Hybrid Molecules Composed of 2,4-Diamino-1,3,5-triazines and 2-Imino-Coumarins and Coumarins. Synthesis and Cytotoxic Properties
A series of 2-imino-2H-chromen-3-yl-1,3,5-triazine compounds 5–12, which are namely hybrids of 2,4-diamino-1,3,5-triazines and 2-imino-coumarins, was synthesized by reacting 2-(4,6-diamine-1,3,5-triazin-2-yl)acetonitriles 1–4 with 2-hydroxybenzaldehydes. After this, upon heating...
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MDPI AG
2018-07-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/7/1616 |
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| author | Anna Makowska Franciszek Sączewski Patrick J. Bednarski Jarosław Sączewski Łukasz Balewski |
| author_facet | Anna Makowska Franciszek Sączewski Patrick J. Bednarski Jarosław Sączewski Łukasz Balewski |
| author_sort | Anna Makowska |
| collection | DOAJ |
| description | A series of 2-imino-2H-chromen-3-yl-1,3,5-triazine compounds 5–12, which are namely hybrids of 2,4-diamino-1,3,5-triazines and 2-imino-coumarins, was synthesized by reacting 2-(4,6-diamine-1,3,5-triazin-2-yl)acetonitriles 1–4 with 2-hydroxybenzaldehydes. After this, upon heating in aqueous DMF, 2-imino-2H-chromen-3-yl-1,3,5-triazines 10 and 12 were converted into the corresponding 2H-chromen-3-yl-1,3,5-triazines 13 and 14, which are essentially hybrids of 2,4-diamino-1,3,5-triazines and coumarins. The in vitro anticancer activity of the newly prepared compounds was evaluated against five human cancer cell lines: DAN-G, A-427, LCLC-103H, SISO and RT-4. The greatest cytotoxic activity displayed 4-[7-(diethylamino)-2-imino-2H-chromen-3-yl]-6-(4-phenylpiperazin-1-yl)-1,3,5-triazin-2-amine (11, IC50 in the range of 1.51–2.60 μM). |
| first_indexed | 2024-12-21T13:12:57Z |
| format | Article |
| id | doaj.art-41635076fa844c05bf9818efabc180cc |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-21T13:12:57Z |
| publishDate | 2018-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-41635076fa844c05bf9818efabc180cc2022-12-21T19:02:49ZengMDPI AGMolecules1420-30492018-07-01237161610.3390/molecules23071616molecules23071616Hybrid Molecules Composed of 2,4-Diamino-1,3,5-triazines and 2-Imino-Coumarins and Coumarins. Synthesis and Cytotoxic PropertiesAnna Makowska0Franciszek Sączewski1Patrick J. Bednarski2Jarosław Sączewski3Łukasz Balewski4Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gdańsk, 80-416 Gdańsk, PolandDepartment of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gdańsk, 80-416 Gdańsk, PolandDepartment of Pharmaceutical and Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, L.-F.-Jahn Str., D-17489 Greifswald, GermanyDepartment of Organic Chemistry, Faculty of Pharmacy, Medical University of Gdańsk, 80-416 Gdańsk, PolandDepartment of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gdańsk, 80-416 Gdańsk, PolandA series of 2-imino-2H-chromen-3-yl-1,3,5-triazine compounds 5–12, which are namely hybrids of 2,4-diamino-1,3,5-triazines and 2-imino-coumarins, was synthesized by reacting 2-(4,6-diamine-1,3,5-triazin-2-yl)acetonitriles 1–4 with 2-hydroxybenzaldehydes. After this, upon heating in aqueous DMF, 2-imino-2H-chromen-3-yl-1,3,5-triazines 10 and 12 were converted into the corresponding 2H-chromen-3-yl-1,3,5-triazines 13 and 14, which are essentially hybrids of 2,4-diamino-1,3,5-triazines and coumarins. The in vitro anticancer activity of the newly prepared compounds was evaluated against five human cancer cell lines: DAN-G, A-427, LCLC-103H, SISO and RT-4. The greatest cytotoxic activity displayed 4-[7-(diethylamino)-2-imino-2H-chromen-3-yl]-6-(4-phenylpiperazin-1-yl)-1,3,5-triazin-2-amine (11, IC50 in the range of 1.51–2.60 μM).http://www.mdpi.com/1420-3049/23/7/16162-imino-2H-chromen-3-yl-1,3,5-triazines2H-chromen-3-yl-1,3,5-triazines2,4-diamino-1,3,5-triazines2-imino-coumarinscoumarinshybrid moleculesin vitro anticancer activity |
| spellingShingle | Anna Makowska Franciszek Sączewski Patrick J. Bednarski Jarosław Sączewski Łukasz Balewski Hybrid Molecules Composed of 2,4-Diamino-1,3,5-triazines and 2-Imino-Coumarins and Coumarins. Synthesis and Cytotoxic Properties Molecules 2-imino-2H-chromen-3-yl-1,3,5-triazines 2H-chromen-3-yl-1,3,5-triazines 2,4-diamino-1,3,5-triazines 2-imino-coumarins coumarins hybrid molecules in vitro anticancer activity |
| title | Hybrid Molecules Composed of 2,4-Diamino-1,3,5-triazines and 2-Imino-Coumarins and Coumarins. Synthesis and Cytotoxic Properties |
| title_full | Hybrid Molecules Composed of 2,4-Diamino-1,3,5-triazines and 2-Imino-Coumarins and Coumarins. Synthesis and Cytotoxic Properties |
| title_fullStr | Hybrid Molecules Composed of 2,4-Diamino-1,3,5-triazines and 2-Imino-Coumarins and Coumarins. Synthesis and Cytotoxic Properties |
| title_full_unstemmed | Hybrid Molecules Composed of 2,4-Diamino-1,3,5-triazines and 2-Imino-Coumarins and Coumarins. Synthesis and Cytotoxic Properties |
| title_short | Hybrid Molecules Composed of 2,4-Diamino-1,3,5-triazines and 2-Imino-Coumarins and Coumarins. Synthesis and Cytotoxic Properties |
| title_sort | hybrid molecules composed of 2 4 diamino 1 3 5 triazines and 2 imino coumarins and coumarins synthesis and cytotoxic properties |
| topic | 2-imino-2H-chromen-3-yl-1,3,5-triazines 2H-chromen-3-yl-1,3,5-triazines 2,4-diamino-1,3,5-triazines 2-imino-coumarins coumarins hybrid molecules in vitro anticancer activity |
| url | http://www.mdpi.com/1420-3049/23/7/1616 |
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