- Synthesis of Unsymmetrical 1,4-Dicarbonyl Compounds by Photocatalytic Oxidative Radical Additions
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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.
- Dong, Ya,Li, Ruining,Zhou, Junliang,Sun, Zhankui
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p. 6387 - 6390
(2021/08/23)
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- Site-Selective and Enantioselective α,β,γ-Functionalization of 5-Alkylidenefuran-2(5 H)-ones: A Route to Polycyclic γ-Lactones
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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
- Skrzyńska, Anna,Frankowski, Sebastian,Moczulski, Marek,Drelich, Piotr,Albrecht, ?ukasz
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supporting information
p. 1248 - 1252
(2019/02/26)
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- Intermolecular Phosphite-Mediated Radical Desulfurative Alkene Alkylation Using Thiols
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We report herein the development of a S atom transfer process using triethyl phosphite as the S atom acceptor that allows thiols to serve as precursors of C-centered radicals. A range of functionalized and electronically unbiased alkenes including those containing common heteroatom-based functional groups readily participate in this reductive coupling. This process is driven by the exchange of relatively weak S-H and C-S bonds of aliphatic thiols for C-H, C-C, and S-P bonds of the products formed.
- Lopp, John M.,Schmidt, Valerie A.
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p. 8031 - 8036
(2019/10/19)
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- Br?nsted-base-catalyzed remote cascade reactivity of 2,4-dienones-asymmetric synthesis of tetrahydrothiophenes
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This study demonstrates that the remote cascade functionalization of 2,4-dienones can be realized by employing Br?nsted base catalysis. The developed cascade involving 1,6-addition followed by the intramolecular aldol reaction provides a straightforward a
- Przydacz, Artur,Kowalczyk, Rafa?,Albrecht, ?ukasz
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p. 9566 - 9569
(2017/11/30)
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- Trithiocarbonates as a novel class of HDAC inhibitors: SAR studies, isoenzyme selectivity, and pharmacolozgical profiles
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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.
- Dehmel, Florian,Weinbrenner, Steffen,Julius, Heiko,Ciossek, Thomas,Maier, Thomas,Stengel, Thomas,Fettis, Kamal,Burkhardt, Carmen,Wieland, Heike,Beckers, Thomas
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supporting information; experimental part
p. 3985 - 4001
(2009/05/11)
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- Trithiocarbonates-Exploration of a new head group for HDAC inhibitors
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Inhibition of histone deacetylases class I/II enzymes is a new, promising approach for cancer therapy. In the present study, we disclose a new structural class of HDAC inhibitors with the trithiocarbonate motif. A clear structure-activity-relationship was obtained for the cap-linker motif and the putative Zn2+ complexing head group. Selected analogs display potent inhibition of HDAC enzymatic activity and a cellular potency comparable to that of suberoylanilide hydroxamic acid (SAHA), recently approved for treatment of patients with advanced cutaneous T-cell lymphoma.
- Dehmel, Florian,Ciossek, Thomas,Maier, Thomas,Weinbrenner, Steffen,Schmidt, Beate,Zoche, Martin,Beckers, Thomas
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p. 4746 - 4752
(2008/12/21)
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- A new approach for the conversion of thiohydantoin to hydantoin derivatives
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The reaction of thiohydantoins with 1-(bromoacetyl)benzenes afforded the corresponding hydantoin derivatives and 1-(mercaptoacetyl)benzenes instead of the expected oxoimidazothiazoles.
- Ahluwalia,Mehta,Rawat
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p. 145 - 150
(2007/10/02)
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