《Derivatives of cinnamic acid interact with the nucleotide binding site of mitochondrial aldehyde dehydrogenase: effects on the dehydrogenase reaction and stimulation of esterase activity by nucleotides》 was written by Poole, Robert C.; Bowden, Nicola J.; Halestrap, Andrew P.. Reference of 2-Cyano-3-(4-hydroxy-3,5-diisopropylphenyl)acrylamide And the article was included in Biochemical Pharmacology on April 22 ,1993. The article conveys some information:
A wide variety of cinnamic acid derivatives are inhibitors of the low Km mitochondrial aldehyde dehydrogenase. Two of the most potent inhibitors are α-cyano-3,4-dihydroxythiocinnamamide (Ki 0.6 μM) and α-cyano-3,4,5-trihydroxycinnamonitrile (Ki 2.6 μM). With propionaldehyde as substrate the inhibition by these compounds was competitive with respect to NAD+. α-Fluorocinnamate was a much less effective inhibitor of the enzyme, with mixed behavior toward NAD+, but with a major competitive component. These cinnamic acid derivatives were ineffective as inhibitors of the aldehyde dehydrogenase-catalyzed hydrolysis of p-nitrophenyl acetate, but inhibited the ability of NAD+ and NADH to activate this activity. Inhibition of the stimulation of esterase activity was competitive with respect to NAD+ and NADH, and the derived Ki values were the same as for inhibition of dehydrogenase activity. NAD+, but not acetaldehyde, could elute the low Km aldehyde dehydrogenase from α-cyanocinnamate-Sepharose, to which the enzyme binds specifically. The cinnamic acid derivatives have little effect on lactate dehydrogenase, glyceraldehyde-3-phosphate dehydrogenase or a high Km aldehyde dehydrogenase present in rat liver mitochondria. Thus, some cinnamic acid derivatives are potent inhibitors of the low Km aldehyde dehydrogenase, by competing with NAD+/NADH for binding to the enzyme. They are much less effective as inhibitors of other NAD+-dependent dehydrogenases. The experimental part of the paper was very detailed, including the reaction process of 2-Cyano-3-(4-hydroxy-3,5-diisopropylphenyl)acrylamide(cas: 106392-48-7Reference of 2-Cyano-3-(4-hydroxy-3,5-diisopropylphenyl)acrylamide)
2-Cyano-3-(4-hydroxy-3,5-diisopropylphenyl)acrylamide(cas: 106392-48-7) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors.“,” In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Reference of 2-Cyano-3-(4-hydroxy-3,5-diisopropylphenyl)acrylamide
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics