Synthesis and biological evaluation of demethyl-retinoic acids

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  • Wada Akimori
    Laboratory of Bioorganic Chemistry for Life Science, Kobe Pharmaceutical University
  • Tsujimoto Mari
    Laboratory of Bioorganic Chemistry for Life Science, Kobe Pharmaceutical University
  • Chikano Saori
    Laboratory of Bioorganic Chemistry for Life Science, Kobe Pharmaceutical University
  • Matsuura Naomi
    Laboratory of Bioorganic Chemistry for Life Science, Kobe Pharmaceutical University
  • Okano Toshio
    Laboratory of Hygienic Sciences, Kobe Pharmaceutical University
  • Nakagawa Kimie
    Laboratory of Hygienic Sciences, The Faculty of Pharmaceutical Sciences, Kobe Gakuin University

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Other Title
  • 脱メチルレチノイン酸類の合成と生物活性
  • ダツメチルレチノイン サンルイ ノ ゴウセイ ト セイブツ カッセイ

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Abstract

A palladium catalyzed coupling reaction of enol triflates, derived from cyclohexanones, with a tetraenyl stannyl ester in the presence of cesium fuloride afforded 9Z-demethyl retinoates in good yields. These esters were converted to the corresponding acids by basic hydrolysis, and then the biological activities of the synthetized demethyl-retinoic acids were evaluated. All demethyl-retinoic acids had no antiproliferative, differentiation-inducing, and apoptosis-inducing activities. However, all demethyl-retinoic acids showed higher transcriptional activity for the retinoid X receptor responsive element gene than did 9Z-retinoic acid (a natural ligand) and 5-demethyl retinoic acid (3a) exhibited the highest transcriptional activity among all demethyl-retinoic acids.

Journal

  • VITAMINS

    VITAMINS 97 (3), 124-130, 2023-03-25

    THE VITAMIN SOCIETY OF JAPAN

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