- N-Heteroarylmethyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylic acid a novel scaffold for the design of uncompetitive α-glucosidase inhibitors
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Abstract The enzyme α-glucosidase has attracted interest owing to its involvement in the digestive process of carbohydrate, its role in intracellular glycoprotein trafficking, tumorigenesis and viral infection. In this study, several members of a new family of N-heteroarylmethyl substituted azasugars were synthesized and evaluated as α-glucosidase inhibitors. We systematically investigated the effect of different N-substituents as well as the role of hydroxyl and carboxylate moieties on the piperidine ring. The compounds N-heteroarylmethyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylic acid emerged as potent α-glucosidase inhibitors. Unlike Acarbose and other clinically relevant α-glucosidase inhibitors, these compounds act through a reversible uncompetitive mechanism of inhibition which make them attractive candidates for drug development.
- Long, Sha,Stefani, Francesca Romana,Biondi, Stefano,Ghiselli, Giancarlo,Panunzio, Mauro
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p. 5811 - 5822
(2013/09/12)
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- Convenient formal synthesis of (±)-paroxetine
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A formal total synthesis of antidepressant (±)-paroxetine employing a solvent-free Heck reaction is disclosed. Copyright Taylor & Francis Group, LLC.
- Chavan, Subhash P.,Khobragade, Dushant A.,Pathak, Ashok B.,Kalkote, Uttam R.
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p. 3143 - 3149
(2008/02/13)
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- An approach to the tricyclic core of madangamines based upon a biogenetic scheme
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(Chemical Equation Presented) A short synthesis of intermediates possessing the tricyclic core of natural madangamines, bioactive alkaloids found in marine sponges, is described. The key reaction entails the condensation of the sodium salt of diethylaceto
- Han, Min Tong,Martin, Marie-Therese,Chiaroni, Angele,Benechie, Michel,Marazano, Christian
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p. 2437 - 2440
(2007/10/03)
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