Synthesis and analgesic activity of 1,3,5-trisubstituted pyrazoles containing a diterpenoid moiety

Synthesis and analgesic activity of 1,3,5-trisubstituted pyrazoles containing a diterpenoid moiety

Conjugates of terpenoids with 1,3,5-trisubstituted pyrazoles were synthesized by the cross-coupling of methyl 16-(2-chloro-2-oxoacetyl)labdatrienoate with terminal arylacetylenes via the Castro—Stephens reaction and heterocyclization of arylalkyne-1,2-diones with arylhydr-azines. The structure of on...

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Veröffentlicht in:Russian chemical bulletin 2020-03, Vol.69 (3), p.537-546
Hauptverfasser: Mironov, M. E., Poltanovich, A. I., Rybalova, T. V., Dolgikh, M. P., Tolstikova, T. G., Shults, E. E.
Format: Artikel
Sprache:eng
Schlagworte:
Analgesics
Azines
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Cross coupling
Full Articles
Inorganic Chemistry
Irritation
Organic Chemistry
Reaction products
Terpenes
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Zusammenfassung:Conjugates of terpenoids with 1,3,5-trisubstituted pyrazoles were synthesized by the cross-coupling of methyl 16-(2-chloro-2-oxoacetyl)labdatrienoate with terminal arylacetylenes via the Castro—Stephens reaction and heterocyclization of arylalkyne-1,2-diones with arylhydr-azines. The structure of one reaction product was established by X-ray diffraction. The conditions for the formation of furanolabdanoid arylalkyne-1,2-diones were found. The newly synthesized pyrazoles exhibit analgesic activity in a model of chemical irritation.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-020-2795-6