Malonic acid receptors with decarboxylative activity

Troger's Base Molecular Scaffolds in Dicarboxylic Acid Recognition

“…The most striking feature of the recognition of dicarboxylic acids is their selective binding by synthetic receptors. [3][4][5][6][7] The precise selectivity between two purely aliphatic dicarboxylic acids (close homologues) is more difficult. This happens owing to the fact that the bond rotation in an open chain can occur freely and the two carboxyl ends in the extended chain compromise to come closer for hydrogen-bonding contacts with the receptor binding groups if they demand so.…”

“…In this context, selective binding of glutaric acid has been reported by a resorcinolaldehyde (dodecyl aldehyde and pentyl aldehyde) cyclotetramer 6 and of dibutylmalonic acid by a receptor having a benzophenone spacer between the two urea or phosphonamide type binding moieties in the cavity for the carboxylic acid. 7 In search for a conformationally and geometrically well-defined linker to hold the hydrogen-bonding groups, we report here Troger's base as a unique structural feature for the construction of novel molecular receptors for dicarboxylic acid recognition studies. The chiral complexation of (+)-camphoric acid with the (()-Troger's base receptors is also reported.…”

“…The design and synthesis of model receptors to recognize substrates of biochemical significance utilizing these weak forces to mimic biological events are of keen interest in molecular recognition research. , During the last decade, a lot of synthetic receptors for dicarboxylic acids have been designed and synthesized on the basis of the use of a relatively small number of interacting H-bonding groups. The most striking feature of the recognition of dicarboxylic acids is their selective binding by synthetic receptors. − The precise selectivity between two purely aliphatic dicarboxylic acids (close homologues) is more difficult. This happens owing to the fact that the bond rotation in an open chain can occur freely and the two carboxyl ends in the extended chain compromise to come closer for hydrogen-bonding contacts with the receptor binding groups if they demand so.…”

Synthesis of 2-(aminophenyl)adenine derivatives: a simple protocol using the classical iron powder/acetic acid reduction methodology

“…), combined with aqueous hydrochloric acid, in ethanol, at 65 o C, for 14.5h, following an experimental procedure previously described in the literature. 8 The product 4a was isolated but in very low yield ( Table 2, entry 3). Iron powder was then considered for the reduction.…”

8-Benzamidochromen-4-one-2-carboxylic Acids: Potent and Selective Agonists for the Orphan G Protein-Coupled Receptor GPR35

“…13 Ethyl 8-amino-4-oxo-4H-chromene-2-carboxylate (17). 4 The compound was synthesized using 12 (2.21 g, 8.4 mmol) and was isolated as a yellow solid (1.74 g, 89% yield). 1 H NMR: δ 1.35 (t, J = 7.1 Hz, 3H, CH 3 ), 4.39 (q, J = 7.1 Hz, 2H, CH 2 ), 5.50 (br, 2H, NH 2 ), 6.87 (s, 1H, 3-H), 7.11 (dd, J = 7.5 Hz, J = 1.9 Hz, 1H, 7-H), 7.16-7.22 (m, 2H, 5-H, 6-H).…”