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Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes Full article

Journal Medicinal Chemistry Research
ISSN: 1054-2523 , E-ISSN: 1554-8120
Output data Year: 2020, Volume: 29, Number: 4, Pages: 738-747 Pages count : 10 DOI: 10.1007/s00044-020-02518-3
Tags Terpene; Chromene; Heterocyclic compounds; Analgesic activity; Acetic acid-induced writhing test; Hot plate test
Authors Il'ina Irina 1 , Morozova Ekaterina 1 , Pavlova Alla 1 , Korchagina Dina 1 , Tolstikova Tat'yana 1 , Volcho Konstantin 1,2 , Salakhutdinov Nariman 1,2
Affiliations
1 (Данные Web of science) Russian Acad Sci, Novosibirsk Inst Organ Chem, Siberian Branch, Lavrentjev Av 9, Novosibirsk 630090, Russia
2 (Данные Web of science) Novosibirsk State Univ, Pirogova St 1, Novosibirsk 630090, Russia

Abstract: New hexahydro-2H-chromenes were synthesized by reactions of monoterpenoid (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aliphatic ketones in the presence of montmorillonite clay H+-K10. The compounds formed and isolated as a pair of diastereoisomers were evaluated for their analgesic activity in vivo. It was found that the analgesic activity of (4aR,8R,8aR)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydrospiro[chromene-2,1MODIFIER LETTER PRIME-cyclohexane]-4,8-diol 8b significantly exceeds (two orders of magnitude higher) the activity of diclofenac sodium in the acetic acid-induced writhing test. It has low acute toxicity and is very promising for further development.
Cite: Il'ina I. , Morozova E. , Pavlova A. , Korchagina D. , Tolstikova T. , Volcho K. , Salakhutdinov N.
Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes
Medicinal Chemistry Research. 2020. V.29. N4. P.738-747. DOI: 10.1007/s00044-020-02518-3 WOS Scopus РИНЦ
Dates:
Published online: Feb 7, 2020
Published print: Apr 1, 2020
Identifiers:
Web of science WOS:000515974600001
Scopus 2-s2.0-85079194094
Elibrary 43261218
OpenAlex W3004615305
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