Synthesis and Biological Activity of Triacetonamine
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ynthesis and Biological Activity of Triacetonamine M. N. M. Yousifa,*, H. A. Solimana, M. M. Saidb, N. A. Hassana,c, and F. M. E. Abdel-Megeida a Photochemistry
Department, Chemical Industries Research Division, National Research Center, Dokki, Cairo, 12622 Egypt Chemistry Department, Faculty of Pharmacy and Drug Manufacturing, Pharous University in Alexandria, Alexandria, 12622 Egypt c Pharmaceutical Science Department, College of Pharmacy, Shaqra University, Riyadh, 11671 Saudi Arabia *e-mail: [email protected]
b Pharmaceutical
Received November 8, 2019; revised March 27, 2020; accepted March 28, 2020
Abstract—Sterically hindered amines such as triacetonamine and certain closely related analogs have been applied in medicine, pharmacology and industry. Various methods of synthesis of 2,2,6,6-tetramethylpiperidin-4-one (triacetonamine) derivatives start generally with acetone, phorone, piperidine N-oxides, piperidine alcohols, and 4-dimethylamine piperidine derivatives. Physical properties of triacetonamine including density, boiling point, flash point, and melting point have been determined. Reactions of triacetonamine derivatives with various organic reagents are also summarized. Triacetonamine derivatives react via three functional groups including carbonyl, methylenes adjacent to the carbonyl group, and NH. Some other miscellaneous reactions are presented. Conformation of triacetonamine is described. Theoretical models for the conformations of triacetonamine have been developed by quantum and molecular mechanics methods. Triacetonamine demonstrates different types of biological activities, such as antialzheimer, antifungal, antimicrobial, anti-HIV, anticancer, antioxidant, P38 kinase inhibitor, DNA labelling, antispasmodic, and psychotropic, and high ganglionic blocking. Keywords: 2,2,6,6-tetramethylpiperidin-4-one, triacetonamine, biological activity
DOI: 10.1134/S1070363220030202 presence of an acidic catalyst like calcium chloride in a 20% yield [5] (hereanafter, see supplemmantary materials). Co-catalysts bromine or iodine combined with acid halides of the type XCH2COX acted as synergists in the above process leading to 80–90% yield of the product [6]. b. From phorone and ammonia. Phorone 2 reacted with ammonia to give triacetonamine 1 via the nucleophilic addition of nitrogen to the olefinic bond [7]. c. From N-oxides. Triacetonamine was formed via reduction of cation 3 in the presence of NaOH in acetone media [8]. d. From alcohols. Photogenerated singlet oxygen was used in oxidation of alcohol 4 with formation of triacetonamine 1 under mild and facile conditions using the catalyst CoIIDPDME [9, 10]. e. From dimethylamine derivatives. Dimethylamine 5 was alkylated by methyl iodide. The following hydrolysis gave triacetonamine [11]. Chemical reactions. Reactions of the carbonyl group. The Beckman rearrangement of triacetonamine led to formation of 2,2,7,7-tetramethyl-5-homopiperazinone
Sterically hindered amines such as triacetonamine and their closely related analogs are characterized by a vari
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