Stereochemistry of 2,6-Dipyridine Substituted N-Benzyl-4-piperidone Mono- and Dicarboxylates and of the Corresponding Reduction Products

Holzgrabe, Ulrike; Piening, B.; Hesse, K.-F.; Höltje, Hans‐Dieter; Worch, M.

doi:10.1515/znb-1989-0512

Cited by 4 publications

(1 citation statement)

References 9 publications

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“…The obtained residue was covered with a small amount of methanol, and the product crystallized at 4 °C. The analytical and spectroscopic data of 19 – 24 are in accordance with refs – .…”

Section: Methodssupporting

confidence: 76%

In Search of Novel Agents for Therapy of Tropical Diseases and Human Immunodeficiency Virus

et al. 2007

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Malaria, sleeping sickness, Chagas' disease, Aleppo boil, and AIDS are among the tropical diseases causing millions of infections and cases of deaths per year because only inefficient chemotherapy is available. Since the targeting of the enzymes of the polyamine pathway may provide novel therapy options, we aimed to inhibit the deoxyhypusine hydroxylase, which is an important step in the biosynthesis of the eukaryotic initiation factor 5A. In order to identify new lead compounds, piperidines were produced and biologically evaluated. The 3,5-diethyl piperidone-3,5-dicarboxylates 11 and 13 substituted with 4-nitrophenyl rings in the 2 and 6 positions were found to be active against Trypanosoma brucei brucei and Plasmodium falciparum combined with low cytotoxicity against macrophages. The corresponding monocarboxylates are only highly active against the T. brucei brucei. The piperidine oximether 53 demonstrated the highest plasmodicidal activity. Moreover, compounds 11 and 53 were also able to inhibit replication of HIV-1.

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Section: Methodssupporting

confidence: 76%

In Search of Novel Agents for Therapy of Tropical Diseases and Human Immunodeficiency Virus

et al. 2007

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ChemInform Abstract: Stereochemistry of 2,6‐Dipyridine Substituted N‐Benzyl‐4‐piperidone Mono‐ and Dicarboxylates and of the Corresponding Reduction Products.

Holzgrabe¹,

Piening²,

Hesse³

et al. 1989

ChemInform

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Synthesis, structural, and biochemical study of a series of methyl 2,6‐diaryl‐1‐methyl‐4‐oxopiperidine‐3,5‐dicarboxylates and a series of methyl 2,4‐diaryl‐3,7‐dimethyl‐9‐oxo‐3,7‐diazabicyclo[3.3.1]nonane‐1,5‐dicarboxylates

Fernández

Casares

Galvez

et al. 1992

Journal of Heterocyclic Chem

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A series of methyl‐2,6‐diaryl‐1‐methyl‐4‐oxopiperidine‐3,5‐dicarboxylates Ia‐c and 2,4‐diaryl‐3,7‐dimethyl‐1,5‐dimethoxycarbonyl‐9‐bispidinones IIa‐c have been synthesized and studied by ir, 1H and 13C nmr spectroscopy and the crystal structure of methyl 2,4‐diphenyl‐3,7‐dimethyl‐9‐oxo‐3,7‐diazabicyclo[3,3.1]nonane‐1,5‐dicarboxylate (IIa) has been determined by X‐ray diffraction. The enolic form of compound Ia (I'a) was also studied.

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Stereochemistry of 2,6-Dipyridine Substituted N-Benzyl-4-piperidone Mono- and Dicarboxylates and of the Corresponding Reduction Products

Cited by 4 publications

References 9 publications

In Search of Novel Agents for Therapy of Tropical Diseases and Human Immunodeficiency Virus

In Search of Novel Agents for Therapy of Tropical Diseases and Human Immunodeficiency Virus

ChemInform Abstract: Stereochemistry of 2,6‐Dipyridine Substituted N‐Benzyl‐4‐piperidone Mono‐ and Dicarboxylates and of the Corresponding Reduction Products.

Synthesis, structural, and biochemical study of a series of methyl 2,6‐diaryl‐1‐methyl‐4‐oxopiperidine‐3,5‐dicarboxylates and a series of methyl 2,4‐diaryl‐3,7‐dimethyl‐9‐oxo‐3,7‐diazabicyclo[3.3.1]nonane‐1,5‐dicarboxylates

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