Novel Steroidal[17,16-<i>d</i>]pyrimidines Derived from Epiandrosterone and Androsterone: Synthesis, Characterization and Configuration-Activity Relationships
Two series of novel steroidal[17,16-<i>d</i>]pyrimidines derived from natural epiandrosterone and androsterone were designed and synthesized, and these compounds were screened for their potential anticancer activities. The preliminary bioassay indicated that some of these prepared compou...
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| Format: | Article |
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MDPI AG
2023-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/6/2691 |
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| author | Fei Yang Fang Liu Yong Min Liqiao Shi Manli Liu Kaimei Wang Shaoyong Ke Yan Gong Ziwen Yang |
| author_facet | Fei Yang Fang Liu Yong Min Liqiao Shi Manli Liu Kaimei Wang Shaoyong Ke Yan Gong Ziwen Yang |
| author_sort | Fei Yang |
| collection | DOAJ |
| description | Two series of novel steroidal[17,16-<i>d</i>]pyrimidines derived from natural epiandrosterone and androsterone were designed and synthesized, and these compounds were screened for their potential anticancer activities. The preliminary bioassay indicated that some of these prepared compounds exhibited significantly good cytotoxic activities against human gastric cancer (SGC-7901), lung cancer (A549), and hepatocellular liver carcinoma (HepG2) cell lines compared with 5-fluorouracil (5-FU), epiandrosterone, and androsterone. Especially the respective pairs from epiandrosterone and androsterone showed significantly different inhibitory activities, and the possible configuration-activity relationships have also been summarized and discussed based on kinase assay and molecular docking, which indicated that the inhibition activities of these steroidal[17,16-<i>d</i>]pyrimidines might obviously be affected by the configuration of the hydroxyl group in the part of the steroidal scaffold. |
| first_indexed | 2024-03-11T06:07:03Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T06:07:03Z |
| publishDate | 2023-03-01 |
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| spelling | doaj.art-19df5c494cbb4af6981c819f6e108a5a2023-11-17T12:53:50ZengMDPI AGMolecules1420-30492023-03-01286269110.3390/molecules28062691Novel Steroidal[17,16-<i>d</i>]pyrimidines Derived from Epiandrosterone and Androsterone: Synthesis, Characterization and Configuration-Activity RelationshipsFei Yang0Fang Liu1Yong Min2Liqiao Shi3Manli Liu4Kaimei Wang5Shaoyong Ke6Yan Gong7Ziwen Yang8College of Life Sciences, Wuhan University, Wuhan 430072, ChinaKey Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, ChinaKey Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, ChinaKey Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, ChinaKey Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, ChinaKey Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, ChinaKey Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, ChinaKey Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, ChinaCollege of Life Sciences, Wuhan University, Wuhan 430072, ChinaTwo series of novel steroidal[17,16-<i>d</i>]pyrimidines derived from natural epiandrosterone and androsterone were designed and synthesized, and these compounds were screened for their potential anticancer activities. The preliminary bioassay indicated that some of these prepared compounds exhibited significantly good cytotoxic activities against human gastric cancer (SGC-7901), lung cancer (A549), and hepatocellular liver carcinoma (HepG2) cell lines compared with 5-fluorouracil (5-FU), epiandrosterone, and androsterone. Especially the respective pairs from epiandrosterone and androsterone showed significantly different inhibitory activities, and the possible configuration-activity relationships have also been summarized and discussed based on kinase assay and molecular docking, which indicated that the inhibition activities of these steroidal[17,16-<i>d</i>]pyrimidines might obviously be affected by the configuration of the hydroxyl group in the part of the steroidal scaffold.https://www.mdpi.com/1420-3049/28/6/2691epiandrosteroneandrosteronesteroidal[17,16-<i>d</i>]pyrimidinessynthesisbioactivitymolecular docking |
| spellingShingle | Fei Yang Fang Liu Yong Min Liqiao Shi Manli Liu Kaimei Wang Shaoyong Ke Yan Gong Ziwen Yang Novel Steroidal[17,16-<i>d</i>]pyrimidines Derived from Epiandrosterone and Androsterone: Synthesis, Characterization and Configuration-Activity Relationships Molecules epiandrosterone androsterone steroidal[17,16-<i>d</i>]pyrimidines synthesis bioactivity molecular docking |
| title | Novel Steroidal[17,16-<i>d</i>]pyrimidines Derived from Epiandrosterone and Androsterone: Synthesis, Characterization and Configuration-Activity Relationships |
| title_full | Novel Steroidal[17,16-<i>d</i>]pyrimidines Derived from Epiandrosterone and Androsterone: Synthesis, Characterization and Configuration-Activity Relationships |
| title_fullStr | Novel Steroidal[17,16-<i>d</i>]pyrimidines Derived from Epiandrosterone and Androsterone: Synthesis, Characterization and Configuration-Activity Relationships |
| title_full_unstemmed | Novel Steroidal[17,16-<i>d</i>]pyrimidines Derived from Epiandrosterone and Androsterone: Synthesis, Characterization and Configuration-Activity Relationships |
| title_short | Novel Steroidal[17,16-<i>d</i>]pyrimidines Derived from Epiandrosterone and Androsterone: Synthesis, Characterization and Configuration-Activity Relationships |
| title_sort | novel steroidal 17 16 i d i pyrimidines derived from epiandrosterone and androsterone synthesis characterization and configuration activity relationships |
| topic | epiandrosterone androsterone steroidal[17,16-<i>d</i>]pyrimidines synthesis bioactivity molecular docking |
| url | https://www.mdpi.com/1420-3049/28/6/2691 |
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