Discovery of highly potent analgesic activity of isopulegol-derived (2R,4aR,7R,8aR)-4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol
| Autor: | Nariman F. Salakhutdinov, Dina V. Korchagina, Tatyana G. Tolstikova, E. V. Nazimova, Irina V. Il'ina, Alla Pavlova, Oksana S. Mikhalchenko, Konstantin P. Volcho |
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| Rok vydání: | 2016 |
| Předmět: |
Analgesic effect
010405 organic chemistry Stereochemistry Organic Chemistry Analgesic chemistry.chemical_element 010402 general chemistry Ring (chemistry) 01 natural sciences Sulfur 0104 chemical sciences Terpene chemistry.chemical_compound Montmorillonite chemistry Oral administration General Pharmacology Toxicology and Pharmaceutics Hot plate test |
| Zdroj: | Medicinal Chemistry Research. 25:1369-1383 |
| ISSN: | 1554-8120 1054-2523 |
| DOI: | 10.1007/s00044-016-1573-3 |
| Popis: | A large set of chiral heterocyclic compounds with the octahydro-2H-chromene scaffold was first obtained by a reaction of (−)-isopulegol and (+)-neoisopulegol with furan-2-carbaldehyde, thiophene-2-carbaldehyde and their derivatives and isomers in the presence of montmorillonite K10 clay. Most of the (−)-isopulegol-derived compounds exhibited a significant analgesic activity in the acetic acid-induced writhing test. Compound 3b obtained by a reaction of (−)-isopulegol with thiophene-2-carbaldehyde demonstrated a significant analgesic effect in this test within 15 min after oral administration at the dose of 1 mg/kg and retains the effect for at least 24 h. Compound 3b exhibited analgesic activity in the hot plate test also. A change in the sulfur atom position in the aromatic ring was found to lead to the effect reversal in the hot plate test. |
| Databáze: | OpenAIRE |
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