Palladium catalyzed synthesis of benzannulated steroid spiroketals
Nine cytotoxic [5/7] and [6/6] benzannulated steroid spiroketals were synthesized by palladium catalyzed spiroketalization of 5α and 5β-alkynediols derived from testosterone, diosgenin and cholesterol. The regioselectivity of the spiroketalization reaction is decisively influenced by the α or β-orie...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2020-01, Vol.18 (4), p.725-737 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Mayorquín-Torres, Martha C González-Orozco, Juan Carlos Flores-Álamo, Marcos Camacho-Arroyo, Ignacio Iglesias-Arteaga, Martín A |
| description | Nine cytotoxic [5/7] and [6/6] benzannulated steroid spiroketals were synthesized by palladium catalyzed spiroketalization of 5α and 5β-alkynediols derived from testosterone, diosgenin and cholesterol. The regioselectivity of the spiroketalization reaction is decisively influenced by the α or β-orientation of the hydroxyl group at C-5. NMR and single crystal X-ray diffraction corroborated the structure of the obtained compounds. Compounds bearing a cholestane skeleton exhibited higher cytotoxicity against U251 and T47D cells, and the BrdU incorporation assay suggests that the synthesized spiroketals inhibit cell proliferation.
Nine cytotoxic [5/7] and [6/6] benzannulated steroid spiroketals were synthesized by palladium catalyzed spiroketalization of 5α and 5β-alkynediols derived from testosterone, diosgenin and cholesterol. |
| doi_str_mv | 10.1039/c9ob02255d |
| format | Article |
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Nine cytotoxic [5/7] and [6/6] benzannulated steroid spiroketals were synthesized by palladium catalyzed spiroketalization of 5α and 5β-alkynediols derived from testosterone, diosgenin and cholesterol.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c9ob02255d</identifier><identifier>PMID: 31912858</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkynes ; Cell proliferation ; Chemical synthesis ; Cholesterol ; Crystal structure ; Crystallography ; Crystals ; Cytotoxicity ; Hydroxyl groups ; NMR ; Nuclear magnetic resonance ; Palladium ; Regioselectivity ; Single crystals ; Steroids ; Testosterone ; Toxicity ; X-ray diffraction</subject><ispartof>Organic & biomolecular chemistry, 2020-01, Vol.18 (4), p.725-737</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c363t-6a741743ee74689fa247516defa35993b229daf58ec253ff78a35b4dfff69fb23</citedby><cites>FETCH-LOGICAL-c363t-6a741743ee74689fa247516defa35993b229daf58ec253ff78a35b4dfff69fb23</cites><orcidid>0000-0002-2996-7616 ; 0000-0002-0703-4049 ; 0000-0003-2978-1253 ; 0000-0003-4764-7664 ; 0000-0002-2338-9755</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31912858$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mayorquín-Torres, Martha C</creatorcontrib><creatorcontrib>González-Orozco, Juan Carlos</creatorcontrib><creatorcontrib>Flores-Álamo, Marcos</creatorcontrib><creatorcontrib>Camacho-Arroyo, Ignacio</creatorcontrib><creatorcontrib>Iglesias-Arteaga, Martín A</creatorcontrib><title>Palladium catalyzed synthesis of benzannulated steroid spiroketals</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Nine cytotoxic [5/7] and [6/6] benzannulated steroid spiroketals were synthesized by palladium catalyzed spiroketalization of 5α and 5β-alkynediols derived from testosterone, diosgenin and cholesterol. The regioselectivity of the spiroketalization reaction is decisively influenced by the α or β-orientation of the hydroxyl group at C-5. NMR and single crystal X-ray diffraction corroborated the structure of the obtained compounds. Compounds bearing a cholestane skeleton exhibited higher cytotoxicity against U251 and T47D cells, and the BrdU incorporation assay suggests that the synthesized spiroketals inhibit cell proliferation.
Nine cytotoxic [5/7] and [6/6] benzannulated steroid spiroketals were synthesized by palladium catalyzed spiroketalization of 5α and 5β-alkynediols derived from testosterone, diosgenin and cholesterol.</description><subject>Alkynes</subject><subject>Cell proliferation</subject><subject>Chemical synthesis</subject><subject>Cholesterol</subject><subject>Crystal structure</subject><subject>Crystallography</subject><subject>Crystals</subject><subject>Cytotoxicity</subject><subject>Hydroxyl groups</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Palladium</subject><subject>Regioselectivity</subject><subject>Single crystals</subject><subject>Steroids</subject><subject>Testosterone</subject><subject>Toxicity</subject><subject>X-ray diffraction</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp90TtPwzAQAGALgWgpLOygIBaEFPAzjse2PKVKZYA5cmJbpCRxsJOh_fW4tBSJgcVn-T6fzmcAThG8QZCI20LYHGLMmNoDQ0Q5jyEjYn-3x3AAjrxfQIgET-ghGBAkEE5ZOgSTF1lVUpV9HRWyk9VypVXkl033rn3pI2uiXDcr2TR9Jbt1qtPOliG2pbMfOtzwx-DAhKBPtnEE3h7uX6dP8Wz--Dwdz-KCJKSLE8kp4pRozWmSCiMx5QwlShtJmBAkx1goaViqC8yIMTwN5zlVxphEmByTEbja1G2d_ey177K69IUO7Tfa9j7DhFAe3ghhoJd_6ML2rgndBUU5oWERQV1vVOGs906brHVlLd0yQzBbTzabivnke7J3AZ9vS_Z5rdWO_owygIsNcL7YZX-_JmuVCebsP0O-AFjBiKc</recordid><startdate>20200128</startdate><enddate>20200128</enddate><creator>Mayorquín-Torres, Martha C</creator><creator>González-Orozco, Juan Carlos</creator><creator>Flores-Álamo, Marcos</creator><creator>Camacho-Arroyo, Ignacio</creator><creator>Iglesias-Arteaga, Martín A</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-2996-7616</orcidid><orcidid>https://orcid.org/0000-0002-0703-4049</orcidid><orcidid>https://orcid.org/0000-0003-2978-1253</orcidid><orcidid>https://orcid.org/0000-0003-4764-7664</orcidid><orcidid>https://orcid.org/0000-0002-2338-9755</orcidid></search><sort><creationdate>20200128</creationdate><title>Palladium catalyzed synthesis of benzannulated steroid spiroketals</title><author>Mayorquín-Torres, Martha C ; González-Orozco, Juan Carlos ; Flores-Álamo, Marcos ; Camacho-Arroyo, Ignacio ; Iglesias-Arteaga, Martín A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c363t-6a741743ee74689fa247516defa35993b229daf58ec253ff78a35b4dfff69fb23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkynes</topic><topic>Cell proliferation</topic><topic>Chemical synthesis</topic><topic>Cholesterol</topic><topic>Crystal structure</topic><topic>Crystallography</topic><topic>Crystals</topic><topic>Cytotoxicity</topic><topic>Hydroxyl groups</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Palladium</topic><topic>Regioselectivity</topic><topic>Single crystals</topic><topic>Steroids</topic><topic>Testosterone</topic><topic>Toxicity</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mayorquín-Torres, Martha C</creatorcontrib><creatorcontrib>González-Orozco, Juan Carlos</creatorcontrib><creatorcontrib>Flores-Álamo, Marcos</creatorcontrib><creatorcontrib>Camacho-Arroyo, Ignacio</creatorcontrib><creatorcontrib>Iglesias-Arteaga, Martín A</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mayorquín-Torres, Martha C</au><au>González-Orozco, Juan Carlos</au><au>Flores-Álamo, Marcos</au><au>Camacho-Arroyo, Ignacio</au><au>Iglesias-Arteaga, Martín A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium catalyzed synthesis of benzannulated steroid spiroketals</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2020-01-28</date><risdate>2020</risdate><volume>18</volume><issue>4</issue><spage>725</spage><epage>737</epage><pages>725-737</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Nine cytotoxic [5/7] and [6/6] benzannulated steroid spiroketals were synthesized by palladium catalyzed spiroketalization of 5α and 5β-alkynediols derived from testosterone, diosgenin and cholesterol. The regioselectivity of the spiroketalization reaction is decisively influenced by the α or β-orientation of the hydroxyl group at C-5. NMR and single crystal X-ray diffraction corroborated the structure of the obtained compounds. Compounds bearing a cholestane skeleton exhibited higher cytotoxicity against U251 and T47D cells, and the BrdU incorporation assay suggests that the synthesized spiroketals inhibit cell proliferation.
Nine cytotoxic [5/7] and [6/6] benzannulated steroid spiroketals were synthesized by palladium catalyzed spiroketalization of 5α and 5β-alkynediols derived from testosterone, diosgenin and cholesterol.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>31912858</pmid><doi>10.1039/c9ob02255d</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0002-2996-7616</orcidid><orcidid>https://orcid.org/0000-0002-0703-4049</orcidid><orcidid>https://orcid.org/0000-0003-2978-1253</orcidid><orcidid>https://orcid.org/0000-0003-4764-7664</orcidid><orcidid>https://orcid.org/0000-0002-2338-9755</orcidid></addata></record> |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alkynes Cell proliferation Chemical synthesis Cholesterol Crystal structure Crystallography Crystals Cytotoxicity Hydroxyl groups NMR Nuclear magnetic resonance Palladium Regioselectivity Single crystals Steroids Testosterone Toxicity X-ray diffraction |
| title | Palladium catalyzed synthesis of benzannulated steroid spiroketals |
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