Synthesis and Evaluation of DHMEQ Derivatives with Tertiary Hydroxyl Group Instead of Secondary Hydroxyl Group
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Updated: Aug 4, 2025

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
Yoshimasa Imanishi1, Takuro Terasaki1, Takuya Sano1
1Department of Applied Chemistry, Kogakuin University.
Abstract:
Newly synthesized dehydroxymethyl epoxyquinomycin (DHMEQ) derivatives 6-9, which contain a tertiary hydroxyl group instead of the original secondary hydroxyl group, showed improved solubility in alcohol while maintaining their inhibitory activity against nitric oxide (NO) production, which is used as an indicator of nuclear factor-kappa B (NF-κB) inhibitory activity. We also synthesized a derivative 5 having a cyclopropane ring and a tertiary hydroxyl group and examined its inhibitory activity against NO production. Although it reacted with a nucleophile in a flask, it did not inhibit NO production. The change from a secondary hydroxyl group to a tertiary hydroxyl group contributed to improve the solubility of the compounds while retaining NO inhibitory activity, but had no effect on improving the activity of the cyclopropane form. Compounds in which the secondary hydroxyl group of DHMEQ was converted to a tertiary hydroxyl group would be excellent NF-κB inhibitor candidates because their solubility is improved without decreasing NO inhibitory activity.
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