Organocatalytic Enantioselective Friedel–Crafts Reaction of Phenanthrenequinones and Indoles
An efficient stereoselective synthesis of 10-hydroxy-10-(1<i>H</i>-indol-3-yl)-9-(10<i>H</i>)-phenanthrene derivatives was realized through an organocatalyzed Friedel–Crafts reaction of phenanthrenequinones and indoles using a (<i>S</i>,<i>S</i>)-dimet...
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2025-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/1/172 |
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| author | Yan Jin Yuhong Sun Yue Yu Jiao Zhao Mingshan Zheng Liming Wang Ying Jin |
| author_facet | Yan Jin Yuhong Sun Yue Yu Jiao Zhao Mingshan Zheng Liming Wang Ying Jin |
| author_sort | Yan Jin |
| collection | DOAJ |
| description | An efficient stereoselective synthesis of 10-hydroxy-10-(1<i>H</i>-indol-3-yl)-9-(10<i>H</i>)-phenanthrene derivatives was realized through an organocatalyzed Friedel–Crafts reaction of phenanthrenequinones and indoles using a (<i>S</i>,<i>S</i>)-dimethylaminocyclohexyl-squaramide as the catalyst. Under the optimized conditions, the desired chiral products were obtained in good yields (73–90%) with moderate to high ee values (up to 97% ee). Two pairs of synthesized enantiomers were subjected to evaluation of their antiproliferative activities on four types of human cancer cell lines and one human umbilical vein endothelial cell line using the CCK-8 assay. The results indicated that stereoselectivity had obvious impacts on biological activity. (<i>S</i>)-<b>4g</b> was found to have optimal cytotoxicity against the A549 cell line and a good safety profile for human normal cells, which was better than the inhibitory activity of the positive control drug (doxorubicin). |
| format | Article |
| id | doaj-art-2487edb37bf14b4487aa33c190b6013b |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-2487edb37bf14b4487aa33c190b6013b2025-01-10T13:19:06ZengMDPI AGMolecules1420-30492025-01-0130117210.3390/molecules30010172Organocatalytic Enantioselective Friedel–Crafts Reaction of Phenanthrenequinones and IndolesYan Jin0Yuhong Sun1Yue Yu2Jiao Zhao3Mingshan Zheng4Liming Wang5Ying Jin6Department of Pharmacy, Jilin Medical University, Jilin 132013, ChinaDepartment of Pharmacy, Jilin Medical University, Jilin 132013, ChinaSchool of Pharmaceutical Sciences, Yanbian University, Yanji 133000, ChinaDepartment of Pharmacy, Jilin Medical University, Jilin 132013, ChinaSchool of Pharmaceutical Sciences, Yanbian University, Yanji 133000, ChinaDepartment of Pharmacy, Jilin Medical University, Jilin 132013, ChinaDepartment of Pharmacy, Jilin Medical University, Jilin 132013, ChinaAn efficient stereoselective synthesis of 10-hydroxy-10-(1<i>H</i>-indol-3-yl)-9-(10<i>H</i>)-phenanthrene derivatives was realized through an organocatalyzed Friedel–Crafts reaction of phenanthrenequinones and indoles using a (<i>S</i>,<i>S</i>)-dimethylaminocyclohexyl-squaramide as the catalyst. Under the optimized conditions, the desired chiral products were obtained in good yields (73–90%) with moderate to high ee values (up to 97% ee). Two pairs of synthesized enantiomers were subjected to evaluation of their antiproliferative activities on four types of human cancer cell lines and one human umbilical vein endothelial cell line using the CCK-8 assay. The results indicated that stereoselectivity had obvious impacts on biological activity. (<i>S</i>)-<b>4g</b> was found to have optimal cytotoxicity against the A549 cell line and a good safety profile for human normal cells, which was better than the inhibitory activity of the positive control drug (doxorubicin).https://www.mdpi.com/1420-3049/30/1/172enantioselectiveFriedel–Crafts reactionorganocatalysisphenanthrenequinonesindolesCCK-8 assay |
| spellingShingle | Yan Jin Yuhong Sun Yue Yu Jiao Zhao Mingshan Zheng Liming Wang Ying Jin Organocatalytic Enantioselective Friedel–Crafts Reaction of Phenanthrenequinones and Indoles Molecules enantioselective Friedel–Crafts reaction organocatalysis phenanthrenequinones indoles CCK-8 assay |
| title | Organocatalytic Enantioselective Friedel–Crafts Reaction of Phenanthrenequinones and Indoles |
| title_full | Organocatalytic Enantioselective Friedel–Crafts Reaction of Phenanthrenequinones and Indoles |
| title_fullStr | Organocatalytic Enantioselective Friedel–Crafts Reaction of Phenanthrenequinones and Indoles |
| title_full_unstemmed | Organocatalytic Enantioselective Friedel–Crafts Reaction of Phenanthrenequinones and Indoles |
| title_short | Organocatalytic Enantioselective Friedel–Crafts Reaction of Phenanthrenequinones and Indoles |
| title_sort | organocatalytic enantioselective friedel crafts reaction of phenanthrenequinones and indoles |
| topic | enantioselective Friedel–Crafts reaction organocatalysis phenanthrenequinones indoles CCK-8 assay |
| url | https://www.mdpi.com/1420-3049/30/1/172 |
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