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Development of Novel Antiatherogenic Biaryls: Design, Synthesis, and Reactivity.

Abstract : On the basis of the 5,5'-bisvanillin scaffold, a series of compounds has been synthesized presenting symmetric or dissymmetric frames on each phenolic moiety. These frames are alpha,beta-unsaturated (fluoro)phosphonate and/or alpha,beta-unsaturated hydrazone(s) formed by coupling aldehydic with isoniazid or hydralazine. All compounds were tested for their ability to inhibit cell-mediated low-density lipoprotein oxidation. Oxidized low-density lipoprotein induced cytotoxicity was also evaluated along with the carbonyl scavenger properties of selected compounds. The most efficient agents were found to be those possessing at least one hydralazinone frame, with the most potent being the symmetrical compound: 4,4'-dihydroxy-3,3'-dimethoxy-5,5'-biphenyl-1,1'-(diphthalazin-1-yl)methylhydrazone hydrochloride.
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https://www.hal.inserm.fr/inserm-00279925
Contributor : Florence Bedos-Belval <>
Submitted on : Thursday, May 15, 2008 - 4:41:16 PM
Last modification on : Friday, January 17, 2020 - 3:38:03 PM
Long-term archiving on: : Friday, November 25, 2016 - 10:47:12 PM

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Mélanie Delomenède, Florence Bedos-Belval, Hubert Duran, Cécile Vindis, Michel Baltas, et al.. Development of Novel Antiatherogenic Biaryls: Design, Synthesis, and Reactivity.. Journal of Medicinal Chemistry, American Chemical Society, 2008, 51 (11), pp.3171-3181. ⟨10.1021/jm7014793⟩. ⟨inserm-00279925⟩

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