858644-34-5Relevant academic research and scientific papers
Acyl/aroyl Meldrum's acid as an enol surrogate for the direct organocatalytic synthesis of α,β-unsaturated ketones
Khopade, Tushar M.,Warghude, Prakash K.,Mete, Trimbak B.,Bhat, Ramakrishna G.
, p. 197 - 200 (2018/12/13)
The operationally simple, robust and straightforward organocatalytic protocol is developed for the synthesis of E-selective α,β-unsaturated ketones. The method utilizes simple and easily accessible starting materials such as Meldrum's acid, carboxylic acid, aldehyde and simple bifunctional amine catalyst. The tandem organocatalytic process utilizes acyl/aroyl Meldrum's acid as an enol surrogate for the effective Doebner-Knoevenagel type condensation reactions. A wide variety of aldehydes, carboxylic acids and base sensitive functional groups are well tolerated under the mild reaction conditions.
Michael acceptor-containing coenzyme a analogues as inhibitors of the atypical coenzyme a disulfide reductase from staphylococcus aureus
Van Der Westhuyzen, Renier,Strauss, Erick
supporting information; experimental part, p. 12853 - 12855 (2010/11/05)
Coenzyme A (CoA) analogues containing α,β-unsaturated ester, ketone, and sulfone moieties were prepared by chemo-enzymatic synthesis as inhibitors of coenzyme A disulfide reductase (CoADR), a proven and as yet unexploited drug target in Staphylococcus aureus. Among these Michael acceptor-containing CoA analogues, which were designed to target CoADR's single essential active site cysteine for conjugate addition, a phenyl vinyl sulfone-containing analogue showed the most potent inhibition with a competitive Ki of ～40 nM, and time-dependent inactivation with a second-order rate of inactivation constant of ～40 000 s -1?M-1. Our results suggest that electrophilic substrate analogues should be considered as potential inhibitors of other medicinally relevant disulfide reductase enzymes.
