Markus Gold

Synthesis and structure–affinity relationships of 1,3,5-alkylsubstituted cyclohexylamines binding at NMDA receptor PCP site

A series of 1,3,5-alkylsubstituted cyclohexylamines 2 were synthesized as ligands for the N-methyl-D-aspartate (NMDA) receptor phencyclidine (PCP) binding site. Pure diastereomers with defined configuration of amino group 2-ax and 2-eq were obtained. The optimal size of 1,3,5-substituents was determined for cyclohexylamines 2 with an equatorial amino group in the lowest energy conformation using Hansch analysis. According to the data, the lipophilic part of cyclohexylamines 2 does not discriminate between hydrophobic regions of the PCP binding site but rather recognizes this site as a whole lipophilic pocket.

Cyclic hydrazides: 1. Synthesis of 4-hydroxy-1-oxo-1,2-dihydropyridazino[4,5-b]quinolines

A series of dimethyl esters and cyclic hydrazides of quinoline-2,3-dicarboxylic acid has been synthesized with different substituents in the benzene ring.

Convenient Synthesis of 2,6-di-tert-Butyl-4-[5-(3-pyridyl)-4-oxapentyl]phenols and their thia-Analogues

A convenient large scale procedure for the synthesis of Nicanartine {2,6-di-tert-butyl-4-[5-(3-pyridyl)-4-oxapentyl]phenol}, an antiatherosclerotic compound has been developed, the synthetic route towards the thia-analogue as well as various branched-chain oxa- and thia-derivatives of the parent compound has also been investigated.

Oxidative Rearrangement of 3,5-Di-tert-butyl-4-hydroxybenzaldehyde Acetals

3,5-Di-tert-butyl-4-hydroxybenzaldehyde acetals rearrange to various esters when oxidized with potassium ferricyanide in alkaline medium.

Cyclic hydrazides. 2. Synthesis of substituted 4-hydroxy-1-oxo-1,2-dihydropyridazone[4,5-b]quinoline 5-oxides

Reaction of N-oxides of dimethyl quinoline-2,3-dicarboxylates with hydrazine and subsequent oxidation with peracetic acid has been given quinoline-2,3-dicarboxylic acid hydrazide 5-oxides, from which water solublequaternary ammonium salts can be prepared.