Synthese und lokalanästhetische Wirkung von N‐Piperidino‐methyl‐4‐alkoxybenzamiden

Schönenberger, Helmut; Bindl, L.; Petter, A.; Zwez, W.

doi:10.1002/ardp.19703031003

Cited by 6 publications

(3 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Support for the proposed elimination reaction comes from the work of Sch6nenberger et al [13], who showed that aromatic /3-amino ketones undergo spontaneous elimination of the amine moiety in neutral solution, with formation of the acrylophenone. A wide range of biological activities was exhibited by the compounds studied and the authors proposed a mechanism of action similar to the one above.…”

Section: Discussionmentioning

confidence: 97%

Analogs of ceramide that inhibit glucocerebroside synthetase in mouse brain

Vunnam

Radin

1980

Chemistry and Physics of Lipids

123

View full text Add to dashboard Cite

In a search for potent inhibitors of glucocerebroside biosynthesis, we synthesized aromatic analogs of the enzyme's substrate, ceramide, many of which have not previously been described in the literature. Mouse brain and spleen, rat brain, and human placenta and spleen were all found to be susceptible to inhibition by a variety of compounds, although to differing extents. The most potent inhibitor was 2-decanoylamino-3-morpholino-1-phenylpropanol. The dehydro version of this compound (2-decanoylamino-3-morpholinopropiophenone) was less effective but it produced inactivation of the enzyme, probably by covalent reaction with the enzyme's active site. Examination of the various effects seen leads us to suggest that the active region of the enzyme contains four recognitional sites: an anionic moiety that may bind the glucose in activated form, an oxygen-binding region oriented toward the third carbon atom of ceramide, a narrow region that binds the alkyl chain of the fatty acid moiety, and a less narrow region that binds the hydrocarbon chain of the sphingoid base moiety.

show abstract

Section: Discussionmentioning

confidence: 97%

Analogs of ceramide that inhibit glucocerebroside synthetase in mouse brain

Vunnam

Radin

1980

Chemistry and Physics of Lipids

123

View full text Add to dashboard Cite

show abstract

“…Mitochondrial activity-effect of Mannich bases and related compounds, yeast 0 Blood platelet aggregation-effect of Mannich bases and related compounds, rats 0 Coagulation, hlood-effect of Mannich bases and related compounds, rats Structure-activity relationships-effect of Mannich bases and related compounds on mitochondrial function in yeast, human epidermoid carcinoma cultures, hlood platelet aggregation and hlood clotting, rats Mannich bases have a wide range of biological activity including antineoplastic properties (1,2), antimicrobial effects (3)(4)(5), analgesic activity (6), local anesthetic properties (7,8), and psychotropic effects (9). To pursue a continuing interest in Mannich reactions (10)(11)(12) and cu,/%unsaturated ketones (13,14), several properties of a simple Mannich base, 5-dimethylamino-1 -phenyl-1 -penten-3-one (Ia ), derived aThe figures, in micrograms per milliliter, in the KB cell culture screen indicate the dose inhibiting 50% growth of human epidermoid carcinoma of the nasopharynx in Eagle's medium.…”

mentioning

confidence: 99%

“…I n uitro release of the drug from such silicone-type vaginal devices followed either of two kinetic mechanisms, matrix controlled or partition controlled, depending on whether the diffusion across the polymer phase or the partitioning across the polymer-solution interface was the ratelimiting step (2). I n uitro release of the drug from such silicone-type vaginal devices followed either of two kinetic mechanisms, matrix controlled or partition controlled, depending on whether the diffusion across the polymer phase or the partitioning across the polymer-solution interface was the ratelimiting step (2).…”

mentioning

confidence: 99%