Development of carbamate-tethered coumarins as phototriggers for caged nicotinamide
The syntheses of 7-diethylaminocoumarin- or modified DEACM-nicotinamide and 6-bromo-7-methoxycoumarin- or BMCM-nicotinamide have been accomplished by reaction of nicotinoyl isocyanate with the corresponding coumarin allylic alcohol derivatives. The resulting compounds contain an N-acyl O-alkyl carba...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2013-12, Vol.23 (23), p.6321-6324 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Bourbon, Pauline Peng, Qian Ferraudi, Guillermo Stauffacher, Cynthia Wiest, Olaf Helquist, Paul |
| description | The syntheses of 7-diethylaminocoumarin- or modified DEACM-nicotinamide and 6-bromo-7-methoxycoumarin- or BMCM-nicotinamide have been accomplished by reaction of nicotinoyl isocyanate with the corresponding coumarin allylic alcohol derivatives. The resulting compounds contain an N-acyl O-alkyl carbamate as a new type of linkage for the caging of nicotinamide with a coumarin phototrigger, which undergoes cleavage upon photolysis. Our design of specific caged-nicotinamides was based upon NBO and TD-FT calculations to predict absorption wavelengths and photocleavage potential. This work provides a potentially general method for the caging of amides with coumarin photolabile protecting groups. |
| doi_str_mv | 10.1016/j.bmcl.2013.09.067 |
| format | Article |
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The resulting compounds contain an N-acyl O-alkyl carbamate as a new type of linkage for the caging of nicotinamide with a coumarin phototrigger, which undergoes cleavage upon photolysis. Our design of specific caged-nicotinamides was based upon NBO and TD-FT calculations to predict absorption wavelengths and photocleavage potential. This work provides a potentially general method for the caging of amides with coumarin photolabile protecting groups.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2013.09.067</identifier><identifier>PMID: 24125882</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>absorption ; alcohols ; Caged compound ; Carbamates - chemical synthesis ; Carbamates - chemistry ; Coumarin ; Coumarins - chemical synthesis ; Coumarins - chemistry ; Niacinamide - chemical synthesis ; Niacinamide - chemistry ; Nicotinamide ; Photochemical Processes ; Photocleavage ; photolysis ; wavelengths</subject><ispartof>Bioorganic & medicinal chemistry letters, 2013-12, Vol.23 (23), p.6321-6324</ispartof><rights>2013 Elsevier Ltd</rights><rights>Copyright © 2013 Elsevier Ltd. 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The resulting compounds contain an N-acyl O-alkyl carbamate as a new type of linkage for the caging of nicotinamide with a coumarin phototrigger, which undergoes cleavage upon photolysis. Our design of specific caged-nicotinamides was based upon NBO and TD-FT calculations to predict absorption wavelengths and photocleavage potential. This work provides a potentially general method for the caging of amides with coumarin photolabile protecting groups.</description><subject>absorption</subject><subject>alcohols</subject><subject>Caged compound</subject><subject>Carbamates - chemical synthesis</subject><subject>Carbamates - chemistry</subject><subject>Coumarin</subject><subject>Coumarins - chemical synthesis</subject><subject>Coumarins - chemistry</subject><subject>Niacinamide - chemical synthesis</subject><subject>Niacinamide - chemistry</subject><subject>Nicotinamide</subject><subject>Photochemical Processes</subject><subject>Photocleavage</subject><subject>photolysis</subject><subject>wavelengths</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEtv1DAUhS0EokPhD7CALNkkXMePxBIbVFpAqtRFW4md5cfN1KMkHmxPJf49Hk1hCasrXX3n6Ogj5C2FjgKVH3edXdzc9UBZB6oDOTwjG8olbxkH8ZxsQEloR8V_nJFXOe8AKAfOX5KzntNejGO_Ibdf8BHnuF9wLU2cGmeSNYsp2BYsD5jQNy4eFpPCmhuTm_1DLLGksN1iys0UU01sK7QGF0tYzRI8viYvJjNnfPN0z8n91eXdxbf2-ubr94vP163jlJVWUK8GZhn1g-FOci_4MFknZH0pNjjJqBBqnBQfwQlvQUzWS-cHO4GVTLFz8uHUu0_x5wFz0UvIDufZrBgPWVMBMAg59PT_KOdjD2ocjq39CXUp5pxw0vsUqoBfmoI-etc7ffSuj941KF2919C7p_6DXdD_jfwRXYH3J2AyUZttClnf39aGOpGyXjJRiU8nAquyx4BJZxdwdehDQle0j-FfC34DLomdRQ</recordid><startdate>20131201</startdate><enddate>20131201</enddate><creator>Bourbon, Pauline</creator><creator>Peng, Qian</creator><creator>Ferraudi, Guillermo</creator><creator>Stauffacher, Cynthia</creator><creator>Wiest, Olaf</creator><creator>Helquist, Paul</creator><general>Elsevier Ltd</general><scope>FBQ</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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20131201</creationdate><title>Development of carbamate-tethered coumarins as phototriggers for caged nicotinamide</title><author>Bourbon, Pauline ; Peng, Qian ; Ferraudi, Guillermo ; Stauffacher, Cynthia ; Wiest, Olaf ; Helquist, Paul</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c413t-51d973b31d7a4c64d547fbc56b31937c6315598f9480c5db05fbd6cd7bf0b6393</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>absorption</topic><topic>alcohols</topic><topic>Caged compound</topic><topic>Carbamates - chemical synthesis</topic><topic>Carbamates - chemistry</topic><topic>Coumarin</topic><topic>Coumarins - chemical synthesis</topic><topic>Coumarins - chemistry</topic><topic>Niacinamide - chemical synthesis</topic><topic>Niacinamide - chemistry</topic><topic>Nicotinamide</topic><topic>Photochemical Processes</topic><topic>Photocleavage</topic><topic>photolysis</topic><topic>wavelengths</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bourbon, Pauline</creatorcontrib><creatorcontrib>Peng, Qian</creatorcontrib><creatorcontrib>Ferraudi, Guillermo</creatorcontrib><creatorcontrib>Stauffacher, Cynthia</creatorcontrib><creatorcontrib>Wiest, Olaf</creatorcontrib><creatorcontrib>Helquist, Paul</creatorcontrib><collection>AGRIS</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><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bourbon, Pauline</au><au>Peng, Qian</au><au>Ferraudi, Guillermo</au><au>Stauffacher, Cynthia</au><au>Wiest, Olaf</au><au>Helquist, Paul</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Development of carbamate-tethered coumarins as phototriggers for caged nicotinamide</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2013-12-01</date><risdate>2013</risdate><volume>23</volume><issue>23</issue><spage>6321</spage><epage>6324</epage><pages>6321-6324</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>The syntheses of 7-diethylaminocoumarin- or modified DEACM-nicotinamide and 6-bromo-7-methoxycoumarin- or BMCM-nicotinamide have been accomplished by reaction of nicotinoyl isocyanate with the corresponding coumarin allylic alcohol derivatives. 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| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2013-12, Vol.23 (23), p.6321-6324 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | absorption alcohols Caged compound Carbamates - chemical synthesis Carbamates - chemistry Coumarin Coumarins - chemical synthesis Coumarins - chemistry Niacinamide - chemical synthesis Niacinamide - chemistry Nicotinamide Photochemical Processes Photocleavage photolysis wavelengths |
| title | Development of carbamate-tethered coumarins as phototriggers for caged nicotinamide |
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