Synthesis and biological activity of new rhodanine-triazole conjugates with 2-(2,6-dichlorophenylamino)benzyl moiety in the molecules
Molecular design of “drug-like” molecules based on the combination of a fragment of non-steroidal anti-inflammatory drug diclofenac with a pharmacologically attractive 1,2,4-triazole and 4-thiazolidinone “structural matrices” in one molecule is an effective approach in modern medical chemistry. A...
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| Format: | Article |
| Language: | English |
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Zaporozhye State Medical 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/207024/207467 |
| _version_ | 1818157683987972096 |
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| author | Yu. L. Shepeta O. M. Roman I. O. Nektiehaiev R. B. Lesyk |
| author_facet | Yu. L. Shepeta O. M. Roman I. O. Nektiehaiev R. B. Lesyk |
| author_sort | Yu. L. Shepeta |
| collection | DOAJ |
| description | Molecular design of “drug-like” molecules based on the combination of a fragment of non-steroidal anti-inflammatory drug diclofenac with a pharmacologically attractive 1,2,4-triazole and 4-thiazolidinone “structural matrices” in one molecule is an effective approach in modern medical chemistry.
Aim. Synthesis of new rhodanine-triazole hybrid molecules (conjugates) with 2- (2,6-dichlorophenylamino) benzyl moiety and evaluation of their biological activity.
Materials and methods. The method of rhodanine-triazoles synthesis was elaborated. The structures of the synthesized compounds were confirmed by elemental analysis, NMR spectroscopy, and LCMS. The anti-exudative activity of the compounds was investigated in a rat carrageenan edema model, and the antitumor effect was studied in vitro at a concentration of 10-5 M on 60 cancer cell lines (DTP NCI Program).
Results. Novel 2-{5-[2-(2,6-dichlorophenylamino)-benzyl]-4H-1,2,4-triazol-3-ylsulfanyl}-N-(4-oxo-2-thioxothiazolidin-3-yl)-acetamides and their 5-arylidene derivatives were synthesized/ Among these derivatives hit compounds with anti-inflammatory and anticancer activity against cell lines of melanoma, leukemia, non-small cell lung cancer, colon cancer, CNS cancer, ovarian cancer, renal cancer, and breast cancer were identified.
Conclusion. The molecular design of rhodanine-triazole hybrid molecules based on diclofenac is an effective approach to the search for novel anti-inflammatory and antitumor agents. |
| first_indexed | 2024-12-11T15:18:06Z |
| format | Article |
| id | doaj.art-48106d6d10454a50b72d2a32efa22254 |
| institution | Directory Open Access Journal |
| issn | 2306-8094 2409-2932 |
| language | English |
| last_indexed | 2024-12-11T15:18:06Z |
| publishDate | 2020-08-01 |
| publisher | Zaporozhye State Medical University |
| record_format | Article |
| series | Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki |
| spelling | doaj.art-48106d6d10454a50b72d2a32efa222542022-12-22T01:00:29ZengZaporozhye State Medical UniversityAktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki2306-80942409-29322020-08-0113220621310.14739/2409-2932.2020.2.207024Synthesis and biological activity of new rhodanine-triazole conjugates with 2-(2,6-dichlorophenylamino)benzyl moiety in the moleculesYu. L. Shepeta0O. M. Roman1I. O. Nektiehaiev2R. B. Lesyk3Vinnytsia National Pirogov Memorial Medical University, UkraineDanylo Halytsky Lviv National Medical University, UkraineDanylo Halytsky Lviv National Medical University, UkraineDanylo Halytsky Lviv National Medical University, UkraineMolecular design of “drug-like” molecules based on the combination of a fragment of non-steroidal anti-inflammatory drug diclofenac with a pharmacologically attractive 1,2,4-triazole and 4-thiazolidinone “structural matrices” in one molecule is an effective approach in modern medical chemistry. Aim. Synthesis of new rhodanine-triazole hybrid molecules (conjugates) with 2- (2,6-dichlorophenylamino) benzyl moiety and evaluation of their biological activity. Materials and methods. The method of rhodanine-triazoles synthesis was elaborated. The structures of the synthesized compounds were confirmed by elemental analysis, NMR spectroscopy, and LCMS. The anti-exudative activity of the compounds was investigated in a rat carrageenan edema model, and the antitumor effect was studied in vitro at a concentration of 10-5 M on 60 cancer cell lines (DTP NCI Program). Results. Novel 2-{5-[2-(2,6-dichlorophenylamino)-benzyl]-4H-1,2,4-triazol-3-ylsulfanyl}-N-(4-oxo-2-thioxothiazolidin-3-yl)-acetamides and their 5-arylidene derivatives were synthesized/ Among these derivatives hit compounds with anti-inflammatory and anticancer activity against cell lines of melanoma, leukemia, non-small cell lung cancer, colon cancer, CNS cancer, ovarian cancer, renal cancer, and breast cancer were identified. Conclusion. The molecular design of rhodanine-triazole hybrid molecules based on diclofenac is an effective approach to the search for novel anti-inflammatory and antitumor agents.http://pharmed.zsmu.edu.ua/article/view/207024/207467синтез4н-1 2 4-тріазолроданіндиклофенакпротизапальна активністьпротипухлинна активність |
| spellingShingle | Yu. L. Shepeta O. M. Roman I. O. Nektiehaiev R. B. Lesyk Synthesis and biological activity of new rhodanine-triazole conjugates with 2-(2,6-dichlorophenylamino)benzyl moiety in the molecules Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki синтез 4н-1 2 4-тріазол роданін диклофенак протизапальна активність протипухлинна активність |
| title | Synthesis and biological activity of new rhodanine-triazole conjugates with 2-(2,6-dichlorophenylamino)benzyl moiety in the molecules |
| title_full | Synthesis and biological activity of new rhodanine-triazole conjugates with 2-(2,6-dichlorophenylamino)benzyl moiety in the molecules |
| title_fullStr | Synthesis and biological activity of new rhodanine-triazole conjugates with 2-(2,6-dichlorophenylamino)benzyl moiety in the molecules |
| title_full_unstemmed | Synthesis and biological activity of new rhodanine-triazole conjugates with 2-(2,6-dichlorophenylamino)benzyl moiety in the molecules |
| title_short | Synthesis and biological activity of new rhodanine-triazole conjugates with 2-(2,6-dichlorophenylamino)benzyl moiety in the molecules |
| title_sort | synthesis and biological activity of new rhodanine triazole conjugates with 2 2 6 dichlorophenylamino benzyl moiety in the molecules |
| topic | синтез 4н-1 2 4-тріазол роданін диклофенак протизапальна активність протипухлинна активність |
| url | http://pharmed.zsmu.edu.ua/article/view/207024/207467 |
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