Synthesis and anticancer activity of 2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)-N-arylacetamides
Search for new biologically active compounds includes the directed design of molecules based on the so-called structural blocks – usually the privileged (structures, to which the 4-thiazolidinone cycle belongs. Therefore the development of methods for the synthesis of small "drug-like" mol...
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| Format: | Article |
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Zaporizhzhia State Medical and Pharmaceutical University
2020-08-01
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| Series: | Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki |
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| Online Access: | http://pharmed.zsmu.edu.ua/article/view/207100/207462 |
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| author | A. P. Kryshchyshyn-Dylevych |
| author_facet | A. P. Kryshchyshyn-Dylevych |
| author_sort | A. P. Kryshchyshyn-Dylevych |
| collection | DOAJ |
| description | Search for new biologically active compounds includes the directed design of molecules based on the so-called structural blocks – usually the privileged (structures, to which the 4-thiazolidinone cycle belongs. Therefore the development of methods for the synthesis of small "drug-like" molecules from 2-cyanomethylidene-4-thiazolidinone group as well as the study of their biological profile is an urgent task for modern medicinal chemistry.
Aim. To design and to the synthesis of novel 5-ylidene derivatives of 2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)-N-arylacetamides. Study of the antitumor activity of synthesized compounds.
Materials and methods. Organic synthesis, study of the spectral characteristics of obtained 4-thiazolidinones (1H and 13C NMR spectroscopy, LC- MS spectrometry). In vitro antitumor activity study according to the DTP Program of the National Cancer Institute (USA).
Results. A number of 5-substituted 2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)-N-arylacetamide derivatives had been synthesized. The structure and purity of the synthesized compounds were confirmed by the methods of elemental analysis, 1H, 13C NMR spectroscopy and LC-MS. The antitumor activity of some of the synthesized compounds was investigated on a panel of 59 human tumor cell lines representing nine neoplastic diseases.
Conclusions. Based on the C5 modification of the methylene group of the 4-thiazolidinone cycle, the target 5-ylidene and 5-aminomethylene-2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)-N-arylacetamides had been synthesized. A hit-compound 2-cyano-2-[5-[(4-methoxyphenyl)methylene]-4-oxo-3-phenylthiazolidin-2-ylidene]-N-arylacetamide was identified that selectively inhibited the growth of some cell lines of CNS, kidney and breast cancers. |
| format | Article |
| id | doaj-art-df2682e78d2148b591bb784599160dea |
| institution | DOAJ |
| issn | 2306-8094 2409-2932 |
| language | English |
| publishDate | 2020-08-01 |
| publisher | Zaporizhzhia State Medical and Pharmaceutical University |
| record_format | Article |
| series | Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki |
| spelling | doaj-art-df2682e78d2148b591bb784599160dea2025-08-20T02:50:56ZengZaporizhzhia State Medical and Pharmaceutical UniversityAktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki2306-80942409-29322020-08-0113219420110.14739/2409-2932.2020.2.207100Synthesis and anticancer activity of 2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)-N-arylacetamidesA. P. Kryshchyshyn-Dylevych0https://orcid.org/0000-0002-8713-7020Danylo Halytsky Lviv National Medical University, UkraineSearch for new biologically active compounds includes the directed design of molecules based on the so-called structural blocks – usually the privileged (structures, to which the 4-thiazolidinone cycle belongs. Therefore the development of methods for the synthesis of small "drug-like" molecules from 2-cyanomethylidene-4-thiazolidinone group as well as the study of their biological profile is an urgent task for modern medicinal chemistry. Aim. To design and to the synthesis of novel 5-ylidene derivatives of 2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)-N-arylacetamides. Study of the antitumor activity of synthesized compounds. Materials and methods. Organic synthesis, study of the spectral characteristics of obtained 4-thiazolidinones (1H and 13C NMR spectroscopy, LC- MS spectrometry). In vitro antitumor activity study according to the DTP Program of the National Cancer Institute (USA). Results. A number of 5-substituted 2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)-N-arylacetamide derivatives had been synthesized. The structure and purity of the synthesized compounds were confirmed by the methods of elemental analysis, 1H, 13C NMR spectroscopy and LC-MS. The antitumor activity of some of the synthesized compounds was investigated on a panel of 59 human tumor cell lines representing nine neoplastic diseases. Conclusions. Based on the C5 modification of the methylene group of the 4-thiazolidinone cycle, the target 5-ylidene and 5-aminomethylene-2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)-N-arylacetamides had been synthesized. A hit-compound 2-cyano-2-[5-[(4-methoxyphenyl)methylene]-4-oxo-3-phenylthiazolidin-2-ylidene]-N-arylacetamide was identified that selectively inhibited the growth of some cell lines of CNS, kidney and breast cancers.http://pharmed.zsmu.edu.ua/article/view/207100/2074624-thiazolidinonesknoevenagel condensationenaminesantitumor activity |
| spellingShingle | A. P. Kryshchyshyn-Dylevych Synthesis and anticancer activity of 2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)-N-arylacetamides Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki 4-thiazolidinones knoevenagel condensation enamines antitumor activity |
| title | Synthesis and anticancer activity of 2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)-N-arylacetamides |
| title_full | Synthesis and anticancer activity of 2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)-N-arylacetamides |
| title_fullStr | Synthesis and anticancer activity of 2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)-N-arylacetamides |
| title_full_unstemmed | Synthesis and anticancer activity of 2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)-N-arylacetamides |
| title_short | Synthesis and anticancer activity of 2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)-N-arylacetamides |
| title_sort | synthesis and anticancer activity of 2 cyano 2 4 oxo 3 phenylthiazolidin 2 ylidene n arylacetamides |
| topic | 4-thiazolidinones knoevenagel condensation enamines antitumor activity |
| url | http://pharmed.zsmu.edu.ua/article/view/207100/207462 |
| work_keys_str_mv | AT apkryshchyshyndylevych synthesisandanticanceractivityof2cyano24oxo3phenylthiazolidin2ylidenenarylacetamides |