Synthesis and analgesic activity of new alpha-truxillic acid derivatives with monoterpenoid fragments

Synthesis and analgesic activity of new alpha-truxillic acid derivatives with monoterpenoid fragments Full article

Journal

Medicinal Chemistry Research
ISSN: 1054-2523 , E-ISSN: 1554-8120

Output data

Year: 2016, Volume: 25, Number: 8, Pages: 1608-1615 Pages count : 8 DOI: 10.1007/s00044-016-1593-z

Tags

Terpenoid; Analgesic activity; Acetic acid-induced writhing test; Hot plate test

Authors

Sokolova Anastasiya ^1,2 , Pavlova Alla ¹ , Komarova Nina ¹ , Ardashov Oleg ¹ , Shernyukov Andrey ¹ , Gatilov Yuriy ¹ , Yarovaya Olga ^1,2 , Tolstikova Tat'yana ^1,2 , Salakhutdinov Nariman ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtzov Novosibirsk Inst Organ Chem, Lavrenteva Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova St 2, Novosibirsk 630090, Russia

Novel derivatives of alpha-truxillic acid with a camphor framework were synthesized and evaluated for their in vivo analgesic activity. alpha-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 alpha-truxillic acid. The chemical structures of the synthesized compounds were elucidated by H-1, C-13-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 alpha-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 %.

Sokolova A. , Pavlova A. , Komarova N. , Ardashov O. , Shernyukov A. , Gatilov Y. , Yarovaya O. , Tolstikova T. , Salakhutdinov N.
Synthesis and analgesic activity of new alpha-truxillic acid derivatives with monoterpenoid fragments
Medicinal Chemistry Research. 2016. V.25. N8. P.1608-1615. DOI: 10.1007/s00044-016-1593-z WOS Scopus РИНЦ

Published online:	May 17, 2016
Published print:	Aug 1, 2016

Web of science	WOS:000381207600008
Scopus	2-s2.0-84969221111
Elibrary	1608
OpenAlex	W2403671372