DABCO-catalyzed one-pot three component synthesis of dihydropyrano[3,2-c]chromene substituted quinazolines and their evaluation towards anticancer activity
The novel carbon–carbon linked dihydropyrano[3,2-c]chromene substituted quinazolines were achieved via DABCO induced Knoevenagel–Michael addition reaction and resulting derivatives were evaluated towards anticancer activity. [Display omitted] A facile DABCO promoted one-pot three component synthesis...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2016-08, Vol.26 (16), p.3973-3977 |
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| container_end_page | 3977 |
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| container_issue | 16 |
| container_start_page | 3973 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 26 |
| creator | Vodnala, Sumathi Bhavani, A.K.D. Kamutam, Ramakrishna Naidu, V.G.M. Promila Prabhakar, Ch |
| description | The novel carbon–carbon linked dihydropyrano[3,2-c]chromene substituted quinazolines were achieved via DABCO induced Knoevenagel–Michael addition reaction and resulting derivatives were evaluated towards anticancer activity. [Display omitted]
A facile DABCO promoted one-pot three component synthesis of a new series of C–C linked bis-heterocycle containing dihydropyrano[c]chromene as highly fused oxa-heteryl group at C-2 position of quinazoline was developed. Quinazoline-2-carbaldehyde, substituted 4-hydroxycoumarin and ethyl cyanoacetate were used as key components in the Knoevenagel–Michael addition reaction to get the titled compounds. These compounds were screened for anti-cancer activity against the breast cancer cell lines of MDA-MB 231, and MDA-MB 453. |
| doi_str_mv | 10.1016/j.bmcl.2016.07.003 |
| format | Article |
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A facile DABCO promoted one-pot three component synthesis of a new series of C–C linked bis-heterocycle containing dihydropyrano[c]chromene as highly fused oxa-heteryl group at C-2 position of quinazoline was developed. Quinazoline-2-carbaldehyde, substituted 4-hydroxycoumarin and ethyl cyanoacetate were used as key components in the Knoevenagel–Michael addition reaction to get the titled compounds. These compounds were screened for anti-cancer activity against the breast cancer cell lines of MDA-MB 231, and MDA-MB 453.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2016.07.003</identifier><identifier>PMID: 27432765</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>4-Hydroxycoumarin ; Anti-cancer ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - metabolism ; Antineoplastic Agents - toxicity ; Benzopyrans - chemistry ; Binding Sites ; Catalysis ; Catalytic Domain ; Cell Line, Tumor ; Cell Survival - drug effects ; DABCO ; Estrogen Receptor alpha - chemistry ; Estrogen Receptor alpha - metabolism ; Humans ; Hydrogen Bonding ; Knoevenagel–Michael reaction ; Molecular Docking Simulation ; Multicomponent reaction ; Piperazines - chemistry ; Quinazoline ; Quinazolines - chemistry ; Thermodynamics</subject><ispartof>Bioorganic & medicinal chemistry letters, 2016-08, Vol.26 (16), p.3973-3977</ispartof><rights>2016 Elsevier Ltd</rights><rights>Copyright © 2016 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-aefe90074855a7be0c5c3745124d977bfc331de81bfafe5b69ddf1e5eb7fc37a3</citedby><cites>FETCH-LOGICAL-c389t-aefe90074855a7be0c5c3745124d977bfc331de81bfafe5b69ddf1e5eb7fc37a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X16307041$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27432765$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Vodnala, Sumathi</creatorcontrib><creatorcontrib>Bhavani, A.K.D.</creatorcontrib><creatorcontrib>Kamutam, Ramakrishna</creatorcontrib><creatorcontrib>Naidu, V.G.M.</creatorcontrib><creatorcontrib>Promila</creatorcontrib><creatorcontrib>Prabhakar, Ch</creatorcontrib><title>DABCO-catalyzed one-pot three component synthesis of dihydropyrano[3,2-c]chromene substituted quinazolines and their evaluation towards anticancer activity</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>The novel carbon–carbon linked dihydropyrano[3,2-c]chromene substituted quinazolines were achieved via DABCO induced Knoevenagel–Michael addition reaction and resulting derivatives were evaluated towards anticancer activity. [Display omitted]
A facile DABCO promoted one-pot three component synthesis of a new series of C–C linked bis-heterocycle containing dihydropyrano[c]chromene as highly fused oxa-heteryl group at C-2 position of quinazoline was developed. Quinazoline-2-carbaldehyde, substituted 4-hydroxycoumarin and ethyl cyanoacetate were used as key components in the Knoevenagel–Michael addition reaction to get the titled compounds. These compounds were screened for anti-cancer activity against the breast cancer cell lines of MDA-MB 231, and MDA-MB 453.</description><subject>4-Hydroxycoumarin</subject><subject>Anti-cancer</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - metabolism</subject><subject>Antineoplastic Agents - toxicity</subject><subject>Benzopyrans - chemistry</subject><subject>Binding Sites</subject><subject>Catalysis</subject><subject>Catalytic Domain</subject><subject>Cell Line, Tumor</subject><subject>Cell Survival - drug effects</subject><subject>DABCO</subject><subject>Estrogen Receptor alpha - chemistry</subject><subject>Estrogen Receptor alpha - metabolism</subject><subject>Humans</subject><subject>Hydrogen Bonding</subject><subject>Knoevenagel–Michael reaction</subject><subject>Molecular Docking Simulation</subject><subject>Multicomponent reaction</subject><subject>Piperazines - chemistry</subject><subject>Quinazoline</subject><subject>Quinazolines - chemistry</subject><subject>Thermodynamics</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkc9u1DAQhy0EokvhBTggHzmQYMdOnEhcyvKvUqVeQEJCyHLsidarxE5tZ1H6KrxsvdrCseppRjO_-Q7zIfSakpIS2rzfl_2kx7LKfUlESQh7gjaUN7xgnNRP0YZ0DSnajv88Qy9i3BNCOeH8OTqrBGeVaOoN-vvp4uP2utAqqXG9BYO9g2L2CaddAMDaT3OeuITj6tIOoo3YD9jY3WqCn9egnP_F3lWF_q13wU_gAMelj8mmJWXazWKduvWjdRCxciZjwQYMBzUuKlnvcPJ_VDDHZbJaOQ0BK53swab1JXo2qDHCq_t6jn58-fx9-624uv56ub24KjRru1QoGKAjRPC2rpXogehaM8FrWnHTCdEPmjFqoKX9oAao-6YzZqBQQy_ySih2jt6euHPwNwvEJCcbNYyjcuCXKGnLBCNt1ZJHREnLWkGrKkerU1QHH2OAQc7BTiqskhJ59Cf38uhPHv1JImT2l4_e3POXfgLz_-SfsBz4cApAfsjBQpBRW8hvMzaATtJ4-xD_DuzDsQQ</recordid><startdate>20160815</startdate><enddate>20160815</enddate><creator>Vodnala, Sumathi</creator><creator>Bhavani, A.K.D.</creator><creator>Kamutam, Ramakrishna</creator><creator>Naidu, V.G.M.</creator><creator>Promila</creator><creator>Prabhakar, Ch</creator><general>Elsevier Ltd</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20160815</creationdate><title>DABCO-catalyzed one-pot three component synthesis of dihydropyrano[3,2-c]chromene substituted quinazolines and their evaluation towards anticancer activity</title><author>Vodnala, Sumathi ; Bhavani, A.K.D. ; Kamutam, Ramakrishna ; Naidu, V.G.M. ; Promila ; Prabhakar, Ch</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-aefe90074855a7be0c5c3745124d977bfc331de81bfafe5b69ddf1e5eb7fc37a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>4-Hydroxycoumarin</topic><topic>Anti-cancer</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - metabolism</topic><topic>Antineoplastic Agents - toxicity</topic><topic>Benzopyrans - chemistry</topic><topic>Binding Sites</topic><topic>Catalysis</topic><topic>Catalytic Domain</topic><topic>Cell Line, Tumor</topic><topic>Cell Survival - drug effects</topic><topic>DABCO</topic><topic>Estrogen Receptor alpha - chemistry</topic><topic>Estrogen Receptor alpha - metabolism</topic><topic>Humans</topic><topic>Hydrogen Bonding</topic><topic>Knoevenagel–Michael reaction</topic><topic>Molecular Docking Simulation</topic><topic>Multicomponent reaction</topic><topic>Piperazines - chemistry</topic><topic>Quinazoline</topic><topic>Quinazolines - chemistry</topic><topic>Thermodynamics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vodnala, Sumathi</creatorcontrib><creatorcontrib>Bhavani, A.K.D.</creatorcontrib><creatorcontrib>Kamutam, Ramakrishna</creatorcontrib><creatorcontrib>Naidu, V.G.M.</creatorcontrib><creatorcontrib>Promila</creatorcontrib><creatorcontrib>Prabhakar, Ch</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>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>Vodnala, Sumathi</au><au>Bhavani, A.K.D.</au><au>Kamutam, Ramakrishna</au><au>Naidu, V.G.M.</au><au>Promila</au><au>Prabhakar, Ch</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>DABCO-catalyzed one-pot three component synthesis of dihydropyrano[3,2-c]chromene substituted quinazolines and their evaluation towards anticancer activity</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2016-08-15</date><risdate>2016</risdate><volume>26</volume><issue>16</issue><spage>3973</spage><epage>3977</epage><pages>3973-3977</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>The novel carbon–carbon linked dihydropyrano[3,2-c]chromene substituted quinazolines were achieved via DABCO induced Knoevenagel–Michael addition reaction and resulting derivatives were evaluated towards anticancer activity. [Display omitted]
A facile DABCO promoted one-pot three component synthesis of a new series of C–C linked bis-heterocycle containing dihydropyrano[c]chromene as highly fused oxa-heteryl group at C-2 position of quinazoline was developed. Quinazoline-2-carbaldehyde, substituted 4-hydroxycoumarin and ethyl cyanoacetate were used as key components in the Knoevenagel–Michael addition reaction to get the titled compounds. These compounds were screened for anti-cancer activity against the breast cancer cell lines of MDA-MB 231, and MDA-MB 453.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>27432765</pmid><doi>10.1016/j.bmcl.2016.07.003</doi><tpages>5</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2016-08, Vol.26 (16), p.3973-3977 |
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| subjects | 4-Hydroxycoumarin Anti-cancer Antineoplastic Agents - chemical synthesis Antineoplastic Agents - metabolism Antineoplastic Agents - toxicity Benzopyrans - chemistry Binding Sites Catalysis Catalytic Domain Cell Line, Tumor Cell Survival - drug effects DABCO Estrogen Receptor alpha - chemistry Estrogen Receptor alpha - metabolism Humans Hydrogen Bonding Knoevenagel–Michael reaction Molecular Docking Simulation Multicomponent reaction Piperazines - chemistry Quinazoline Quinazolines - chemistry Thermodynamics |
| title | DABCO-catalyzed one-pot three component synthesis of dihydropyrano[3,2-c]chromene substituted quinazolines and their evaluation towards anticancer activity |
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