Solid-Phase Synthesis of Anagrelide Sulfonyl Analogues
Simple solid-phase synthesis of 3,10-dihydro-2H-benzo[e]imidazo[1,2-b][1,2,4]thiadiazin-2-one 5,5-dioxides is described, with Fmoc-α-amino acids and 2-nitrobenzenesulfonyl chlorides (2-NosCls) being the key building blocks. Fmoc-α-amino acids were immobilized on Wang resin and transformed to the cor...
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| Veröffentlicht in: | ACS combinatorial science 2014-05, Vol.16 (5), p.221-224 |
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| container_title | ACS combinatorial science |
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| creator | McMaster, Claire Fülöpová, Veronika Popa, Igor Grepl, Martin Soural, Miroslav |
| description | Simple solid-phase synthesis of 3,10-dihydro-2H-benzo[e]imidazo[1,2-b][1,2,4]thiadiazin-2-one 5,5-dioxides is described, with Fmoc-α-amino acids and 2-nitrobenzenesulfonyl chlorides (2-NosCls) being the key building blocks. Fmoc-α-amino acids were immobilized on Wang resin and transformed to the corresponding 2-nitrobenzenesulfonamides in two steps. After reduction of the nitro group, Fmoc-thioureas were synthesized followed by cyclization of the 1,2,4-benzothiadiazine-1,1-dioxide scaffold with diisopropylcarbodiimide (DIC). Cleavage of the Fmoc protecting group followed by spontaneous cyclative cleavage gave the target products in excellent crude purity. |
| doi_str_mv | 10.1021/co400119c |
| format | Article |
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Fmoc-α-amino acids were immobilized on Wang resin and transformed to the corresponding 2-nitrobenzenesulfonamides in two steps. After reduction of the nitro group, Fmoc-thioureas were synthesized followed by cyclization of the 1,2,4-benzothiadiazine-1,1-dioxide scaffold with diisopropylcarbodiimide (DIC). 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Cleavage of the Fmoc protecting group followed by spontaneous cyclative cleavage gave the target products in excellent crude purity.</description><subject>Amino Acids - chemistry</subject><subject>Chlorides</subject><subject>Cleavage</subject><subject>Combinatorial analysis</subject><subject>Combinatorial Chemistry Techniques</subject><subject>Cyclization</subject><subject>Fibrinolytic Agents - chemical synthesis</subject><subject>Fibrinolytic Agents - chemistry</subject><subject>Fluorenes - chemistry</subject><subject>Guanidines</subject><subject>Polymers</subject><subject>Quinazolines - chemical synthesis</subject><subject>Quinazolines - chemistry</subject><subject>Scaffolds</subject><subject>Solid-Phase Synthesis Techniques</subject><subject>Spontaneous</subject><subject>Sulfinic Acids - chemical synthesis</subject><subject>Sulfinic Acids - chemistry</subject><subject>Synthesis</subject><issn>2156-8952</issn><issn>2156-8944</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMtKQzEQhoMottQufAHpRtDF0dxzsizFGxQUquuQ5tKekp7UpGfRtzeltSvB2cww8_EPfABcI_iAIEaPJlIIEZLmDPQxYryqJaXnp5nhHhjmvIKlKJWYw0vQw1RghljdB3wWQ2Orj6XObjTbtduly00eRT8at3qRXDmWfRd8bHdhvwtx0bl8BS68DtkNj30Avp6fPiev1fT95W0ynlaa0HpbGVl7L6X0nBCHNDG65pRg7YXW0gpLoafeGAkdxhoTboSxdk5tPWfea0vIANwdcjcpfpe_W7VusnEh6NbFLiskOIaMMoH-RxlHkguIcUHvD6hJMefkvNqkZq3TTiGo9lLVSWphb46x3Xzt7In8VViA2wOgTVar2KXiKP8R9APVlHyr</recordid><startdate>20140512</startdate><enddate>20140512</enddate><creator>McMaster, Claire</creator><creator>Fülöpová, Veronika</creator><creator>Popa, Igor</creator><creator>Grepl, Martin</creator><creator>Soural, Miroslav</creator><general>American Chemical Society</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>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20140512</creationdate><title>Solid-Phase Synthesis of Anagrelide Sulfonyl Analogues</title><author>McMaster, Claire ; Fülöpová, Veronika ; Popa, Igor ; Grepl, Martin ; Soural, Miroslav</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-c98ff999f633e1a3ca86432af7aa9d7d40f4fcc90e22a236c7cddb4d8b5ffad33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Amino Acids - chemistry</topic><topic>Chlorides</topic><topic>Cleavage</topic><topic>Combinatorial analysis</topic><topic>Combinatorial Chemistry Techniques</topic><topic>Cyclization</topic><topic>Fibrinolytic Agents - chemical synthesis</topic><topic>Fibrinolytic Agents - chemistry</topic><topic>Fluorenes - chemistry</topic><topic>Guanidines</topic><topic>Polymers</topic><topic>Quinazolines - chemical synthesis</topic><topic>Quinazolines - chemistry</topic><topic>Scaffolds</topic><topic>Solid-Phase Synthesis Techniques</topic><topic>Spontaneous</topic><topic>Sulfinic Acids - chemical synthesis</topic><topic>Sulfinic Acids - chemistry</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>McMaster, Claire</creatorcontrib><creatorcontrib>Fülöpová, Veronika</creatorcontrib><creatorcontrib>Popa, Igor</creatorcontrib><creatorcontrib>Grepl, Martin</creatorcontrib><creatorcontrib>Soural, Miroslav</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>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>ACS combinatorial science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>McMaster, Claire</au><au>Fülöpová, Veronika</au><au>Popa, Igor</au><au>Grepl, Martin</au><au>Soural, Miroslav</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Solid-Phase Synthesis of Anagrelide Sulfonyl Analogues</atitle><jtitle>ACS combinatorial science</jtitle><addtitle>ACS Comb. 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| source | MEDLINE; ACS Publications |
| subjects | Amino Acids - chemistry Chlorides Cleavage Combinatorial analysis Combinatorial Chemistry Techniques Cyclization Fibrinolytic Agents - chemical synthesis Fibrinolytic Agents - chemistry Fluorenes - chemistry Guanidines Polymers Quinazolines - chemical synthesis Quinazolines - chemistry Scaffolds Solid-Phase Synthesis Techniques Spontaneous Sulfinic Acids - chemical synthesis Sulfinic Acids - chemistry Synthesis |
| title | Solid-Phase Synthesis of Anagrelide Sulfonyl Analogues |
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