- Synthesis and structure activity relationships of selected isomeric oxime O ethers as anticholinergic agents
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A series of isomeric (Z)- and (E)-oxime O-β-dimethylaminoethyl ether methylhalide derivatives was synthesized, and their (Z)- and (E)-assignments were made on the basis of chemical and spectral data. The respective (Z)- and (E)-isomers were evaluated as anticholinergic agents on the rat ileum. The antimuscarinic potencies of the respective (Z)- and (E)-isomers were compared to determine the effect upon potency of this type of geometric isomerism. Three general structure-activity relationships are discernible among the synthesized compounds: (a) among oxime O-ethers derived from aromatic aldehydes, the higher potency consistently resides in the isomer where the aryl substituent is (E) to the ammonium ether substituent; (b) among oxime O-ethers derived from diaryl ketones, the (Z)- and (E)-isomers are approximately equipotent; and (c) oxime O-ethers derived from diaryl ketones are the most potent of the synthesized compounds.
- Haney,Brown,Isaacson,Delgado
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- Palladium-Catalyzed Arylation of (Di)azinyl Aldoxime Ethers by Aryl Iodides: Stereoselective Synthesis of Unsymmetrical (E)-(Di)azinylaryl Ketoxime Ethers
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The first example of direct arylation of (di)azinyl aldoxime ethers by aryl iodides is reported. The reaction produces, in a single step, a variety of geometrically pure unsymmetrical (E)-(di)azinylaryl ketoxime ethers, a class of nitrogenated motifs that have found wide applications in medicinal and organic chemistry but are difficult to access using conventional procedure. The utility of the method is further illustrated in a formal synthesis of the Merck melanin-concentrating hormone, 1 receptor antagonist. Arylationship of convenience: Direct arylation of (di)azinyl aldoxime ethers by aryl iodides produces, in a single step, a variety of geometrically pure unsymmetrical (E)-(di)azinylaryl ketoxime ethers (see scheme), a class of nitrogenated motifs that have found wide application in medicinal and organic chemistry but are difficult to access by conventional procedures.
- Gou, Quan,Deng, Bin,Qin, Jun
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p. 12586 - 12591
(2015/09/01)
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- HIGH CHEMOSELECTIE SYNTHESIS OF CARBOXAMIDES BY USING SYN-PHENYLPYRIDYL-O-ACYL OXIMES(PPKO)
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Various carboxamides are prepared chemoselectively in good yields by using syn-phenylpyridyl ketoxime(PPKO) as functional leaving group.
- Miyasaka, Tadayo,Noguchi, Shunsaku
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p. 701 - 704
(2007/10/02)
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