Synthesis and analgesic activity evaluation of derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid
The synthesis of new derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid is described. Starting 2-{[5-aryl-2-oxofuran-3(2H)-ylidene]amino}thiophene-3-carboxylic acids were obtained by intramolecular cyclisation of substituted 4-aryl...
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Ural Federal University
2021-11-01
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| Series: | Chimica Techno Acta |
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| Online Access: | https://chimicatechnoacta.ru/article/view/5434 |
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| author | Alena I. Siutkina Ramiz R. Makhmudov Daria A. Shipilovskikh |
| author_facet | Alena I. Siutkina Ramiz R. Makhmudov Daria A. Shipilovskikh |
| author_sort | Alena I. Siutkina |
| collection | DOAJ |
| description | The synthesis of new derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid is described. Starting 2-{[5-aryl-2-oxofuran-3(2H)-ylidene]amino}thiophene-3-carboxylic acids were obtained by intramolecular cyclisation of substituted 4-aryl-4-oxo-2-thienylaminobut-2-enoic acids in acetic anhydride. New derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acids were obtained via decyclization reaction of 2-{[5-aryl-2-oxofuran-3(2H)-ylidene]amino}thiophene-3-carboxylic acids. The structure of the compounds obtained was confirmed by the 1H and 13C NMR spectroscopy, IR spectrometry and elemental analysis methods. Analgesic activity of new compounds has been studied by the “hot plate” method on outbred white mice of both sexes with intraperitoneal injection. It was found that derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid possess analgesic effect exceeding the effect of the comparison drug metamizole. |
| format | Article |
| id | doaj-art-4cb8ea4ab360480a817d2d622a7f70bc |
| institution | OA Journals |
| issn | 2411-1414 |
| language | English |
| publishDate | 2021-11-01 |
| publisher | Ural Federal University |
| record_format | Article |
| series | Chimica Techno Acta |
| spelling | doaj-art-4cb8ea4ab360480a817d2d622a7f70bc2025-08-20T02:38:39ZengUral Federal UniversityChimica Techno Acta2411-14142021-11-018410.15826/chimtech.2021.8.4.044112Synthesis and analgesic activity evaluation of derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acidAlena I. Siutkina0Ramiz R. Makhmudov1Daria A. Shipilovskikh2Perm State University; Perm State Pharmaceutical AcademyPerm State University; Federal Scientific Center for Medical and Preventive Health Risk Management TechnologiesPerm National Research Polytechnic UniversityThe synthesis of new derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid is described. Starting 2-{[5-aryl-2-oxofuran-3(2H)-ylidene]amino}thiophene-3-carboxylic acids were obtained by intramolecular cyclisation of substituted 4-aryl-4-oxo-2-thienylaminobut-2-enoic acids in acetic anhydride. New derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acids were obtained via decyclization reaction of 2-{[5-aryl-2-oxofuran-3(2H)-ylidene]amino}thiophene-3-carboxylic acids. The structure of the compounds obtained was confirmed by the 1H and 13C NMR spectroscopy, IR spectrometry and elemental analysis methods. Analgesic activity of new compounds has been studied by the “hot plate” method on outbred white mice of both sexes with intraperitoneal injection. It was found that derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid possess analgesic effect exceeding the effect of the comparison drug metamizole.https://chimicatechnoacta.ru/article/view/5434analgesic activity, gewald reaction, 2,4-dioxobutanoic acids, 3-(thiophen-2-yl)iminofuran-2(3h)-one |
| spellingShingle | Alena I. Siutkina Ramiz R. Makhmudov Daria A. Shipilovskikh Synthesis and analgesic activity evaluation of derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid Chimica Techno Acta analgesic activity, gewald reaction, 2,4-dioxobutanoic acids, 3-(thiophen-2-yl)iminofuran-2(3h)-one |
| title | Synthesis and analgesic activity evaluation of derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid |
| title_full | Synthesis and analgesic activity evaluation of derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid |
| title_fullStr | Synthesis and analgesic activity evaluation of derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid |
| title_full_unstemmed | Synthesis and analgesic activity evaluation of derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid |
| title_short | Synthesis and analgesic activity evaluation of derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid |
| title_sort | synthesis and analgesic activity evaluation of derivatives of 2 1 4 dioxo 1 amino 4 arylbutyl 2 en 2 yl amino 4 5 6 7 tetrahydrobenzo b thiophene 3 carboxylic acid |
| topic | analgesic activity, gewald reaction, 2,4-dioxobutanoic acids, 3-(thiophen-2-yl)iminofuran-2(3h)-one |
| url | https://chimicatechnoacta.ru/article/view/5434 |
| work_keys_str_mv | AT alenaisiutkina synthesisandanalgesicactivityevaluationofderivativesof214dioxo1amino4arylbutyl2en2ylamino4567tetrahydrobenzobthiophene3carboxylicacid AT ramizrmakhmudov synthesisandanalgesicactivityevaluationofderivativesof214dioxo1amino4arylbutyl2en2ylamino4567tetrahydrobenzobthiophene3carboxylicacid AT dariaashipilovskikh synthesisandanalgesicactivityevaluationofderivativesof214dioxo1amino4arylbutyl2en2ylamino4567tetrahydrobenzobthiophene3carboxylicacid |