84417-34-5Relevant articles and documents
Combination of Metal-Catalyzed Cycloisomerizations and Biocatalysis in Aqueous Media: Asymmetric Construction of Chiral Alcohols, Lactones, and γ-Hydroxy-Carbonyl Compounds
Rodríguez-álvarez, María J.,Ríos-Lombardía, Nicolás,Schumacher, S?ren,Pérez-Iglesias, David,Morís, Francisco,Cadierno, Victorio,García-álvarez, Joaquín,González-Sabín, Javier
, p. 7753 - 7759 (2017/11/10)
The combination of the metal-catalyzed cycloisomerization of alkynes containing a tethered nucleophile as substituent in aqueous media (followed by the spontaneous hydrolysis, hydroalkoxylation, or aminolysis of the transiently formed five-membered heterocycles) with the subsequent enantioselective ketone bioreduction (mediated by KREDs) has been achieved. The overall transformations, which formally involve a three-step one-pot reaction, provide a variety of enantiopure valuable molecules (e.g., 1,4-diols, lactones, and γ-hydroxy-carbonyl compounds (carboxylic acids, esters, and amides)) with high conversions and enantioselectivities and under mild reaction conditions, disclosing the concept of integrated metal-catalyzed cycloisomerizations of alkynes and enzymatic catalysis in water.
Conjugates of Catecholamines. 1. N-Alkyl-Functionalized Carboxylic Acid Congeners and Amides Related to Isoproterenol
Jacobson, Kenneth A.,Marr-Leisy, Debra,Rosenkranz, Roberto P.,Verlander, Michael S.,Melmon, Kenneth L.,Goodman, Murray
, p. 492 - 499 (2007/10/02)
A series of functionalized catecholamines (congeners) has been synthesized in which, formalistically, N-isopropyl group of isoproterenol has been extended by a linear alkyl chain of varying length, terminated by a carboxy group or a substituted amide.The compounds were prepared generally via the reductive amination of norepinephrine with a keto acid or a preformed keto amide.An alternate synthesis of the model amide derivatives, involving activation of the carboxylic acid congeners and coupling with amines, was complicated in the case of short-chain derivatives by facile cyclization to lactams.In vitro evaluation of these compounds as potential β-adrenergic agonists has shown that, while the carboxylic acid congeners have relatively low potencies, the model amide derivatives have potencies that are highly dependent on both the length of the alkyl chain and also the nature of the substituent on the amide.In general, aromatic amides are the most potent, although the nature and position of substituents on the aromatic group dramatically influences their potency.The implications of these studies, in terms of general β-adrenergic drug design and also the attachment of the carboxylic acid congeners to carries, are discussed
