An Additional Spirocyclization for Duocarmycin SA
A unique alternative to the p-spirocyclization for activation of compounds containing the duocarmycin SA alkylation subunit was established involving indole NH deprotonation and subsequent cyclopropane formation. The structural characterization of an alternative spirocyclization product and the esta...
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| Veröffentlicht in: | Journal of the American Chemical Society 2008-12, Vol.130 (49), p.16521-16523 |
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| container_end_page | 16523 |
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| container_issue | 49 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 130 |
| creator | MacMillan, Karen S Boger, Dale L |
| description | A unique alternative to the p-spirocyclization for activation of compounds containing the duocarmycin SA alkylation subunit was established involving indole NH deprotonation and subsequent cyclopropane formation. The structural characterization of an alternative spirocyclization product and the establishment of its relative reactivity, intrinsic reaction regioselectivity, biological activity, and DNA alkylation properties (selectivity, rate, and efficiency) including the isolation, characterization, and quantitation of its adenine N3 adduct are disclosed. |
| doi_str_mv | 10.1021/ja806593w |
| format | Article |
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The structural characterization of an alternative spirocyclization product and the establishment of its relative reactivity, intrinsic reaction regioselectivity, biological activity, and DNA alkylation properties (selectivity, rate, and efficiency) including the isolation, characterization, and quantitation of its adenine N3 adduct are disclosed.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja806593w</identifier><identifier>PMID: 19554689</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkylation ; Antineoplastic Agents - chemistry ; Cyclization ; Hydrogen-Ion Concentration ; Indoles - chemistry ; Kinetics ; Pyrroles - chemistry</subject><ispartof>Journal of the American Chemical Society, 2008-12, Vol.130 (49), p.16521-16523</ispartof><rights>Copyright © 2008 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a441t-b4b2edee2b3080465dde55ed08a254bc23aec2c599014f59acd768035b17ec643</citedby><cites>FETCH-LOGICAL-a441t-b4b2edee2b3080465dde55ed08a254bc23aec2c599014f59acd768035b17ec643</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/ja806593w$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja806593w$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19554689$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>MacMillan, Karen S</creatorcontrib><creatorcontrib>Boger, Dale L</creatorcontrib><title>An Additional Spirocyclization for Duocarmycin SA</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>A unique alternative to the p-spirocyclization for activation of compounds containing the duocarmycin SA alkylation subunit was established involving indole NH deprotonation and subsequent cyclopropane formation. The structural characterization of an alternative spirocyclization product and the establishment of its relative reactivity, intrinsic reaction regioselectivity, biological activity, and DNA alkylation properties (selectivity, rate, and efficiency) including the isolation, characterization, and quantitation of its adenine N3 adduct are disclosed.</description><subject>Alkylation</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Cyclization</subject><subject>Hydrogen-Ion Concentration</subject><subject>Indoles - chemistry</subject><subject>Kinetics</subject><subject>Pyrroles - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkFFLwzAUhYMoOqcP_gHpiw8-VJM0SdsXoUyd4sBJ515DmqSa2TUj6dT56-3omAo-Xe493z0HDgAnCF4giNHlTCSQ0TT62AE9RDEMKcJsF_QghDiMExYdgEPvZ-1KcIL2wQFKKSUsSXsAZXWQKWUaY2tRBfnCOCtXsjJfYn0KSuuC66WVws1X0tRBnh2BvVJUXh9vZh88395MBnfh6HF4P8hGoSAENWFBCqyV1riIYAIJo0ppSrWCicCUFBJHQkssaZpCREqaCqlilsCIFijWkpGoD64638WymGsldd04UfGFM3PhVtwKw_8qtXnlL_ad4yRFlMatwXlnIJ313uly-4sgX_fGt7217OnvsB9yU1QLhB1gfKM_t7pwb5zFUUz5ZJzzcT58Gj3AKZ-2_FnHC-n5zC5d267_J_gbY-GEpA</recordid><startdate>20081210</startdate><enddate>20081210</enddate><creator>MacMillan, Karen S</creator><creator>Boger, Dale L</creator><general>American Chemical Society</general><scope>BSCLL</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>5PM</scope></search><sort><creationdate>20081210</creationdate><title>An Additional Spirocyclization for Duocarmycin SA</title><author>MacMillan, Karen S ; Boger, Dale L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a441t-b4b2edee2b3080465dde55ed08a254bc23aec2c599014f59acd768035b17ec643</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Alkylation</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Cyclization</topic><topic>Hydrogen-Ion Concentration</topic><topic>Indoles - chemistry</topic><topic>Kinetics</topic><topic>Pyrroles - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>MacMillan, Karen S</creatorcontrib><creatorcontrib>Boger, Dale L</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>MacMillan, Karen S</au><au>Boger, Dale L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Additional Spirocyclization for Duocarmycin SA</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2008-12-10</date><risdate>2008</risdate><volume>130</volume><issue>49</issue><spage>16521</spage><epage>16523</epage><pages>16521-16523</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>A unique alternative to the p-spirocyclization for activation of compounds containing the duocarmycin SA alkylation subunit was established involving indole NH deprotonation and subsequent cyclopropane formation. The structural characterization of an alternative spirocyclization product and the establishment of its relative reactivity, intrinsic reaction regioselectivity, biological activity, and DNA alkylation properties (selectivity, rate, and efficiency) including the isolation, characterization, and quantitation of its adenine N3 adduct are disclosed.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>19554689</pmid><doi>10.1021/ja806593w</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Journal of the American Chemical Society, 2008-12, Vol.130 (49), p.16521-16523 |
| issn | 0002-7863 1520-5126 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_2891557 |
| source | ACS Publications; MEDLINE |
| subjects | Alkylation Antineoplastic Agents - chemistry Cyclization Hydrogen-Ion Concentration Indoles - chemistry Kinetics Pyrroles - chemistry |
| title | An Additional Spirocyclization for Duocarmycin SA |
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