Synthesis of novel potent cytotoxicy podophyllotoxin-naphthoquinone compounds via microwave-assited multicomponent domino reactions
[Display omitted] •Sixteen new podophyllotoxin analogs containing naphthoquinone moiety on B ring 5a-p were designed and synthesized.•The plausible mechanism for formation of compounds 5a-p was described.•Their anticancer activities against KB, HepG2, SK-Lu-1, and MCF7 cancer cell lines were evaluat...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2021-04, Vol.37, p.127841-127841, Article 127841 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Nguyen Thi, Quynh Giang Le-Nhat-Thuy, Giang Dang Thi, Tuyet Anh Hoang Thi, Phuong Nguyen Tuan, Anh Nguyen Thi, Thu Ha Nguyen, Thanh Tra Nguyen Ha, Thanh Hoang Mai, Ha Nguyen, Tuyen Van |
| description | [Display omitted]
•Sixteen new podophyllotoxin analogs containing naphthoquinone moiety on B ring 5a-p were designed and synthesized.•The plausible mechanism for formation of compounds 5a-p was described.•Their anticancer activities against KB, HepG2, SK-Lu-1, and MCF7 cancer cell lines were evaluated.•Compound 5a, 5d, 5h and 5k were found to be the most promising cytotoxic agent against HepG2 and SK-Lu-1 with IC50 |
| doi_str_mv | 10.1016/j.bmcl.2021.127841 |
| format | Article |
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•Sixteen new podophyllotoxin analogs containing naphthoquinone moiety on B ring 5a-p were designed and synthesized.•The plausible mechanism for formation of compounds 5a-p was described.•Their anticancer activities against KB, HepG2, SK-Lu-1, and MCF7 cancer cell lines were evaluated.•Compound 5a, 5d, 5h and 5k were found to be the most promising cytotoxic agent against HepG2 and SK-Lu-1 with IC50 < 40 nM.
A series of novel podophyllotoxin-naphthoquinone compounds 5a-p were synthesized in good yields using microwave-assisted four-component reactions of 2-hydroxy-1,4-naphthoquinone, aromatic benzaldehydes, tetronic acid and ammonium acetate. All the synthesized compounds were fully characterized by spectral data and evaluated for their cytotoxicity activities against KB, HepG2, Lu1, MCF7, and non-cancerous Hek-293 cell lines. Among 16 new compounds screened, compounds 5a, 5d, 5h, and 5k displayed high potent inhibitory activities with IC50 < 40 nM against HepG2 and SK-Lu-1 cell lines, and showed lower toxicity for non-cancerous Hek-293 cell line, demonstrating the potential importance of these compounds in the development of potential anticancer agents.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2021.127841</identifier><identifier>PMID: 33556568</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Azaanthraquinone ; Cytotoxicic activity ; Four-component reaction ; Microwave-assisted reaction ; Naphthoquinone ; Podophyllotoxin derivatives</subject><ispartof>Bioorganic & medicinal chemistry letters, 2021-04, Vol.37, p.127841-127841, Article 127841</ispartof><rights>2021 Elsevier Ltd</rights><rights>Copyright © 2021 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-3055ef6fbd82e7129a31206f97e7bcd78f18547f63f97ebdf34a7671f35261313</citedby><cites>FETCH-LOGICAL-c356t-3055ef6fbd82e7129a31206f97e7bcd78f18547f63f97ebdf34a7671f35261313</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2021.127841$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33556568$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nguyen Thi, Quynh Giang</creatorcontrib><creatorcontrib>Le-Nhat-Thuy, Giang</creatorcontrib><creatorcontrib>Dang Thi, Tuyet Anh</creatorcontrib><creatorcontrib>Hoang Thi, Phuong</creatorcontrib><creatorcontrib>Nguyen Tuan, Anh</creatorcontrib><creatorcontrib>Nguyen Thi, Thu Ha</creatorcontrib><creatorcontrib>Nguyen, Thanh Tra</creatorcontrib><creatorcontrib>Nguyen Ha, Thanh</creatorcontrib><creatorcontrib>Hoang Mai, Ha</creatorcontrib><creatorcontrib>Nguyen, Tuyen Van</creatorcontrib><title>Synthesis of novel potent cytotoxicy podophyllotoxin-naphthoquinone compounds via microwave-assited multicomponent domino reactions</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
•Sixteen new podophyllotoxin analogs containing naphthoquinone moiety on B ring 5a-p were designed and synthesized.•The plausible mechanism for formation of compounds 5a-p was described.•Their anticancer activities against KB, HepG2, SK-Lu-1, and MCF7 cancer cell lines were evaluated.•Compound 5a, 5d, 5h and 5k were found to be the most promising cytotoxic agent against HepG2 and SK-Lu-1 with IC50 < 40 nM.
A series of novel podophyllotoxin-naphthoquinone compounds 5a-p were synthesized in good yields using microwave-assisted four-component reactions of 2-hydroxy-1,4-naphthoquinone, aromatic benzaldehydes, tetronic acid and ammonium acetate. All the synthesized compounds were fully characterized by spectral data and evaluated for their cytotoxicity activities against KB, HepG2, Lu1, MCF7, and non-cancerous Hek-293 cell lines. Among 16 new compounds screened, compounds 5a, 5d, 5h, and 5k displayed high potent inhibitory activities with IC50 < 40 nM against HepG2 and SK-Lu-1 cell lines, and showed lower toxicity for non-cancerous Hek-293 cell line, demonstrating the potential importance of these compounds in the development of potential anticancer agents.</description><subject>Azaanthraquinone</subject><subject>Cytotoxicic activity</subject><subject>Four-component reaction</subject><subject>Microwave-assisted reaction</subject><subject>Naphthoquinone</subject><subject>Podophyllotoxin derivatives</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kM2KFDEYRYMoTjv6Ai6klm6qzX-qwY0M4w8MuFDBXUglX-g0VUlZSbXW2hc3NT26dBW4nHvJdxB6SfCeYCLfnPb9aIc9xZTsCVUdJ4_QjnDJW8axeIx2-CBx2x349yv0LOcTxoRjzp-iK8aEkEJ2O_T7yxrLEXLITfJNTGcYmikViKWxa0kl_Qp2rYlL03EdhvsgttFMx3JMP5YQU4TGpnFKS3S5OQfTjMHO6ac5Q2tyDgVcMy5DCfdQ3IZdGmuvmcHYElLMz9ETb4YMLx7ea_Tt_e3Xm4_t3ecPn27e3bWWCVlahoUAL33vOgqK0INhhGLpDwpUb53qPOkEV16yLeqdZ9woqYhngkrCCLtGry-701y_DrnoMWQLw2AipCVryjuleDWDK0ovaD0l5xm8nuYwmnnVBOtNvj7pTb7e5OuL_Fp69bC_9CO4f5W_tivw9gJAvfIcYNbZBogWXJjBFu1S-N_-H8WsmkQ</recordid><startdate>20210401</startdate><enddate>20210401</enddate><creator>Nguyen Thi, Quynh Giang</creator><creator>Le-Nhat-Thuy, Giang</creator><creator>Dang Thi, Tuyet Anh</creator><creator>Hoang Thi, Phuong</creator><creator>Nguyen Tuan, Anh</creator><creator>Nguyen Thi, Thu Ha</creator><creator>Nguyen, Thanh Tra</creator><creator>Nguyen Ha, Thanh</creator><creator>Hoang Mai, Ha</creator><creator>Nguyen, Tuyen Van</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20210401</creationdate><title>Synthesis of novel potent cytotoxicy podophyllotoxin-naphthoquinone compounds via microwave-assited multicomponent domino reactions</title><author>Nguyen Thi, Quynh Giang ; Le-Nhat-Thuy, Giang ; Dang Thi, Tuyet Anh ; Hoang Thi, Phuong ; Nguyen Tuan, Anh ; Nguyen Thi, Thu Ha ; Nguyen, Thanh Tra ; Nguyen Ha, Thanh ; Hoang Mai, Ha ; Nguyen, Tuyen Van</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-3055ef6fbd82e7129a31206f97e7bcd78f18547f63f97ebdf34a7671f35261313</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Azaanthraquinone</topic><topic>Cytotoxicic activity</topic><topic>Four-component reaction</topic><topic>Microwave-assisted reaction</topic><topic>Naphthoquinone</topic><topic>Podophyllotoxin derivatives</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nguyen Thi, Quynh Giang</creatorcontrib><creatorcontrib>Le-Nhat-Thuy, Giang</creatorcontrib><creatorcontrib>Dang Thi, Tuyet Anh</creatorcontrib><creatorcontrib>Hoang Thi, Phuong</creatorcontrib><creatorcontrib>Nguyen Tuan, Anh</creatorcontrib><creatorcontrib>Nguyen Thi, Thu Ha</creatorcontrib><creatorcontrib>Nguyen, Thanh Tra</creatorcontrib><creatorcontrib>Nguyen Ha, Thanh</creatorcontrib><creatorcontrib>Hoang Mai, Ha</creatorcontrib><creatorcontrib>Nguyen, Tuyen Van</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nguyen Thi, Quynh Giang</au><au>Le-Nhat-Thuy, Giang</au><au>Dang Thi, Tuyet Anh</au><au>Hoang Thi, Phuong</au><au>Nguyen Tuan, Anh</au><au>Nguyen Thi, Thu Ha</au><au>Nguyen, Thanh Tra</au><au>Nguyen Ha, Thanh</au><au>Hoang Mai, Ha</au><au>Nguyen, Tuyen Van</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of novel potent cytotoxicy podophyllotoxin-naphthoquinone compounds via microwave-assited multicomponent domino reactions</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2021-04-01</date><risdate>2021</risdate><volume>37</volume><spage>127841</spage><epage>127841</epage><pages>127841-127841</pages><artnum>127841</artnum><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
•Sixteen new podophyllotoxin analogs containing naphthoquinone moiety on B ring 5a-p were designed and synthesized.•The plausible mechanism for formation of compounds 5a-p was described.•Their anticancer activities against KB, HepG2, SK-Lu-1, and MCF7 cancer cell lines were evaluated.•Compound 5a, 5d, 5h and 5k were found to be the most promising cytotoxic agent against HepG2 and SK-Lu-1 with IC50 < 40 nM.
A series of novel podophyllotoxin-naphthoquinone compounds 5a-p were synthesized in good yields using microwave-assisted four-component reactions of 2-hydroxy-1,4-naphthoquinone, aromatic benzaldehydes, tetronic acid and ammonium acetate. All the synthesized compounds were fully characterized by spectral data and evaluated for their cytotoxicity activities against KB, HepG2, Lu1, MCF7, and non-cancerous Hek-293 cell lines. Among 16 new compounds screened, compounds 5a, 5d, 5h, and 5k displayed high potent inhibitory activities with IC50 < 40 nM against HepG2 and SK-Lu-1 cell lines, and showed lower toxicity for non-cancerous Hek-293 cell line, demonstrating the potential importance of these compounds in the development of potential anticancer agents.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>33556568</pmid><doi>10.1016/j.bmcl.2021.127841</doi><tpages>1</tpages></addata></record> |
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| subjects | Azaanthraquinone Cytotoxicic activity Four-component reaction Microwave-assisted reaction Naphthoquinone Podophyllotoxin derivatives |
| title | Synthesis of novel potent cytotoxicy podophyllotoxin-naphthoquinone compounds via microwave-assited multicomponent domino reactions |
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