139488-44-1Relevant articles and documents
Synthesis of Unsymmetrical 1,4-Dicarbonyl Compounds by Photocatalytic Oxidative Radical Additions
Dong, Ya,Li, Ruining,Zhou, Junliang,Sun, Zhankui
supporting information, p. 6387 - 6390 (2021/08/23)
Herein we report a photocatalytic oxidative radical addition reaction for the synthesis of unsymmetrical 1,4-dicarbonyl compounds. This reaction utilizes a desulfurization process to generate electrophilic radicals, which add to α-halogenated alkenes and undergo further oxidation to deliver 1,4-dicarbonyl compounds. This mild and highly efficient method provides a valuable alternative to known strategies.
Site-Selective and Enantioselective α,β,γ-Functionalization of 5-Alkylidenefuran-2(5 H)-ones: A Route to Polycyclic γ-Lactones
Skrzyńska, Anna,Frankowski, Sebastian,Moczulski, Marek,Drelich, Piotr,Albrecht, ?ukasz
supporting information, p. 1248 - 1252 (2019/02/26)
A new strategy for a direct α,β,γ-functionalization of the γ-lactone framework in the corresponding 5-alkylidenefuran-2(5H)-ones is reported. The developed approach is based on a stereocontrolled cascade reaction with 2-mercaptocarbonyl compounds proceedi
Trithiocarbonates as a novel class of HDAC inhibitors: SAR studies, isoenzyme selectivity, and pharmacolozgical profiles
Dehmel, Florian,Weinbrenner, Steffen,Julius, Heiko,Ciossek, Thomas,Maier, Thomas,Stengel, Thomas,Fettis, Kamal,Burkhardt, Carmen,Wieland, Heike,Beckers, Thomas
supporting information; experimental part, p. 3985 - 4001 (2009/05/11)
Inhibitors of histone deacetylases (HDAC) are currently developed for the treatment of cancer. These include compounds with a sulfur containing head group like depsipeptide, alkylthiols, thiocarboxylates, and trithiocarbonates with a carbonyl group in the α-position. In the present investigation, we report on the synthesis and comprehensive SAR analysis of HDAC inhibitors bearing a tri- or dithiocarbonate motif. Such trithiocarbonates are readily accessible from either preformed or in situ prepared α-halogenated methylaryl ketones. A HDAC isotype selectivity and a substrate competitive mode-of-action is shown for defined analogues. Exploration of the head group showed the necessity of the dithio-α-carbonyl motif for potent HDAC inhibition. Highly potent, substrate competitive HDAC6 selective inhibitors were identified (12ac:IC50 = 65 nM and Ki = 110 nM). Trithiocarbonate analogues with an aminoquinoline-substituted pyridinyl-thienoacetyl cap demonstrate a cytotoxicity profile and potency comparable to that of suberoylanilide hydroxamic acid (SAHA) as an approved cancer drug.