Piperazinyl piperidines

Tagat, J.R., Steensma, R.W., McCombie, S.W. et al. (2001) Piperazine-based CCR5 antagonists as HIV-1 inhibitors. II. Discovery of 1 - [(2,4-dimethyl-3-pyridinyl)carbonyl]-4- methyl-4- [3 (S)-methyl-4- [ 1 (5)- [4-(trifluoro- methyl)phenyl]ethyl]-l-piperazinyl]-piperidine Nl-oxide (sch-350634), an orally bioavailable, potent CCR5 antagonist. Journal of Medicinal Chemistry, 44 (21), 3343-3346. 

Piperazinyl-Piperidines. Schering-Plough has filed many patents describing a piper-azinyl-piperidine scaffold, a very general structure of which is shown as 36. It is of interest to point out that a number of compounds within this class has subnanomolar affinities and as such this class appears to be one of the most active CXCR3 series known. For example, 37-39 all have Ki = 0.2nM ( [.cxCLlO) [91-93]. 

Deprotonation of the 9-azabicyclo 3.3.11nonan-3-one derivative 1 with chiral lithium amides in tetrahdyrofuran at low temperatures in the presence of chlorotrimethylsilane (internal quench) gives the trimethylsilyl enol ether (lS,5/ )-2 in high yield with high enantiomeric excess. The absolute configuration and enantiomeric excess of 2 are based on chemical correlation and HPLC on a chiral Daicel OJ column, respectively38. The 2,2-dimethylpropyl- and 4-methyl-l-piperazinyl- substituted lithium amide is, as noted in other cases, superior. The bicyclic trimethylsilyl enol ether 2 serves as intermediate in the synthesis of piperidine alkaloids. 

Piperazinyl) ethanol 2-Piperazin-1-yl-ethanol. See N-Hydroxyethylpiperazine 2-Piperazin-1-yl ethylamine. See Am i noethyl pi perazi ne Piper cubeba Piper cubeba fruit oil Piper cubeba oil. See Cubeb (Piper cubeba) oil Piperidic acid. See Aminobutyric acid Piperidine... 

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