Parallel Synthesis of 1H-Pyrazolo[3,4‑d]pyrimidines via Condensation of N‑Pyrazolylamides and Nitriles
A novel parallel medicinal chemistry (PMC)-enabled synthesis of 1H-pyrazolo[3,4-d]pyrimidines employing condensation of easily accessible N-pyrazolylamides and nitriles has been developed. The presented studies describe singleton and library enablements that allowed rapid generation of molecular d...
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| Veröffentlicht in: | ACS combinatorial science 2017-11, Vol.19 (11), p.675-680 |
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| creator | Shah, Akshay A Chenard, Lois K Tucker, Joseph W Helal, Christopher J |
| description | A novel parallel medicinal chemistry (PMC)-enabled synthesis of 1H-pyrazolo[3,4-d]pyrimidines employing condensation of easily accessible N-pyrazolylamides and nitriles has been developed. The presented studies describe singleton and library enablements that allowed rapid generation of molecular diversity to examine C4 and C6 vectors. This chemistry enabled access to challenging alkyl substituents, expanding the overall chemical space beyond that available via typical C(sp2)–C(sp2) coupling and SNAr transformations. Furthermore, monomer group interconversions allowing the use of larger and more diverse amides and carboxylic acids as precursors to nitriles are discussed. |
| doi_str_mv | 10.1021/acscombsci.7b00116 |
| format | Article |
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The presented studies describe singleton and library enablements that allowed rapid generation of molecular diversity to examine C4 and C6 vectors. This chemistry enabled access to challenging alkyl substituents, expanding the overall chemical space beyond that available via typical C(sp2)–C(sp2) coupling and SNAr transformations. Furthermore, monomer group interconversions allowing the use of larger and more diverse amides and carboxylic acids as precursors to nitriles are discussed.</description><identifier>ISSN: 2156-8952</identifier><identifier>EISSN: 2156-8944</identifier><identifier>DOI: 10.1021/acscombsci.7b00116</identifier><identifier>PMID: 28985050</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Amides - chemistry ; Chemistry, Pharmaceutical ; Drug Carriers ; Humans ; Nitriles - chemistry ; Particle Size ; Pyrazoles - chemical synthesis ; Pyrazoles - chemistry ; Pyrimidines - chemical synthesis ; Pyrimidines - chemistry ; Surface Properties</subject><ispartof>ACS combinatorial science, 2017-11, Vol.19 (11), p.675-680</ispartof><rights>Copyright © 2017 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0002-9091-2091 ; 0000-0001-9451-0869</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acscombsci.7b00116$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acscombsci.7b00116$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28985050$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shah, Akshay A</creatorcontrib><creatorcontrib>Chenard, Lois K</creatorcontrib><creatorcontrib>Tucker, Joseph W</creatorcontrib><creatorcontrib>Helal, Christopher J</creatorcontrib><title>Parallel Synthesis of 1H-Pyrazolo[3,4‑d]pyrimidines via Condensation of N‑Pyrazolylamides and Nitriles</title><title>ACS combinatorial science</title><addtitle>ACS Comb. 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Furthermore, monomer group interconversions allowing the use of larger and more diverse amides and carboxylic acids as precursors to nitriles are discussed.</description><subject>Amides - chemistry</subject><subject>Chemistry, Pharmaceutical</subject><subject>Drug Carriers</subject><subject>Humans</subject><subject>Nitriles - chemistry</subject><subject>Particle Size</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrimidines - chemical synthesis</subject><subject>Pyrimidines - chemistry</subject><subject>Surface Properties</subject><issn>2156-8952</issn><issn>2156-8944</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkU1OwzAQhS0EolXpBVigLFmQYjv-yxJVQJGqUglYIWQ5sSNcuXGJE6Sw4gpckZPgqgVmM7P43mjmPQBOEZwgiNGlKkPp10Uo7YQXECLEDsAQI8pSkRNy-DdTPADjEFYwFiE5ZvAYDLDIBYUUDsFqqRrlnHHJQ1-3rybYkPgqQbN02Tfqwzv_nF2Q788v_bLpG7u22tYmJO9WJVNfa1MH1VpfbzWLSO1FvVORjJyqdbKwbWOdCSfgqFIumPG-j8DTzfXjdJbO72_vplfzVCFG25QqXBBOGOY6E5whUyiiYFZhVhHENaog1yWLfxCuqM6NwEJgmCMsCk0rwrMRON_t3TT-rTOhlWsbSuOcqo3vgkQ5EZwKxHBEz_ZoV6yNlpv4oWp6-etPBCY7INotV75r6ni5RFBuM5D_Gch9BtkPWJV7qQ</recordid><startdate>20171113</startdate><enddate>20171113</enddate><creator>Shah, Akshay A</creator><creator>Chenard, Lois K</creator><creator>Tucker, Joseph W</creator><creator>Helal, Christopher J</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>7X8</scope><orcidid>https://orcid.org/0000-0002-9091-2091</orcidid><orcidid>https://orcid.org/0000-0001-9451-0869</orcidid></search><sort><creationdate>20171113</creationdate><title>Parallel Synthesis of 1H-Pyrazolo[3,4‑d]pyrimidines via Condensation of N‑Pyrazolylamides and Nitriles</title><author>Shah, Akshay A ; Chenard, Lois K ; Tucker, Joseph W ; Helal, Christopher J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a165t-5a2b474627d38761eba4a03f26f417d1f07dc626047a5d9e8288209128bd5f473</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Amides - chemistry</topic><topic>Chemistry, Pharmaceutical</topic><topic>Drug Carriers</topic><topic>Humans</topic><topic>Nitriles - chemistry</topic><topic>Particle Size</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrimidines - chemical synthesis</topic><topic>Pyrimidines - chemistry</topic><topic>Surface Properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shah, Akshay A</creatorcontrib><creatorcontrib>Chenard, Lois K</creatorcontrib><creatorcontrib>Tucker, Joseph W</creatorcontrib><creatorcontrib>Helal, Christopher J</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>ACS combinatorial science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shah, Akshay A</au><au>Chenard, Lois K</au><au>Tucker, Joseph W</au><au>Helal, Christopher J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Parallel Synthesis of 1H-Pyrazolo[3,4‑d]pyrimidines via Condensation of N‑Pyrazolylamides and Nitriles</atitle><jtitle>ACS combinatorial science</jtitle><addtitle>ACS Comb. Sci</addtitle><date>2017-11-13</date><risdate>2017</risdate><volume>19</volume><issue>11</issue><spage>675</spage><epage>680</epage><pages>675-680</pages><issn>2156-8952</issn><eissn>2156-8944</eissn><abstract>A novel parallel medicinal chemistry (PMC)-enabled synthesis of 1H-pyrazolo[3,4-d]pyrimidines employing condensation of easily accessible N-pyrazolylamides and nitriles has been developed. The presented studies describe singleton and library enablements that allowed rapid generation of molecular diversity to examine C4 and C6 vectors. This chemistry enabled access to challenging alkyl substituents, expanding the overall chemical space beyond that available via typical C(sp2)–C(sp2) coupling and SNAr transformations. 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| source | ACS Publications; MEDLINE |
| subjects | Amides - chemistry Chemistry, Pharmaceutical Drug Carriers Humans Nitriles - chemistry Particle Size Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrimidines - chemical synthesis Pyrimidines - chemistry Surface Properties |
| title | Parallel Synthesis of 1H-Pyrazolo[3,4‑d]pyrimidines via Condensation of N‑Pyrazolylamides and Nitriles |
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