1,4-Naphthoquinone Motif in the Synthesis of New Thiopyrano[2,3-<i>d</i>]thiazoles as Potential Biologically Active Compounds
A series of 11-substituted 3,5,10,11-tetrahydro-2<i>H</i>-benzo[6,7]thiochromeno[2,3-<i>d</i>][1,3]thiazole-2,5,10-triones were obtained via <i>hetero</i>-Diels-Alder reaction of 5-alkyl/arylallylidene/-4-thioxo-2-thiazolidinones and 1,4-naphthoquinones. The struc...
| Main Authors: | , , , , , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/21/7575 |
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| author | Andrii Lozynskyi Julia Senkiv Iryna Ivasechko Nataliya Finiuk Olga Klyuchivska Nataliya Kashchak Danylo Lesyk Andriy Karkhut Svyatoslav Polovkovych Oksana Levytska Olexandr Karpenko Assyl Boshkayeva Galiya Sayakova Andrzej Gzella Rostyslav Stoika Roman Lesyk |
| author_facet | Andrii Lozynskyi Julia Senkiv Iryna Ivasechko Nataliya Finiuk Olga Klyuchivska Nataliya Kashchak Danylo Lesyk Andriy Karkhut Svyatoslav Polovkovych Oksana Levytska Olexandr Karpenko Assyl Boshkayeva Galiya Sayakova Andrzej Gzella Rostyslav Stoika Roman Lesyk |
| author_sort | Andrii Lozynskyi |
| collection | DOAJ |
| description | A series of 11-substituted 3,5,10,11-tetrahydro-2<i>H</i>-benzo[6,7]thiochromeno[2,3-<i>d</i>][1,3]thiazole-2,5,10-triones were obtained via <i>hetero</i>-Diels-Alder reaction of 5-alkyl/arylallylidene/-4-thioxo-2-thiazolidinones and 1,4-naphthoquinones. The structures of newly synthesized compounds were established by spectral data and a single-crystal X-ray diffraction analysis. According to U.S. NCI protocols, compounds <b>3.5</b> and <b>3.6</b> were screened for their anticancer activity; 11-Phenethyl-3,11-dihydro-2<i>H</i>-benzo[6,7]thiochromeno[2,3-<i>d</i>]thiazole-2,5,10-trione (<b>3.6</b>) showed pronounced cytotoxic effect on leukemia (Jurkat, THP-1), epidermoid (KB3-1, KBC-1), and colon (HCT116wt, HCT116 p53-/-) cell lines. The cytotoxic action of <b>3.6</b> on p53-deficient colon carcinoma cells was two times weaker than on HCT116wt, and it may be an interesting feature of the mechanism action. |
| first_indexed | 2024-03-09T18:48:26Z |
| format | Article |
| id | doaj.art-e7eca4302d434a269f36d3ec1f75f795 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T18:48:26Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e7eca4302d434a269f36d3ec1f75f7952023-11-24T06:06:30ZengMDPI AGMolecules1420-30492022-11-012721757510.3390/molecules272175751,4-Naphthoquinone Motif in the Synthesis of New Thiopyrano[2,3-<i>d</i>]thiazoles as Potential Biologically Active CompoundsAndrii Lozynskyi0Julia Senkiv1Iryna Ivasechko2Nataliya Finiuk3Olga Klyuchivska4Nataliya Kashchak5Danylo Lesyk6Andriy Karkhut7Svyatoslav Polovkovych8Oksana Levytska9Olexandr Karpenko10Assyl Boshkayeva11Galiya Sayakova12Andrzej Gzella13Rostyslav Stoika14Roman Lesyk15Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, UkraineInstitute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, UkraineInstitute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, UkraineInstitute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, UkraineInstitute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, UkraineInstitute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, UkraineDepartment of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, UkraineDepartment of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Bandera 12, 79013 Lviv, UkraineDepartment of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Bandera 12, 79013 Lviv, UkraineDepartment of Organization and Economics of Pharmacy, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, UkraineEnamine Ltd., 23 Alexandra Matrosova, 01103 Kyiv, UkraineDepartment of Pharmaceutical and Toxicological Chemistry, Pharmacognosy and Botany, Asfendiyarov Kazakh National Medical University, Almaty 050000, KazakhstanDepartment of Pharmaceutical and Toxicological Chemistry, Pharmacognosy and Botany, Asfendiyarov Kazakh National Medical University, Almaty 050000, KazakhstanDepartment of Organic Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan, PolandInstitute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, UkraineDepartment of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, UkraineA series of 11-substituted 3,5,10,11-tetrahydro-2<i>H</i>-benzo[6,7]thiochromeno[2,3-<i>d</i>][1,3]thiazole-2,5,10-triones were obtained via <i>hetero</i>-Diels-Alder reaction of 5-alkyl/arylallylidene/-4-thioxo-2-thiazolidinones and 1,4-naphthoquinones. The structures of newly synthesized compounds were established by spectral data and a single-crystal X-ray diffraction analysis. According to U.S. NCI protocols, compounds <b>3.5</b> and <b>3.6</b> were screened for their anticancer activity; 11-Phenethyl-3,11-dihydro-2<i>H</i>-benzo[6,7]thiochromeno[2,3-<i>d</i>]thiazole-2,5,10-trione (<b>3.6</b>) showed pronounced cytotoxic effect on leukemia (Jurkat, THP-1), epidermoid (KB3-1, KBC-1), and colon (HCT116wt, HCT116 p53-/-) cell lines. The cytotoxic action of <b>3.6</b> on p53-deficient colon carcinoma cells was two times weaker than on HCT116wt, and it may be an interesting feature of the mechanism action.https://www.mdpi.com/1420-3049/27/21/75751,4-naphthoquinones<i>hetero</i>-Diels-Alder reactionthiopyrano[2,3-<i>d</i>]thiazolesX-rayanticancer activitycytotoxicity |
| spellingShingle | Andrii Lozynskyi Julia Senkiv Iryna Ivasechko Nataliya Finiuk Olga Klyuchivska Nataliya Kashchak Danylo Lesyk Andriy Karkhut Svyatoslav Polovkovych Oksana Levytska Olexandr Karpenko Assyl Boshkayeva Galiya Sayakova Andrzej Gzella Rostyslav Stoika Roman Lesyk 1,4-Naphthoquinone Motif in the Synthesis of New Thiopyrano[2,3-<i>d</i>]thiazoles as Potential Biologically Active Compounds Molecules 1,4-naphthoquinones <i>hetero</i>-Diels-Alder reaction thiopyrano[2,3-<i>d</i>]thiazoles X-ray anticancer activity cytotoxicity |
| title | 1,4-Naphthoquinone Motif in the Synthesis of New Thiopyrano[2,3-<i>d</i>]thiazoles as Potential Biologically Active Compounds |
| title_full | 1,4-Naphthoquinone Motif in the Synthesis of New Thiopyrano[2,3-<i>d</i>]thiazoles as Potential Biologically Active Compounds |
| title_fullStr | 1,4-Naphthoquinone Motif in the Synthesis of New Thiopyrano[2,3-<i>d</i>]thiazoles as Potential Biologically Active Compounds |
| title_full_unstemmed | 1,4-Naphthoquinone Motif in the Synthesis of New Thiopyrano[2,3-<i>d</i>]thiazoles as Potential Biologically Active Compounds |
| title_short | 1,4-Naphthoquinone Motif in the Synthesis of New Thiopyrano[2,3-<i>d</i>]thiazoles as Potential Biologically Active Compounds |
| title_sort | 1 4 naphthoquinone motif in the synthesis of new thiopyrano 2 3 i d i thiazoles as potential biologically active compounds |
| topic | 1,4-naphthoquinones <i>hetero</i>-Diels-Alder reaction thiopyrano[2,3-<i>d</i>]thiazoles X-ray anticancer activity cytotoxicity |
| url | https://www.mdpi.com/1420-3049/27/21/7575 |
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