- Palladium(II) acetate as catalyst for the N-alkylation of aromatic amines, sulfonamides, and related nitrogenated compounds with alcohols by a hydrogen autotransfer process
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Palladium(II) acetate is a versatile, inexpensive, and simple catalyst for the selective N-monoalkylation of amino derivatives with poor nucleophilic character, such as aromatic and heteroaromatic amines as well as carboxamides, sulfonamides, and phosphazenes, using, in all cases, primary alcohols as the initial source of the electrophile, through a hydrogen autotransfer process. The regioselectivity of the benzothiazol-2-amine alkylation is contrary to that found using halogenated electrophiles.
- Martinez-Asencio, Ana,Yus, Miguel,Ramon, Diego J.
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experimental part
p. 3730 - 3740
(2011/12/21)
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- N-Alkylation of poor nucleophilic amine and sulfonamide derivatives with alcohols by a hydrogen autotransfer process catalyzed by copper(II) acetate
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Copper(II) acetate is a versatile, cheap, and simple catalyst for the selective N-monoalkylation of amino derivatives with poor nucleophilic character, such as aromatic and heteroaromatic amines as well as sulfonamides, using in all cases primary alcohols as initial source of the electrophiles, through a hydrogen autotransfer process. In the case of sulfonamides, the monoalkylation process followed by a naphthalene-catalyzed reductive deprotection gives primary amines, which is an indirect alternative to the direct monoalkylation of ammonia.
- Martínez-Asencio, Ana,Ramón, Diego J.,Yus, Miguel
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scheme or table
p. 325 - 327
(2010/03/04)
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- Identification of novel PPARα ligands by the structural modification of a PPARγ ligand
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To develop novel PPARα ligands, we designed and synthesized several 3-{3-[2-(nonylpyridin-2-ylamino)ethoxy]phenyl}propanoic acid derivatives. Compound 10, the meta isomer of a PPARγ agonist 1, has been identified as a PPARα ligand. The introduction of methyl and ethyl groups at the C-2 position of the propanoic acid of 10 further improved the PPARα-binding potency.
- Usui, Shinya,Fujieda, Hiroki,Suzuki, Takayoshi,Yoshida, Naoaki,Nakagawa, Hidehiko,Miyata, Naoki
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p. 3249 - 3254
(2007/10/03)
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- Design, synthesis, and biological activity of novel PPARγ ligands based on rosiglitazone and 15d-PGJ2
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To develop novel PPARγ ligands, we synthesized thirteen 3-{4-(2-aminoethoxy)phenyl}propanoic acid derivatives, which are designed based on the structures of rosiglitazone and 15d-PGJ2. Among these compounds, compound 9 was found to be as potent as rosiglitazone in a binding assay and a preadipocyte differentiation test. Molecular modeling suggested that the nonyl group of 9 interacted with hydrophobic amino acid residues constructing the hydrophobic region of PPARγ protein where the alkyl chain of 15d-PGJ2 is expected to be located.
- Usui, Shinya,Suzuki, Takayoshi,Hattori, Yoshifumi,Etoh, Kazuma,Fujieda, Hiroki,Nishizuka, Makoto,Imagawa, Masayoshi,Nakagawa, Hidehiko,Kohda, Kohfuku,Miyata, Naoki
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p. 1547 - 1551
(2007/10/03)
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