Synthesis and biological studies of “Polycerasoidol” and “trans-δ-Tocotrienolic acid” derivatives as PPARα and/or PPARγ agonists
[Display omitted] 2-Prenylated benzopyrans represent a class of natural and synthetic compounds showing a wide range of significant activities. Polycerasoidol is a natural prenylated benzopyran isolated from the stem bark of Polyalthia cerasoides (Annonaceae) that exhibits dual PPARα/γ agonism and a...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2022-01, Vol.53, p.116532-116532, Article 116532 |
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| creator | Vila, Laura Cabedo, Nuria Villarroel-Vicente, Carlos García, Ainhoa Bernabeu, Álvaro Hennuyer, Nathalie Staels, Bart Franck, Xavier Figadère, Bruno Sanz, María-Jesús Cortes, Diego |
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2-Prenylated benzopyrans represent a class of natural and synthetic compounds showing a wide range of significant activities. Polycerasoidol is a natural prenylated benzopyran isolated from the stem bark of Polyalthia cerasoides (Annonaceae) that exhibits dual PPARα/γ agonism and an anti-inflammatory effect by inhibiting mononuclear leukocyte adhesion to the dysfunctional endothelium. Herein, we report the synthesis of three new series of prenylated benzopyrans containing one (series 1), two (series 2, “polycerasoidol” analogs) and three (series 3, “trans-δ-tocotrienolic acid” analogs) isoprenoid units in the hydrocarbon side chain at the 2-position of the chroman-6-ol (6-hydroxy-dihydrobenzopyran) scaffold. Isoprenoid moieties were introduced through a Grignard reaction sequence, followed by Johnson-Claisen rearrangement and subsequent Wittig olefination. hPPAR transactivation activity and the structure activity relationships (SAR) of eleven novel synthesized 2-prenylated benzopyrans were explored. PPAR transactivation activity demonstrated that the seven-carbon side chain analogs (series 1) displayed selectivity for hPPARα, while the nine-carbon side chain analogs (polycerasoidol analogs, series 2) did so for hPPARγ. The side chain elongation to 11 or 13 carbons (series 3) resulted in weak dual PPARα/γ activation. Therefore, 2-prenylated benzopyrans of seven- and nine-carbon side chain (polycerasoidol analogs) are good lead compounds for developing useful candidates to prevent cardiovascular diseases associated with metabolic disorders. |
| doi_str_mv | 10.1016/j.bmc.2021.116532 |
| format | Article |
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2-Prenylated benzopyrans represent a class of natural and synthetic compounds showing a wide range of significant activities. Polycerasoidol is a natural prenylated benzopyran isolated from the stem bark of Polyalthia cerasoides (Annonaceae) that exhibits dual PPARα/γ agonism and an anti-inflammatory effect by inhibiting mononuclear leukocyte adhesion to the dysfunctional endothelium. Herein, we report the synthesis of three new series of prenylated benzopyrans containing one (series 1), two (series 2, “polycerasoidol” analogs) and three (series 3, “trans-δ-tocotrienolic acid” analogs) isoprenoid units in the hydrocarbon side chain at the 2-position of the chroman-6-ol (6-hydroxy-dihydrobenzopyran) scaffold. Isoprenoid moieties were introduced through a Grignard reaction sequence, followed by Johnson-Claisen rearrangement and subsequent Wittig olefination. hPPAR transactivation activity and the structure activity relationships (SAR) of eleven novel synthesized 2-prenylated benzopyrans were explored. PPAR transactivation activity demonstrated that the seven-carbon side chain analogs (series 1) displayed selectivity for hPPARα, while the nine-carbon side chain analogs (polycerasoidol analogs, series 2) did so for hPPARγ. The side chain elongation to 11 or 13 carbons (series 3) resulted in weak dual PPARα/γ activation. Therefore, 2-prenylated benzopyrans of seven- and nine-carbon side chain (polycerasoidol analogs) are good lead compounds for developing useful candidates to prevent cardiovascular diseases associated with metabolic disorders.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2021.116532</identifier><identifier>PMID: 34863066</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>2-Prenylated benzopyrans ; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis ; Anti-Inflammatory Agents, Non-Steroidal - chemistry ; Anti-Inflammatory Agents, Non-Steroidal - pharmacology ; Benzopyrans - chemical synthesis ; Benzopyrans - chemistry ; Benzopyrans - pharmacology ; Chemical Sciences ; Dose-Response Relationship, Drug ; Grignard/Johnson-Claisen rearrangement ; hPPAR activity ; Humans ; Medicinal Chemistry ; Molecular Structure ; Organic chemistry ; Polycerasoidol analogs ; PPAR alpha - agonists ; PPAR gamma - agonists ; Structure-Activity Relationship ; Tocotrienol analogs ; Vitamin E - analogs & derivatives ; Vitamin E - chemical synthesis ; Vitamin E - chemistry ; Vitamin E - pharmacology ; Wittig olefination</subject><ispartof>Bioorganic & medicinal chemistry, 2022-01, Vol.53, p.116532-116532, Article 116532</ispartof><rights>2021 Elsevier Ltd</rights><rights>Copyright © 2021 Elsevier Ltd. All rights reserved.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c430t-46fe8316e347b295e513ea32a4d63aa903d5e55d918fdfeef20dfb9141fd01b43</citedby><cites>FETCH-LOGICAL-c430t-46fe8316e347b295e513ea32a4d63aa903d5e55d918fdfeef20dfb9141fd01b43</cites><orcidid>0000-0001-6729-8057 ; 0000-0002-8885-294X ; 0000-0003-4226-8489 ; 0000-0003-0303-7258 ; 0000-0002-5615-7504 ; 0000-0002-3784-1503</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2021.116532$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,4024,27923,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34863066$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://normandie-univ.hal.science/hal-03463394$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Vila, Laura</creatorcontrib><creatorcontrib>Cabedo, Nuria</creatorcontrib><creatorcontrib>Villarroel-Vicente, Carlos</creatorcontrib><creatorcontrib>García, Ainhoa</creatorcontrib><creatorcontrib>Bernabeu, Álvaro</creatorcontrib><creatorcontrib>Hennuyer, Nathalie</creatorcontrib><creatorcontrib>Staels, Bart</creatorcontrib><creatorcontrib>Franck, Xavier</creatorcontrib><creatorcontrib>Figadère, Bruno</creatorcontrib><creatorcontrib>Sanz, María-Jesús</creatorcontrib><creatorcontrib>Cortes, Diego</creatorcontrib><title>Synthesis and biological studies of “Polycerasoidol” and “trans-δ-Tocotrienolic acid” derivatives as PPARα and/or PPARγ agonists</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>[Display omitted]
2-Prenylated benzopyrans represent a class of natural and synthetic compounds showing a wide range of significant activities. Polycerasoidol is a natural prenylated benzopyran isolated from the stem bark of Polyalthia cerasoides (Annonaceae) that exhibits dual PPARα/γ agonism and an anti-inflammatory effect by inhibiting mononuclear leukocyte adhesion to the dysfunctional endothelium. Herein, we report the synthesis of three new series of prenylated benzopyrans containing one (series 1), two (series 2, “polycerasoidol” analogs) and three (series 3, “trans-δ-tocotrienolic acid” analogs) isoprenoid units in the hydrocarbon side chain at the 2-position of the chroman-6-ol (6-hydroxy-dihydrobenzopyran) scaffold. Isoprenoid moieties were introduced through a Grignard reaction sequence, followed by Johnson-Claisen rearrangement and subsequent Wittig olefination. hPPAR transactivation activity and the structure activity relationships (SAR) of eleven novel synthesized 2-prenylated benzopyrans were explored. PPAR transactivation activity demonstrated that the seven-carbon side chain analogs (series 1) displayed selectivity for hPPARα, while the nine-carbon side chain analogs (polycerasoidol analogs, series 2) did so for hPPARγ. The side chain elongation to 11 or 13 carbons (series 3) resulted in weak dual PPARα/γ activation. Therefore, 2-prenylated benzopyrans of seven- and nine-carbon side chain (polycerasoidol analogs) are good lead compounds for developing useful candidates to prevent cardiovascular diseases associated with metabolic disorders.</description><subject>2-Prenylated benzopyrans</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - chemistry</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - pharmacology</subject><subject>Benzopyrans - chemical synthesis</subject><subject>Benzopyrans - chemistry</subject><subject>Benzopyrans - pharmacology</subject><subject>Chemical Sciences</subject><subject>Dose-Response Relationship, Drug</subject><subject>Grignard/Johnson-Claisen rearrangement</subject><subject>hPPAR activity</subject><subject>Humans</subject><subject>Medicinal Chemistry</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Polycerasoidol analogs</subject><subject>PPAR alpha - agonists</subject><subject>PPAR gamma - agonists</subject><subject>Structure-Activity Relationship</subject><subject>Tocotrienol analogs</subject><subject>Vitamin E - analogs & derivatives</subject><subject>Vitamin E - chemical synthesis</subject><subject>Vitamin E - chemistry</subject><subject>Vitamin E - pharmacology</subject><subject>Wittig olefination</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kUFu1DAUhi0EokPhAGxQlrDI1M92TCxWowoo0kgdlbK2HPul9SgTFzsz0uy65wpwCATn6CF6kjqk7ZKV5fe-9y3-n5DXQOdAQR6t583GzhllMAeQFWdPyAyEFCXnCp6SGVWyLmmt5AF5kdKaUsqEgufkgItacirljPz4uu-HS0w-FaZ3ReNDFy68NV2Rhq3zmIrQFrfXP1eh21uMJgXvQnd7_esfnhdDNH0qb_6W58GGIXrsQ-dtYax3I-Uw-p0Z_C6bTCpWq8XZze_x9ijE6fenMBeh92lIL8mz1nQJX92_h-Tbp4_nxyfl8vTzl-PFsrSC06EUssWag0Qu3jdMVVgBR8OZEU5yYxTlLs8qp6BuXYvYMuraRoGA1lFoBD8k7ybvpen0VfQbE_c6GK9PFks9zigXMkcodpDZtxN7FcP3LaZBb3yy2HWmx7BNmkkqFRMVjFqYUBtDShHbRzdQPfal1zr3pce-9NRXvnlzr982G3SPFw8FZeDDBGAOZOcx6mRzxhadj2gH7YL_j_4OEsOsTQ</recordid><startdate>20220101</startdate><enddate>20220101</enddate><creator>Vila, Laura</creator><creator>Cabedo, Nuria</creator><creator>Villarroel-Vicente, Carlos</creator><creator>García, Ainhoa</creator><creator>Bernabeu, Álvaro</creator><creator>Hennuyer, Nathalie</creator><creator>Staels, Bart</creator><creator>Franck, Xavier</creator><creator>Figadère, Bruno</creator><creator>Sanz, María-Jesús</creator><creator>Cortes, Diego</creator><general>Elsevier Ltd</general><general>Elsevier</general><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><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0001-6729-8057</orcidid><orcidid>https://orcid.org/0000-0002-8885-294X</orcidid><orcidid>https://orcid.org/0000-0003-4226-8489</orcidid><orcidid>https://orcid.org/0000-0003-0303-7258</orcidid><orcidid>https://orcid.org/0000-0002-5615-7504</orcidid><orcidid>https://orcid.org/0000-0002-3784-1503</orcidid></search><sort><creationdate>20220101</creationdate><title>Synthesis and biological studies of “Polycerasoidol” and “trans-δ-Tocotrienolic acid” derivatives as PPARα and/or PPARγ agonists</title><author>Vila, Laura ; Cabedo, Nuria ; Villarroel-Vicente, Carlos ; García, Ainhoa ; Bernabeu, Álvaro ; Hennuyer, Nathalie ; Staels, Bart ; Franck, Xavier ; Figadère, Bruno ; Sanz, María-Jesús ; Cortes, Diego</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c430t-46fe8316e347b295e513ea32a4d63aa903d5e55d918fdfeef20dfb9141fd01b43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>2-Prenylated benzopyrans</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - chemistry</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - pharmacology</topic><topic>Benzopyrans - chemical synthesis</topic><topic>Benzopyrans - chemistry</topic><topic>Benzopyrans - pharmacology</topic><topic>Chemical Sciences</topic><topic>Dose-Response Relationship, Drug</topic><topic>Grignard/Johnson-Claisen rearrangement</topic><topic>hPPAR activity</topic><topic>Humans</topic><topic>Medicinal Chemistry</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Polycerasoidol analogs</topic><topic>PPAR alpha - agonists</topic><topic>PPAR gamma - agonists</topic><topic>Structure-Activity Relationship</topic><topic>Tocotrienol analogs</topic><topic>Vitamin E - analogs & derivatives</topic><topic>Vitamin E - chemical synthesis</topic><topic>Vitamin E - chemistry</topic><topic>Vitamin E - pharmacology</topic><topic>Wittig olefination</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vila, Laura</creatorcontrib><creatorcontrib>Cabedo, Nuria</creatorcontrib><creatorcontrib>Villarroel-Vicente, Carlos</creatorcontrib><creatorcontrib>García, Ainhoa</creatorcontrib><creatorcontrib>Bernabeu, Álvaro</creatorcontrib><creatorcontrib>Hennuyer, Nathalie</creatorcontrib><creatorcontrib>Staels, Bart</creatorcontrib><creatorcontrib>Franck, Xavier</creatorcontrib><creatorcontrib>Figadère, Bruno</creatorcontrib><creatorcontrib>Sanz, María-Jesús</creatorcontrib><creatorcontrib>Cortes, Diego</creatorcontrib><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><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vila, Laura</au><au>Cabedo, Nuria</au><au>Villarroel-Vicente, Carlos</au><au>García, Ainhoa</au><au>Bernabeu, Álvaro</au><au>Hennuyer, Nathalie</au><au>Staels, Bart</au><au>Franck, Xavier</au><au>Figadère, Bruno</au><au>Sanz, María-Jesús</au><au>Cortes, Diego</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and biological studies of “Polycerasoidol” and “trans-δ-Tocotrienolic acid” derivatives as PPARα and/or PPARγ agonists</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2022-01-01</date><risdate>2022</risdate><volume>53</volume><spage>116532</spage><epage>116532</epage><pages>116532-116532</pages><artnum>116532</artnum><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>[Display omitted]
2-Prenylated benzopyrans represent a class of natural and synthetic compounds showing a wide range of significant activities. Polycerasoidol is a natural prenylated benzopyran isolated from the stem bark of Polyalthia cerasoides (Annonaceae) that exhibits dual PPARα/γ agonism and an anti-inflammatory effect by inhibiting mononuclear leukocyte adhesion to the dysfunctional endothelium. Herein, we report the synthesis of three new series of prenylated benzopyrans containing one (series 1), two (series 2, “polycerasoidol” analogs) and three (series 3, “trans-δ-tocotrienolic acid” analogs) isoprenoid units in the hydrocarbon side chain at the 2-position of the chroman-6-ol (6-hydroxy-dihydrobenzopyran) scaffold. Isoprenoid moieties were introduced through a Grignard reaction sequence, followed by Johnson-Claisen rearrangement and subsequent Wittig olefination. hPPAR transactivation activity and the structure activity relationships (SAR) of eleven novel synthesized 2-prenylated benzopyrans were explored. PPAR transactivation activity demonstrated that the seven-carbon side chain analogs (series 1) displayed selectivity for hPPARα, while the nine-carbon side chain analogs (polycerasoidol analogs, series 2) did so for hPPARγ. The side chain elongation to 11 or 13 carbons (series 3) resulted in weak dual PPARα/γ activation. Therefore, 2-prenylated benzopyrans of seven- and nine-carbon side chain (polycerasoidol analogs) are good lead compounds for developing useful candidates to prevent cardiovascular diseases associated with metabolic disorders.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>34863066</pmid><doi>10.1016/j.bmc.2021.116532</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0001-6729-8057</orcidid><orcidid>https://orcid.org/0000-0002-8885-294X</orcidid><orcidid>https://orcid.org/0000-0003-4226-8489</orcidid><orcidid>https://orcid.org/0000-0003-0303-7258</orcidid><orcidid>https://orcid.org/0000-0002-5615-7504</orcidid><orcidid>https://orcid.org/0000-0002-3784-1503</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | 2-Prenylated benzopyrans Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis Anti-Inflammatory Agents, Non-Steroidal - chemistry Anti-Inflammatory Agents, Non-Steroidal - pharmacology Benzopyrans - chemical synthesis Benzopyrans - chemistry Benzopyrans - pharmacology Chemical Sciences Dose-Response Relationship, Drug Grignard/Johnson-Claisen rearrangement hPPAR activity Humans Medicinal Chemistry Molecular Structure Organic chemistry Polycerasoidol analogs PPAR alpha - agonists PPAR gamma - agonists Structure-Activity Relationship Tocotrienol analogs Vitamin E - analogs & derivatives Vitamin E - chemical synthesis Vitamin E - chemistry Vitamin E - pharmacology Wittig olefination |
| title | Synthesis and biological studies of “Polycerasoidol” and “trans-δ-Tocotrienolic acid” derivatives as PPARα and/or PPARγ agonists |
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