Notes-Derivatives of 2-Amino-1,3-propanediol

Schipper, Edgar; Chinery, Edwin; Nichols, Joseph

doi:10.1021/jo01068a626

Cited by 9 publications

(1 citation statement)

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“…Reduction of the nitro group should give a primary amine 14 , which upon N ‐alkylation should be a central building block for the preparation of a library of aminoacetals. To our surprise, first attempts to reduce the nitro group by transfer hydrogenation with ammonium formate, as previously described for related substrates with Raney nickel or palladium catalysts , failed completely. Finally, hydrogenation with Raney nickel and hydrazine as the hydrogen transfer agent gave the desired primary amine 14 in 25% yield (Scheme ).…”

Section: Resultsmentioning

confidence: 93%

Steroidomimetic Aminomethyl Spiroacetals as Novel Inhibitors of the Enzyme Δ8,7‐Sterol Isomerase in Cholesterol Biosynthesis

Krojer

Müller

Bracher

2013

Archiv der Pharmazie

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Grundmann's ketone is converted to a spiroacetal containing a 5-hydroxymethyl-5-nitro-1,3-dioxane moiety whose hydroxymethyl group can be esterified or directly substituted with primary and secondary amines. Among the resulting aminomethyl spiroacetals, several ones bearing diamino residues were found to be inhibitors of the enzyme Δ8,7-isomerase in cholesterol biosynthesis. The complex bicyclic building block derived from Grundmann's ketone could be replaced by a properly substituted tetraline scaffold, without noteworthy loss in activity. This opens the opportunity to perform further structural modifications for the design of new steroidomimetic inhibitors of human Δ8,7-isomerase.

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Section: Resultsmentioning

confidence: 93%