Partly reduced biphenyls as central nervous system agents. 2. Cis- and trans-4-arylcyclohexylamines

Novel 4-(4-Aryl)cyclohexyl-1-(2-pyridyl)piperazines as Δ8−Δ7 Sterol Isomerase (Emopamil Binding Protein) Selective Ligands with Antiproliferative Activity

“…Consequently, novel 2-pyridinylpiperazine derivatives were designed in order to investigate the importance of methoxyl substituent on the phenyl moiety and the role of electronic and steric effects of other substituents (Me, Cl, F) in determining the binding affinities. Some 2,6-disubstituted-phenyl derivatives (32)(33)(34)(35) were prepared in order to hinder the free rotation of the phenyl ring linked to the cyclohexyl ring. The isomers of compound cis-19 for the methoxyl position and for cis/trans geometry were tested to complete a SAfiR study.…”

Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ0)

“…Mitsunobu reaction on the secondary alcohols using DEAD or DIAD did not provide the desired azides [42–43] nor did a one-pot Appel reaction/nucleophilic substitution/Staudinger reaction protocol involving a double inversion of configuration [44]. Mesylation of 26 and 27 lead to intermediates 28 and 29 [45], which were subsequently reacted with sodium azide inverting the stereochemistry as required [46]. A final transfer hydrogenation of 30 and 31 yielded the desired amines rapidly and with excellent yields [47].…”

Benzospirans bearing basic substitution. I. Spiro(cyclohexane-1,2'-indans)

“…We have reported earlier on the preparation and CNS activity of a series of derivatives of 4-arylcyclohex-3-enylamines (l)1 and 4-arylcyclohexylamines (2). 2 The observation that the ortho-substituted derivatives (la,b> 2a,b) in la, X = -CH, 2a, X = o-CH, b, X == o-OCH, b, X = o-OCH, each series showed considerable biological activity was considered of particular interest; interaction of the ortho substituent with the equatorial proton on the adjacent alicyclic ring make it likely that the preferred conformation of these molecules is one in which the two rings are in some skewed arrangement. We thus decided to prepare analogues of those compounds in which those rings would be actually locked orthogonal to each other.…”