention</subject><subject>Exact sciences and technology</subject><subject>Flavanones - chemical synthesis</subject><subject>Flavanones - pharmacology</subject><subject>Flavonoids</subject><subject>Flavonoids - chemical synthesis</subject><subject>Flavonoids - pharmacology</subject><subject>Flavonols - chemical synthesis</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Medical sciences</subject><subject>Organic chemistry</subject><subject>Plants, Medicinal - chemistry</subject><subject>Polyhydroxychalcone</subject><subject>Prenylated chalcone</subject><subject>Prenylation</subject><subject>Preparations and properties</subject><subject>Protein Prenylation</subject><subject>Spectrum Analysis</subject><subject>Tumors</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kM-K1EAQhxtR3NnVNxDJRW-J1X-TXIRlUXdgwYOKx6bTXXF6SLpjd2Zg3maeZZ7MDDOwN09VBd_vR_ER8o5CRYGqT9sKtyPaTcUAZAVtBdC8ICtaq6bkTIqXZAWM8VIyLm7Ibc5bWEAF8JrcUMU5UA4r8vvHIcwbzD4XsT8d77tDzj7EgMV6XZjgTseEg5nRFTaOU9wFlwuTT8cpzhhmb4bCbnCMU8L9-d5jYf4sS35DXvVmyPj2Ou_Ir69ffj48lk_fv60f7p9Ky1uYy85xa5xifU1pI1thOm4Vcwxsb4zojTKidW2NEmtLhawbJ0A0KJ2TtGsp8Dvy8dI7pfh3h3nWo88Wh8EEjLusVV0rxiRdQHEBbYo5J-z1lPxo0kFT0GeheqsvQvVZqIZWL0KX2Ptr_64b0T2HrgYX4MMVMNmaoU8mWJ-fuVpxQZsz9_nC4WJj7zHpbD0Gi84ntLN20f__k3_RjZlE</recordid><startdate>20060201</startdate><enddate>20060201</enddate><creator>Moriarty, Robert M.</creator><creator>Grubjesic, Simonida</creator><creator>Surve, Bhushan C.</creator><creator>Chandersekera, Susantha N.</creator><creator>Prakash, Om</creator><creator>Naithani, Rajesh</creator><general>Elsevier Masson SAS</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>20060201</creationdate><title>Synthesis of Abyssinone II and related compounds as potential chemopreventive agents</title><author>Moriarty, Robert M. ; Grubjesic, Simonida ; Surve, Bhushan C. ; Chandersekera, Susantha N. ; Prakash, Om ; Naithani, Rajesh</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-bd3cad62f7118594ab3c62d20cfaa4fa6a49d97e5e7c14578d4048e5dd51b9103</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Abyssinone II</topic><topic>Anticarcinogenic Agents - chemical synthesis</topic><topic>Anticarcinogenic Agents - pharmacology</topic><topic>Aromatase - metabolism</topic><topic>Biological and medical sciences</topic><topic>Carcinogenesis, carcinogens and anticarcinogens</topic><topic>Chalcone - analogs & derivatives</topic><topic>Chemical agents</topic><topic>Chemistry</topic><topic>Chemoprevention</topic><topic>Exact sciences and technology</topic><topic>Flavanones - chemical synthesis</topic><topic>Flavanones - pharmacology</topic><topic>Flavonoids</topic><topic>Flavonoids - chemical synthesis</topic><topic>Flavonoids - pharmacology</topic><topic>Flavonols - chemical synthesis</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Medical sciences</topic><topic>Organic chemistry</topic><topic>Plants, Medicinal - chemistry</topic><topic>Polyhydroxychalcone</topic><topic>Prenylated chalcone</topic><topic>Prenylation</topic><topic>Preparations and properties</topic><topic>Protein Prenylation</topic><topic>Spectrum Analysis</topic><topic>Tumors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Moriarty, Robert M.</creatorcontrib><creatorcontrib>Grubjesic, Simonida</creatorcontrib><creatorcontrib>Surve, Bhushan C.</creatorcontrib><creatorcontrib>Chandersekera, Susantha N.</creatorcontrib><creatorcontrib>Prakash, Om</creatorcontrib><creatorcontrib>Naithani, Rajesh</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>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Moriarty, Robert M.</au><au>Grubjesic, Simonida</au><au>Surve, Bhushan C.</au><au>Chandersekera, Susantha N.</au><au>Prakash, Om</au><au>Naithani, Rajesh</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Abyssinone II and related compounds as potential chemopreventive agents</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2006-02-01</date><risdate>2006</risdate><volume>41</volume><issue>2</issue><spage>263</spage><epage>267</epage><pages>263-267</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>A facile and efficient approach to the synthesis of prenylated flavonoids as potential chemopreventive agents has been described. This features the synthesis of prenyl halide, prenylation of
p-hydroxybenzaldehyde, formation of prenylated polyhydroxychalcone and cyclization of prenylated polyhydroxychalcone to flavanones (
15) and (
16)
, and flavonol (
17) starting from isoprene (
1). The structures of all three compounds have been characterized by NMR, IR and mass spectroscopy.</abstract><cop>Oxford</cop><pub>Elsevier Masson SAS</pub><pmid>16330130</pmid><doi>10.1016/j.ejmech.2005.09.008</doi><tpages>5</tpages></addata></record> |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Abyssinone II Anticarcinogenic Agents - chemical synthesis Anticarcinogenic Agents - pharmacology Aromatase - metabolism Biological and medical sciences Carcinogenesis, carcinogens and anticarcinogens Chalcone - analogs & derivatives Chemical agents Chemistry Chemoprevention Exact sciences and technology Flavanones - chemical synthesis Flavanones - pharmacology Flavonoids Flavonoids - chemical synthesis Flavonoids - pharmacology Flavonols - chemical synthesis Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Medical sciences Organic chemistry Plants, Medicinal - chemistry Polyhydroxychalcone Prenylated chalcone Prenylation Preparations and properties Protein Prenylation Spectrum Analysis Tumors |
| title | Synthesis of Abyssinone II and related compounds as potential chemopreventive agents |
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