BF<sub>3</sub>-OEt<sub>2</sub> Catalyzed C3-Alkylation of Indole: Synthesis of Indolylsuccinimidesand Their Cytotoxicity Studies
A simple and efficient BF<sub>3</sub>-OEt<sub>2</sub> promoted C3-alkylation of indole has been developed to obtain3-indolylsuccinimidesfrom commercially available indoles and maleimides, with excellent yields under mild reaction conditions. Furthermore, anti-proliferative ac...
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| Format: | Article |
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MDPI AG
2021-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/8/2202 |
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| author | Iqbal N. Shaikh Abdul Rahim Shaikh Faazil Syed Farooq Adil Mohamed E. Assal Mohammad Rafe Hatshan |
| author_facet | Iqbal N. Shaikh Abdul Rahim Shaikh Faazil Syed Farooq Adil Mohamed E. Assal Mohammad Rafe Hatshan |
| author_sort | Iqbal N. Shaikh |
| collection | DOAJ |
| description | A simple and efficient BF<sub>3</sub>-OEt<sub>2</sub> promoted C3-alkylation of indole has been developed to obtain3-indolylsuccinimidesfrom commercially available indoles and maleimides, with excellent yields under mild reaction conditions. Furthermore, anti-proliferative activity of these conjugates was evaluated against HT-29 (Colorectal), Hepg2 (Liver) and A549 (Lung) human cancer cell lines. One of the compounds, <b>3w</b>, having <i>N</i>,<i>N</i>-Dimethylatedindolylsuccinimide is a potent congener amongst the series with IC<sub>50</sub> value 0.02 µM and 0.8 µM against HT-29 and Hepg2 cell lines, respectively, and compound <b>3i</b> was most active amongst the series with IC<sub>50</sub> value 1.5 µM against A549 cells. Molecular docking study and mechanism of reaction have briefly beendiscussed. This method is better than previous reports in view of yield and substrate scope including electron deficient indoles. |
| first_indexed | 2024-03-10T12:25:06Z |
| format | Article |
| id | doaj.art-6afe5aec9d2f40febb49bb76c8cb27e1 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T12:25:06Z |
| publishDate | 2021-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-6afe5aec9d2f40febb49bb76c8cb27e12023-11-21T15:06:06ZengMDPI AGMolecules1420-30492021-04-01268220210.3390/molecules26082202BF<sub>3</sub>-OEt<sub>2</sub> Catalyzed C3-Alkylation of Indole: Synthesis of Indolylsuccinimidesand Their Cytotoxicity StudiesIqbal N. Shaikh0Abdul Rahim1Shaikh Faazil2Syed Farooq Adil3Mohamed E. Assal4Mohammad Rafe Hatshan5Department of Chemistry, Poona College of Arts, Science and Commerce, Camp, Pune 411 001, IndiaDepartment of Chemistry, Poona College of Arts, Science and Commerce, Camp, Pune 411 001, IndiaDepartment of Chemistry, Poona College of Arts, Science and Commerce, Camp, Pune 411 001, IndiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaA simple and efficient BF<sub>3</sub>-OEt<sub>2</sub> promoted C3-alkylation of indole has been developed to obtain3-indolylsuccinimidesfrom commercially available indoles and maleimides, with excellent yields under mild reaction conditions. Furthermore, anti-proliferative activity of these conjugates was evaluated against HT-29 (Colorectal), Hepg2 (Liver) and A549 (Lung) human cancer cell lines. One of the compounds, <b>3w</b>, having <i>N</i>,<i>N</i>-Dimethylatedindolylsuccinimide is a potent congener amongst the series with IC<sub>50</sub> value 0.02 µM and 0.8 µM against HT-29 and Hepg2 cell lines, respectively, and compound <b>3i</b> was most active amongst the series with IC<sub>50</sub> value 1.5 µM against A549 cells. Molecular docking study and mechanism of reaction have briefly beendiscussed. This method is better than previous reports in view of yield and substrate scope including electron deficient indoles.https://www.mdpi.com/1420-3049/26/8/2202C3-alkylationindoleindolylsuccinimidescytotoxicityanticancer |
| spellingShingle | Iqbal N. Shaikh Abdul Rahim Shaikh Faazil Syed Farooq Adil Mohamed E. Assal Mohammad Rafe Hatshan BF<sub>3</sub>-OEt<sub>2</sub> Catalyzed C3-Alkylation of Indole: Synthesis of Indolylsuccinimidesand Their Cytotoxicity Studies Molecules C3-alkylation indole indolylsuccinimides cytotoxicity anticancer |
| title | BF<sub>3</sub>-OEt<sub>2</sub> Catalyzed C3-Alkylation of Indole: Synthesis of Indolylsuccinimidesand Their Cytotoxicity Studies |
| title_full | BF<sub>3</sub>-OEt<sub>2</sub> Catalyzed C3-Alkylation of Indole: Synthesis of Indolylsuccinimidesand Their Cytotoxicity Studies |
| title_fullStr | BF<sub>3</sub>-OEt<sub>2</sub> Catalyzed C3-Alkylation of Indole: Synthesis of Indolylsuccinimidesand Their Cytotoxicity Studies |
| title_full_unstemmed | BF<sub>3</sub>-OEt<sub>2</sub> Catalyzed C3-Alkylation of Indole: Synthesis of Indolylsuccinimidesand Their Cytotoxicity Studies |
| title_short | BF<sub>3</sub>-OEt<sub>2</sub> Catalyzed C3-Alkylation of Indole: Synthesis of Indolylsuccinimidesand Their Cytotoxicity Studies |
| title_sort | bf sub 3 sub oet sub 2 sub catalyzed c3 alkylation of indole synthesis of indolylsuccinimidesand their cytotoxicity studies |
| topic | C3-alkylation indole indolylsuccinimides cytotoxicity anticancer |
| url | https://www.mdpi.com/1420-3049/26/8/2202 |
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