- Direct Syn Addition of Two Silicon Atoms to a C≡C Triple Bond by Si?Si Bond Activation: Access to Reactive Disilylated Olefins
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A catalytic intramolecular silapalladation of alkynes affords, in good yields and stereoselectively, syn-disilylated heterocycles of different chemical structure and size. When applied to silylethers, this reaction leads to vinylic silanols that undergo a rhodium-catalyzed addition to activated olefins, providing the oxa-Heck or oxa-Michael products, depending on the reaction conditions.
- Ahmad, Maha,Gaumont, Annie-Claude,Durandetti, Muriel,Maddaluno, Jacques
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supporting information
p. 2464 - 2468
(2017/02/23)
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- Enantioselective synthesis of boron-substituted quaternary carbon stereogenic centers through NHC-catalyzed conjugate additions of (pinacolato)boron units to enones
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The first examples of Lewis base catalyzed enantioselective boryl conjugate additions (BCAs) that generate products containing boron-substituted quaternary carbon stereogenic centers are disclosed. Reactions are performed in the presence of 1.0-5.0 mol %
- Radomkit, Suttipol,Hoveyda, Amir H.
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supporting information
p. 3387 - 3391
(2014/04/03)
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- Bioactive prenylated phenyl derivatives derived from marine natural products: Novel scaffolds for the design of BACE inhibitors
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Abnormal accumulation of neurotoxic beta-amyloid peptides (Aβ) is a key factor in the development of Alzheimer's disease (AD) and strategies to reduce Aβ production constitute an active field of research for the development of novel therapeutic agents for the treatment of AD. In particular, β-secretase-1 (BACE-1) has been a prime target for modulating Aβ production although obtaining drug-like BACE-1 inhibitors has proven to be highly challenging. Here we report the isolation and biochemical characterization of a marine natural product, the prenylated hydroxybenzoic acid 1, with BACE-1 inhibitory activity and ability to decrease Aβ production in cell-based assays. Synthesis and biological activity of a number of new synthetic analogues are also reported, as well as initial structure-activity relationship (SAR) analysis on this chemical family. Hence, these compounds constitute novel scaffolds from which more potent and selective BACE-1 inhibitors could be designed as potential therapeutic agents for the treatment of Alzheimer's disease.
- López-Ogalla, Javier,García-Palomero, Esther,Sánchez-Quesada, Jorge,Rubio, Laura,Delgado, Elena,García, Pablo,Medina, Miguel,Castro, Ana,Mu?oz, Pilar
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p. 474 - 488
(2014/04/17)
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- PHENYL-PRENYL DERIVATIVES, OF MARINE AND SYNTHETIC ORIGIN, FOR THE TREATMENT OF COGNITIVE, NEURODEGENERATIVE OR NEURONAL DISEASES OR DISORDERS
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The present invention is related to a family of phenyl-prenyl derivatives of formula (I), and to their use in the treatment of cognitive, neurodegenerative or neuronal diseases or disorders, such as Alzheimer's disease or Parkinson's Disease. The present
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Page/Page column 31
(2009/10/09)
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- CHEMOTHERAPEUTIC FLAVONOIDS, AND SYNTHESES THEREOF
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Substituted flavonoid compounds, and pharmaceutical formulations of flavonoid compounds are described. Also described are processes for preparing flavonid compounds, as are methods for treating cancer in mammals using the described flavonoid compounds or pharmaceutical formulations thereof.
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Page/Page column 18; 29
(2008/12/06)
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- Synthesis and biological evaluation of (±)-abyssinone II and its analogues as aromatase inhibitors for chemoprevention of breast cancer
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An efficient and economical synthesis of the naturally occurring aromatase inhibitor abyssinone II was performed. The synthesis features an optimized aromatic prenylation reaction in which an arylcopper intermediate is reacted with prenyl bromide to afford a key intermediate that was converted to a prenylated aromatic aldehyde. Condensation of the aldehyde with an o-hydroxyacetophenone under Claisen-Schmidt conditions afforded a chalcone that was deprotected and cyclized in the presence of sodium acetate in refluxing ethanol to afford (±)-abyssinone II. The synthesis proved to be versatile enough to provide an array of abyssinone II derivatives that were evaluated as aromatase inhibitors. Methylation of the 4′-hydroxyl group of (±)-abyssinone II resulted in a significant increase in aromatase inhibitory activity, and further smaller increases in activity resulted from the methylation of the 7-hydroxyl group and removal of the prenyl side chain. As a result of these structural changes, the most active flavanone of the series was 20 times more potent than (±)-abyssinone II (IC50 40.95 μM).
- Maiti, Arup,Cuendet, Muriel,Croy, Vicki L.,Endringer, Denise C.,Pezzuto, John M.,Cushman, Mark
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p. 2799 - 2806
(2008/02/06)
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- Pyridine derivatives, their production and use
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Pyridine derivatives of the formula STR1 wherein the ring A stands for an optionally further substituted benzene ring; the ring B stands for an optionally substituted pyridine ring; Q stands for hydroxyl group, or OQ 1 or Q 1 wherein Q 1 stands for an optionally substituted aliphatic hydrocarbon group; and n denotes 0 or 1, or their salts, which have potassium.channel opening activity and are useful as therapeutic agents of circulatory diseases such as angina pectoris, hypertension, etc.
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