Synthesis and Biological Activity of New Derivatives of Isoindoline-1,3-dione as Non-Steroidal Analgesics
A simple method for the synthesis of new derivatives of isoindoline-1,3-dione is developed in this study, which consists of the interaction of <i>N</i>-arylbenzenecarboximidamides with phthalic anhydride in benzene at reflux. It was found that carrying out the reaction without heating le...
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| Format: | Article |
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MDPI AG
2021-11-01
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| Series: | Chemistry Proceedings |
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| Online Access: | https://www.mdpi.com/2673-4583/8/1/99 |
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| author | Yulia A. Trukhanova Denis A. Kolesnik Elena V. Kuvaeva Galina V. Ksenofontova Marina V. Sopova Igor P. Yakovlev |
| author_facet | Yulia A. Trukhanova Denis A. Kolesnik Elena V. Kuvaeva Galina V. Ksenofontova Marina V. Sopova Igor P. Yakovlev |
| author_sort | Yulia A. Trukhanova |
| collection | DOAJ |
| description | A simple method for the synthesis of new derivatives of isoindoline-1,3-dione is developed in this study, which consists of the interaction of <i>N</i>-arylbenzenecarboximidamides with phthalic anhydride in benzene at reflux. It was found that carrying out the reaction without heating leads to the formation of monoacylation products—phthalic acid amides. The structure of the isolated substances was proved using <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy. Acute toxicity and biological activity in silico were studied for all of the obtained compounds using the online programs GUSAR and PASS. For 2-(phenyl(phenylimino)methyl)isoindoline-1,3-dione and 2-((phenyl(phenylimino)methyl)carbamoyl)benzoic acid, an acute toxicity and biological activity in vivo was studied in laboratory mice. It was shown that the results of in silico and in vivo methods are comparable and indicate the low toxicity of the obtained compounds. It was revealed that 2-(phenyl(phenylimino)methyl)isoindoline-1,3-dione has a high analgesic activity, 1.6 times higher than the activity of the reference drug metamizole sodium. |
| first_indexed | 2024-03-11T06:45:51Z |
| format | Article |
| id | doaj.art-92825dfeb4e747b6981ee51411749ef3 |
| institution | Directory Open Access Journal |
| issn | 2673-4583 |
| language | English |
| last_indexed | 2024-03-11T06:45:51Z |
| publishDate | 2021-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemistry Proceedings |
| spelling | doaj.art-92825dfeb4e747b6981ee51411749ef32023-11-17T10:19:26ZengMDPI AGChemistry Proceedings2673-45832021-11-01819910.3390/ecsoc-25-11773Synthesis and Biological Activity of New Derivatives of Isoindoline-1,3-dione as Non-Steroidal AnalgesicsYulia A. Trukhanova0Denis A. Kolesnik1Elena V. Kuvaeva2Galina V. Ksenofontova3Marina V. Sopova4Igor P. Yakovlev5St. Petersburg State University of Chemistry and Pharmacy, Street Prof. Popova 14 Letter A, 197376 St. Petersburg, RussiaSt. Petersburg State University of Chemistry and Pharmacy, Street Prof. Popova 14 Letter A, 197376 St. Petersburg, RussiaSt. Petersburg State University of Chemistry and Pharmacy, Street Prof. Popova 14 Letter A, 197376 St. Petersburg, RussiaSt. Petersburg State University of Chemistry and Pharmacy, Street Prof. Popova 14 Letter A, 197376 St. Petersburg, RussiaSt. Petersburg State University of Chemistry and Pharmacy, Street Prof. Popova 14 Letter A, 197376 St. Petersburg, RussiaSt. Petersburg State University of Chemistry and Pharmacy, Street Prof. Popova 14 Letter A, 197376 St. Petersburg, RussiaA simple method for the synthesis of new derivatives of isoindoline-1,3-dione is developed in this study, which consists of the interaction of <i>N</i>-arylbenzenecarboximidamides with phthalic anhydride in benzene at reflux. It was found that carrying out the reaction without heating leads to the formation of monoacylation products—phthalic acid amides. The structure of the isolated substances was proved using <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy. Acute toxicity and biological activity in silico were studied for all of the obtained compounds using the online programs GUSAR and PASS. For 2-(phenyl(phenylimino)methyl)isoindoline-1,3-dione and 2-((phenyl(phenylimino)methyl)carbamoyl)benzoic acid, an acute toxicity and biological activity in vivo was studied in laboratory mice. It was shown that the results of in silico and in vivo methods are comparable and indicate the low toxicity of the obtained compounds. It was revealed that 2-(phenyl(phenylimino)methyl)isoindoline-1,3-dione has a high analgesic activity, 1.6 times higher than the activity of the reference drug metamizole sodium.https://www.mdpi.com/2673-4583/8/1/99isoindoline-1,3-diones2-(phenyl(phenylimino)methyl)isoindoline-1,3-dioneanalgesic activity<i>N</i>-substituted derivatives of phthalimidenon-steroidal analgesic |
| spellingShingle | Yulia A. Trukhanova Denis A. Kolesnik Elena V. Kuvaeva Galina V. Ksenofontova Marina V. Sopova Igor P. Yakovlev Synthesis and Biological Activity of New Derivatives of Isoindoline-1,3-dione as Non-Steroidal Analgesics Chemistry Proceedings isoindoline-1,3-diones 2-(phenyl(phenylimino)methyl)isoindoline-1,3-dione analgesic activity <i>N</i>-substituted derivatives of phthalimide non-steroidal analgesic |
| title | Synthesis and Biological Activity of New Derivatives of Isoindoline-1,3-dione as Non-Steroidal Analgesics |
| title_full | Synthesis and Biological Activity of New Derivatives of Isoindoline-1,3-dione as Non-Steroidal Analgesics |
| title_fullStr | Synthesis and Biological Activity of New Derivatives of Isoindoline-1,3-dione as Non-Steroidal Analgesics |
| title_full_unstemmed | Synthesis and Biological Activity of New Derivatives of Isoindoline-1,3-dione as Non-Steroidal Analgesics |
| title_short | Synthesis and Biological Activity of New Derivatives of Isoindoline-1,3-dione as Non-Steroidal Analgesics |
| title_sort | synthesis and biological activity of new derivatives of isoindoline 1 3 dione as non steroidal analgesics |
| topic | isoindoline-1,3-diones 2-(phenyl(phenylimino)methyl)isoindoline-1,3-dione analgesic activity <i>N</i>-substituted derivatives of phthalimide non-steroidal analgesic |
| url | https://www.mdpi.com/2673-4583/8/1/99 |
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