Synthesis and analgesic activity of new α-truxillic acid derivatives with monoterpenoid fragments
| Autor: | Olga I. Yarovaya, O. V. Ardashov, Yuriy V. Gatilov, Andrey V. Shernyukov, Tatyana G. Tolstikova, Nina I. Komarova, Alla Pavlova, A. S. Sokolova, Nariman F. Salakhutdinov |
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| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Chemistry Stereochemistry Truxillic acid Organic Chemistry Analgesic 01 natural sciences Medicinal chemistry Terpenoid 0104 chemical sciences Borneol Cyclobutane 010404 medicinal & biomolecular chemistry chemistry.chemical_compound Camphor In vivo General Pharmacology Toxicology and Pharmaceutics Hot plate test |
| Zdroj: | Medicinal Chemistry Research. 25:1608-1615 |
| ISSN: | 1554-8120 1054-2523 |
| DOI: | 10.1007/s00044-016-1593-z |
| Popis: | Novel derivatives of α-truxillic acid with a camphor framework were synthesized and evaluated for their in vivo analgesic activity. α-Truxillic acid derivatives were prepared via solvent-free photocatalyzed [2+2] cyclodimerization of (E)-cinnamic acid. Target compounds were obtained through the substitution of –Cl or –OH groups in α-truxillic acid. The chemical structures of the synthesized compounds were elucidated by 1H, 13C-NMR, and mass spectrometry. Their analgesic activities were evaluated by the acetic acid-induced writhing test and the hot plate method. Compounds 7b and 7f containing the cyclobutane unit and natural fragments at 10 mg/kg exhibited analgesic activity in the acetic acid-induced writhing test, while α-truxillic acid (10 mg/kg, per os) did not show analgesic activity in the test. Intermediate 2 caused a decrease in the writhing with pain inhibition of 28 %. In the hot plate test, borneol showed high analgesic activity with pain inhibition of 60 %. |
| Databáze: | OpenAIRE |
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