Ethyl 5-Oxo-5-(((12-oxoindolo[2,1-<i>b</i>]quinazolin-6(12<i>H</i>)-ylidene)amino)oxy)pentanoate
Indolo[2,1-<i>b</i>]quinazolin-6,12-dione (tryptanthrin) derivatives present important types of nitrogen-containing heterocyclic compounds which are useful intermediate products in organic synthesis and have potential pharmaceutical applications. The new ethyl 5-oxo-5-(((12-oxoindolo[2,1...
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| Format: | Article |
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MDPI AG
2022-09-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2022/4/M1451 |
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| author | Anastasia R. Kovrizhina Alina A. Kolpakova Andrei A. Kuznetzov Andrei I. Khlebnikov |
| author_facet | Anastasia R. Kovrizhina Alina A. Kolpakova Andrei A. Kuznetzov Andrei I. Khlebnikov |
| author_sort | Anastasia R. Kovrizhina |
| collection | DOAJ |
| description | Indolo[2,1-<i>b</i>]quinazolin-6,12-dione (tryptanthrin) derivatives present important types of nitrogen-containing heterocyclic compounds which are useful intermediate products in organic synthesis and have potential pharmaceutical applications. The new ethyl 5-oxo-5-(((12-oxoindolo[2,1-<i>b</i>]quinazolin-6(12<i>H</i>)-ylidene)amino)oxy)pentanoate (Compound <b>2</b>) was synthesized. Compound <b>2</b> is the first example of a tryptanthrin derivative containing a dicarboxylic acid residue in the side chain. The <i>Z</i>,<i>E</i>-isomerism of Compound <b>2</b> was investigated by DFT calculations. Bioavailability was evaluated in silico using ADME predictions. According to the ADME results, Compound <b>2</b> is potentially highly bioavailable and has the prospective to be used as the main component for the development of anti-inflammatory drugs. |
| first_indexed | 2024-03-09T16:03:14Z |
| format | Article |
| id | doaj.art-5ed924f8c5da447b89d3440055a79d68 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-09T16:03:14Z |
| publishDate | 2022-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-5ed924f8c5da447b89d3440055a79d682023-11-24T16:53:30ZengMDPI AGMolbank1422-85992022-09-0120224M145110.3390/M1451Ethyl 5-Oxo-5-(((12-oxoindolo[2,1-<i>b</i>]quinazolin-6(12<i>H</i>)-ylidene)amino)oxy)pentanoateAnastasia R. Kovrizhina0Alina A. Kolpakova1Andrei A. Kuznetzov2Andrei I. Khlebnikov3Kizhner Research Center, Tomsk Polytechnic University, 634050 Tomsk, RussiaKizhner Research Center, Tomsk Polytechnic University, 634050 Tomsk, RussiaKizhner Research Center, Tomsk Polytechnic University, 634050 Tomsk, RussiaKizhner Research Center, Tomsk Polytechnic University, 634050 Tomsk, RussiaIndolo[2,1-<i>b</i>]quinazolin-6,12-dione (tryptanthrin) derivatives present important types of nitrogen-containing heterocyclic compounds which are useful intermediate products in organic synthesis and have potential pharmaceutical applications. The new ethyl 5-oxo-5-(((12-oxoindolo[2,1-<i>b</i>]quinazolin-6(12<i>H</i>)-ylidene)amino)oxy)pentanoate (Compound <b>2</b>) was synthesized. Compound <b>2</b> is the first example of a tryptanthrin derivative containing a dicarboxylic acid residue in the side chain. The <i>Z</i>,<i>E</i>-isomerism of Compound <b>2</b> was investigated by DFT calculations. Bioavailability was evaluated in silico using ADME predictions. According to the ADME results, Compound <b>2</b> is potentially highly bioavailable and has the prospective to be used as the main component for the development of anti-inflammatory drugs.https://www.mdpi.com/1422-8599/2022/4/M1451dicarboxylic acid derivativetryptanthrinisomerismDFTADME |
| spellingShingle | Anastasia R. Kovrizhina Alina A. Kolpakova Andrei A. Kuznetzov Andrei I. Khlebnikov Ethyl 5-Oxo-5-(((12-oxoindolo[2,1-<i>b</i>]quinazolin-6(12<i>H</i>)-ylidene)amino)oxy)pentanoate Molbank dicarboxylic acid derivative tryptanthrin isomerism DFT ADME |
| title | Ethyl 5-Oxo-5-(((12-oxoindolo[2,1-<i>b</i>]quinazolin-6(12<i>H</i>)-ylidene)amino)oxy)pentanoate |
| title_full | Ethyl 5-Oxo-5-(((12-oxoindolo[2,1-<i>b</i>]quinazolin-6(12<i>H</i>)-ylidene)amino)oxy)pentanoate |
| title_fullStr | Ethyl 5-Oxo-5-(((12-oxoindolo[2,1-<i>b</i>]quinazolin-6(12<i>H</i>)-ylidene)amino)oxy)pentanoate |
| title_full_unstemmed | Ethyl 5-Oxo-5-(((12-oxoindolo[2,1-<i>b</i>]quinazolin-6(12<i>H</i>)-ylidene)amino)oxy)pentanoate |
| title_short | Ethyl 5-Oxo-5-(((12-oxoindolo[2,1-<i>b</i>]quinazolin-6(12<i>H</i>)-ylidene)amino)oxy)pentanoate |
| title_sort | ethyl 5 oxo 5 12 oxoindolo 2 1 i b i quinazolin 6 12 i h i ylidene amino oxy pentanoate |
| topic | dicarboxylic acid derivative tryptanthrin isomerism DFT ADME |
| url | https://www.mdpi.com/1422-8599/2022/4/M1451 |
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