- Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange
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We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C?P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.
- Boehm, Philip,Cacherat, Bastien,Lee, Yong Ho,Martini, Tristano,Morandi, Bill
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supporting information
p. 17211 - 17217
(2021/07/02)
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- Histone Deacetylase Inhibitors and Methods of Use Thereof
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The present invention relates to methods of modulating activity of histone deacetylases (HDACs). The present invention also relates to methods of treating HDAC-associated diseases including, but not limited to, cancers, inflammatory disorders, and neurodegenerative disorders. The present invention also provides novel compounds and compositions thereof and methods of preparation of the same. The present invention also includes methods of inhibiting HDACs, and methods of treating HDAC-associated diseases using the compounds of the invention.
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- TETRAHYDROISOQUINOLIN-2-YL-(QUINAZOLIN-4-YL) METHANONE COMPOUNDS AS CANCER CELL GROWTH INHIBITORS
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Tetrahydroisoquinolin-2-yl-(quinazolin-4-yl)methanone derivatives represented by formula (I), pharmacologically acceptable salts thereof, and compositions containing such compounds are described. Methods for treating hyperproliferative disorders by administering the compounds are also described. 1,2,3,4-tetrahydroisoquinoline derivatives for making tetrahydroisoquinolin-2-yl-(quinazolin-4-yl)methanone compounds are also described.
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Page/Page column 30
(2014/09/29)
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- Efficient synthesis of 2-substituted phthalimides from phthalic acids in one step
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Efficient procedures for synthesizing 2-substituted phthalimide (isoindole-1,3-dione) analogues starting from phthalic acids have been developed by using experimental design. The phthalimide central fragment frequently appears in biologically active compounds, materials, catalysts, and fluorescent probes, and therefore the development of general, fast, and convenient synthetic methods to this scaffold under neutral, acidic, and basic conditions would be attractive. After an initial screening, the use of acetonitrile, acetic acid, or pyridine in combination with microwave heating proved most promising. Experimental design was applied to these conditions to optimize the time, temperature, and concentration. This strategy has successfully generated synthetic methods that have been used to synthesize a series of phthalimides from phthalic acids and various amines or anilines in excellent yields. The developed methods have proven to be general, fast, convenient, and economic, and thus are expected to have broad utility to efficiently construct novel compounds for future biological and chemical applications. Efficient procedures for synthesizing 2-substituted phthalimide (isoindole-1,3-dione) analogues starting from phthalic acids have been developed by using experimental design. The developed methods are fast, general, high-yielding, do not use additives, and are based on 1:1 molar ratios.
- Chorell, Erik,Chorell, Elin
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supporting information
p. 7512 - 7516
(2013/12/04)
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- NOVEL DERIVATIVES OF PHTHALIMIDE AS HISTONE DEACETYLASE INHIBITORS
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The invention relates to novel compounds of general formula (I), or one of the salts thereof, particularly one of the pharmaceutically acceptable salts thereof, or one of the corresponding solvates thereof. These compounds are inhibitors of the histone de
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Page/Page column 16
(2009/04/23)
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- N-(2-Amino-phenyl)-4-(heteroarylmethyl)-benzamides as new histone deacetylase inhibitors
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A variety of N-(2-amino-phenyl)-4-(heteroarylmethyl)-benzamides were designed and synthesized. These compounds were shown to inhibit recombinant human HDAC1 with IC50 values in the sub-micromolar range. In human cancer cells growing in culture these compounds induced hyperacetylation of histones, induced the expression of the tumor suppressor protein p21WAF1/Cip1, and inhibited cellular proliferation. Certain compounds of this class also showed in vivo activity in various human tumor xenograft models in mice.
- Vaisburg, Arkadii,Paquin, Isabelle,Bernstein, Naomy,Frechette, Sylvie,Gaudette, Frederic,Leit, Silvana,Moradei, Oscar,Raeppel, Stephane,Zhou, Nancy,Bouchain, Giliane,Woo, Soon Hyung,Jin, Zhiyun,Gillespie, Jeff,Wang, James,Fournel, Marielle,Yan, Pu Theresa,Trachy-Bourget, Marie-Claude,Robert, Marie-France,Lu, Aihua,Yuk, Jimmy,Rahil, Jubrail,MacLeod, A. Robert,Besterman, Jeffrey M.,Li, Zuomei,Delorme, Daniel
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p. 6729 - 6733
(2008/03/18)
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