Antinociceptive activities of alpha-truxillic acid and beta-truxinic acid derivatives

Biological & Pharmaceutical Bulletin
Yu-Ming ChiShinobu Sakurada

Abstract

Our recent study demonstrated that the dimeric structure of alpha-truxillic acid derivatives played an important role in the expression of their anti-inflammatory activities. In the present report, to investigate the correlation between the structure and anti-inflammatory activity, alpha-truxillic acid (1) and its derivatives (2-6), beta-truxinic acid (7) and its derivatives (8-10) were prepared, and their activities were evaluated in the formalin test. All compounds showed only weak or no activities against the neurogenic pain response, but demonstrated significant activities against the inflammatory pain response induced by formalin. The highest anti-inflammatory activities were observed for alpha-truxillic acid (1) and its derivative 4,4'-dihydroxy-alpha-truxillic acid (2). In addition, alpha-truxillic acid (1) and its derivative, alpha-truxillic acid bis(p-nitrophenyl)ester (5), showed higher anti-inflammatory activities than beta-truxinic acid (7) and the corresponding derivative (10). Furthermore, free carboxylic acids (1, 2) showed higher activities than their dimethyl esters (3, 4) and bis(p-nitrophenyl)ester (5). These results confirmed that the alpha-formation of dimeric structure and the free carboxylic acid were als...Continue Reading

Citations

Mar 2, 2006·Biological & Pharmaceutical Bulletin·Yu-Ming ChiShinobu Sakurada
Jun 20, 2020·Beilstein Journal of Organic Chemistry·Esteban P UrriolabeitiaCarlos Cativiela
Mar 19, 2008·Journal of Asian Natural Products Research·Dae-Young LeeNam-In Baek
Sep 3, 2010·The Journal of Organic Chemistry·Marwan W Ghosn, Christian Wolf
Nov 20, 2018·The Journal of Organic Chemistry·Isabellar F S MarraGiovanni Wilson Amarante
Dec 6, 2018·Journal of the American Chemical Society·Santiago CañellasMiquel À Pericàs
Sep 2, 2021·The Journal of Organic Chemistry·Bilge Banu YagciYunus Emre Türkmen

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