Single Hydroxy Group Research Articles

Synthesis, binding properties and self-functionalization of a steroid-capped porphyrin

A porphyrin capped with a steroidal superstructure bearing convergent hydroxy groups has been synthesized and shown to bind a variety of functionalized amines via a combination of metal–amine and hydrogen-bonding interactions; the metal–ligand interaction was used to catalyse and control selective acylation of a single hydroxy group in the cap.

Aporphines as antagonists of dopamine D-1 receptors

The aporphine alkaloids are a class of compounds known to possess activity at both D-1 and D-2 dopamine receptors. (R)-Apomorphine and (S)-bulbocapnine are examples of compounds which have agonist and antagonist activity, respectively, at D-1 receptors. A series of optically pure aporphines was synthesized and their activity at D-1 and D-2 dopamine receptors was studied. The (R)-aporphines uniformly had greater affinity for both D-1 and D-2 receptors than their S antipodes. Dihydroxy compound (R)-apomorphine, in accord with previous studies, was found to be a D-1 agonist. Aporphines possessing a single hydroxy group at C-11 are antagonists at the D-1 receptor. The corresponding methoxy compounds are virtually inactive at dopamine receptors. The most potent compounds, (R)-11-hydroxyaporphine (R-14) and (R)-10-bromo-11-hydroxyaporphine (R-26), are more potent than bulbocapnine as D-1 antagonists but are not as selective. A model for binding of aporphines to the D-1 receptor was formulated in which binding interactions between the receptor and the basic nitrogen and the C-11 hydroxy group of the aporphine are required for high-affinity binding to the receptor. The absolute configuration at C-6a determines the orientation of the N-6 lone pair and binding is optimal for the 6aR series. The agonist or antagonist activity of an aporphine is determined by the presence or absence, respectively, of a hydroxy group at C-10. A hydrophobic binding site may be present and may account for the high antagonist activity of (S)-bulbocapnine.

ChemInform Abstract: Controlled Oxidative Coupling of Glycals: A New Strategy for the Rapid Assembly of Oligosaccharides.

AbstractControlled oxidative coupling of various glucal triethers such as (I) with glucals containing a single hydroxy group either at C‐4 or C‐3 and acyloxy groups at the two other positions such as (II) yields α‐linked disaccharides such as (III).

Binding of phenols to aluminum oxide surfaces. 1. Phenols with a single hydroxy group

Binding of phenols to aluminum oxide surfaces. 1. Phenols with a single hydroxy group