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A Michael reaction is used as a mechanistic step by many covalent inhibitor drugs. Cancer drugs such as ibrutinib, osimertinib, and rociletinib have an acrylamide functional group as a Michael acceptor. The Michael donor on the drug reacts with a Michael acceptor in the active site of an enzyme. This is a viable cancer treatment because the ...
Methyl acrylate is a classic Michael acceptor, which means that it adds nucleophiles at its terminus. For example, in the presence of a base catalyst, it adds hydrogen sulfide to give the thioether: [21] 2 CH 2 CHCO 2 CH 3 + H 2 S → S(CH 2 CH 2 CO 2 CH 3) 2. It is also a good dienophile.
The Stork enamine alkylation involves the addition of an enamine to a Michael acceptor (e.g., an α,β -unsaturated carbonyl compound) or another electrophilic alkylation reagent to give an alkylated iminium product, which is hydrolyzed by dilute aqueous acid to give the alkylated ketone or aldehyde. [1]
The Hauser donor is an aromatic sulfone or methylene sulfoxide with a carboxylic ester group in the ortho position. The Hauser acceptor is a Michael acceptor. In the original Hauser publication ethyl 2-carboxybenzyl phenyl sulfoxide reacts with pent-3-ene-2-one with LDA as a base in THF at −78 °C. [12] Hauser annulation
A nitroalkene behaving as a Michael acceptor in the synthesis of Lycoricidine: [1] [9] Nitroalkene acting as an activated dienophile toward butadiene in a Diels-Alder cycloaddition: [1] [10] The synthesis of pyrrole derivatives via the Barton–Zard reaction: [11] Pericyclic reaction of a nitroalkene yielding an indole: [12]
Suitably soluble Michael acceptors are toxic, because they alkylate DNA by conjugate addition. Such modification induces mutations, which are cytotoxic and carcinogenic. However, glutathione is also able to react with them and for example dimethyl fumarate reacts with it. [citation needed]
Some serve as electron acceptors in electron transport chains such as those in photosynthesis (plastoquinone, phylloquinone), and aerobic respiration . Phylloquinone is also known as vitamin K 1 as it is used by animals to carboxylate certain proteins, which are involved in blood coagulation , bone formation, and other processes.
The reaction applies to a number electrophilic alkenes (Michael acceptors). [2] [3] References This page was last edited on 18 June 2024, at 17:18 (UTC). Text is ...