mannich-bases and acetophenone

A review of selected literature data related to intramolecular hydrogen bonding in

Topics: Acetophenones; Amides; Hydrogen Bonding; Ketones; Magnetic Resonance Spectroscopy; Mannich Bases; Protons; Pyridoxal; Quantum Theory; Salicylamides; Schiff Bases

Here we report that, unlike other ketones, 1-indanone and acetophenone derived enolates undergo Mannich-type addition reactions with N-tert-butanesulfinyl ketimines with excellent yields (up to 98%) and diastereoselectivity (>99/1). The resulting compounds represent a new type of biologically relevant β-aminoketone derivative bearing quaternary stereogenic carbon, which could be further converted into the corresponding β-amino ketones and β-amino alcohols, possessing three consecutive stereogenic centres.

Topics: Acetophenones; Carbon; Imines; Indans; Mannich Bases; Molecular Conformation; Nitriles; Proton Magnetic Resonance Spectroscopy; Stereoisomerism

A highly enantioselective three-component reaction of a diazoacetophenone, an alcohol, and an imine catalyzed cooperatively by Rh(2)(OAc)(4) and BINOL-derived chiral phosphoric acid has been developed for the synthesis of chiral β-amino-α-hydroxyl ketones in good yield with excellent diastereo and enantio selectivity.

Topics: Acetophenones; Alcohols; Azo Compounds; Catalysis; Imines; Mannich Bases; Naphthols; Phosphoric Acids; Rhodium; Stereoisomerism

Jurkat cells were exposed to representative acetophenone-derived mono Mannich bases 2 and 3 and also cyclic Mannich base C1 in culture conditions to see the alterations in the most abundant cellular thiol, glutathione and also some of the enzymes in its metabolic pathway. Jurkat cells were exposed to the compounds for 24 h in cell culture medium with fetal bovine serum (1%) at 37 degrees C under a humidified atmosphere of 95% air and 5% CO2. Mannich bases generally increased total glutathione level (123-151% of control). Glutathione S-transferase (GST) activity also increased (150-363% of control), while glutathione disulfide reductase (GRD) activity was not affected. The increase in cellular glutathione level may possibly result from de novo glutathione synthesis. The consumption of the glutathione due to alkylation by Mannich bases might have stimulated the enzymes in the gamma-glutamyl cycle in our experimental design, where the cells had nutrients and time to react with their feedback mechanisms. A remarkable increase in GST activity might be a compensatory up-regulation to detoxify Mannich bases by conjugating them with cellular thiols.

Topics: Acetophenones; Dose-Response Relationship, Drug; Glutathione; Glutathione Reductase; Glutathione Transferase; Humans; Jurkat Cells; Mannich Bases; NADH, NADPH Oxidoreductases; Thioredoxin-Disulfide Reductase