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Synthesis of Important Chiral Building Blocks for Pharmaceuticals Using Lactobacillus and Rhodococcus Alcohol Dehydrogenases
Published in Peter Grunwald, Pharmaceutical Biocatalysis, 2019
Marion Rauter, Simon Krebs, Gotthard Kunze
Ketoesters as α- and β-ketoesters are reduced to α- and β-hydroxyesters, which are important intermediates for many complex substances. Those motifs can be found in a variety of natural products, such as statin side chains, prostaglandins or leukotrienes. Diketones are building blocks of many natural compounds such as pheromones or anti-tumor agents, whereas ketones with an aromatic side chain are used in a wide field of medicinal applications. Numerous substances contain halogenated side-chains of which α-halo ketones are from special interest. Their corresponding halohydrins are versatile intermediates for the synthesis of biologically active compounds as potent protease inhibitors employed against HIV. Fluorinated substances make approximately 20% of all available drugs. The application of heterocyclic chiral alcohols is as diverse as their structure. Some of them are used as intermediates for central nervous system modulators or as therapeutic agents against cocaine abuse (Cuetos et al., 2014).
Selective inhibition of carbonic anhydrase IX and XII by coumarin and psoralen derivatives
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2021
Rita Meleddu, Serenella Deplano, Elias Maccioni, Francesco Ortuso, Filippo Cottiglia, Daniela Secci, Alessia Onali, Erica Sanna, Andrea Angeli, Rossella Angius, Stefano Alcaro, Claudiu T. Supuran, Simona Distinto
A hot solution of methyl 2–(7-hydroxy-4-methyl-2-oxo-8-propyl-2H-chromen-3-yl)acetate (1 eq.) in dry acetone was treated with K2CO3 (2.5 eq.), stirred vigorously, and treated with the appropriate α-haloketone (1 eq.). The reaction mixture was heated to reflux and stirred for 1–5 h (course of the reaction monitored by TLC using ethyl acetate/n-hexane 5:1). When the reaction was completed, it was cooled at 0 °C and the solution acidified with HCl conc. The resulting precipitate was filtered off and crystallised if necessary.