Synthetic Transformations of Higher Terpenoids. 40. Synthesis and Assessment of Analgesic Activity of N-Containing Derivatives of Lambertianic Acid

Synthetic Transformations of Higher Terpenoids. 40. Synthesis and Assessment of Analgesic Activity of N-Containing Derivatives of Lambertianic Acid Full article

Journal

Chemistry of Natural Compounds
ISSN: 0009-3130 , E-ISSN: 1573-8388

Output data

Year: 2021, Volume: 57, Number: 5, Pages: 879-886 Pages count : 8 DOI: 10.1007/s10600-021-03502-y

Tags

diterpenoids; lambertianic acid; 18-norlabdanoids; amines; analgesic activity

Authors

Kharitonov Yu.V. ¹ , Shul'ts E.E. ¹ , Rybalova T.V. ¹ , Pavlova A.V. ¹ , Tolstikova T.G. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Prosp Lavrenteva, Novosibirsk 630090, Russia

New labdanoid derivatives containing hydrophilic substituents (amino, methylamino) in the C-4 position were synthesized via selective transformations of lambertianic acid chloride. A one-pot method was proposed to prepare 16-formyllambertianic acid amide and included selective formylation of lambertianic acid by POCl3 in DMF followed by amidation by aqueous NH4OH. The molecular structure of the compound was studied by an X-ray crystal structure analysis. Analgesic activity in a chemical irritation model was found for newly synthesized 4-amino-18-nor-15,16-epoxylabda-8(17),13,14-triene and 4-(pyrrolidin-1-yl)-18-nor-15,16-epoxylabda-8(17),13,14-triene oxalates and 16-hydroxymethyl)lambertianic acid amide.

Kharitonov Y.V. , Shul'ts E.E. , Rybalova T.V. , Pavlova A.V. , Tolstikova T.G.
Synthetic Transformations of Higher Terpenoids. 40. Synthesis and Assessment of Analgesic Activity of N-Containing Derivatives of Lambertianic Acid
Chemistry of Natural Compounds. 2021. V.57. N5. P.879-886. DOI: 10.1007/s10600-021-03502-y WOS Scopus РИНЦ

Web of science	WOS:000698362000002
Scopus	2-s2.0-85115293477
Elibrary	47047779
OpenAlex	W3200384666