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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.
In particular, it cannot form an electrophilic Michael acceptor that may side-react with biological nucleophiles. [8] DIBO (dibenzocyclooctyne) was developed as a fusion to two aryl rings, resulting in very high strain and a decrease in distortion energies. It was proposed that biaryl substitution increases ring strain and provides conjugation ...
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]
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]
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]
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
In the proposed transition state, one of the thiourea N–H donors is coordinated to the Michael acceptor and will stabilize the negative charge buildup. The basic nitrogen lone pair acts as a hydrogen-bond acceptor to coordinate the nucleophile, but in the transition state acts as a general base to promote the nucleophilic enolate addition.