Fushimi, Nobuhiko published the artcileDesign, synthesis, and structure-activity relationships of a series of 4-benzyl-5-isopropyl-1H-pyrazol-3-yl β-D-glycopyranosides substituted with novel hydrophilic groups as highly potent inhibitors of sodium glucose co-transporter 1 (SGLT1), Product Details of C19H34ClN, the publication is Bioorganic & Medicinal Chemistry (2013), 21(3), 748-765, database is CAplus and MEDLINE.
Sodium glucose co-transporter 1 (SGLT1) plays a dominant role in the absorption of glucose in the gut and is considered a promising target in the development of therapeutic options for postprandial hyperglycemia. Previously, we reported potent and selective SGLT1 inhibitors 1 and 2 showing efficacy in oral carbohydrate tolerance tests in diabetic rat models. In a pharmacokinetic (PK) study of glycoside I (R = OH), excessive systemic exposure to metabolites of I (R = OH) was observed, presumably due to the high permeability of its aglycon. To further improve SGLT1 inhibitory activity and reduce aglycon permeability, a series of 4-benzyl-5-isopropyl-1H-pyrazol-3-yl β-D-glycopyranoside derivatives, e.g. I (R = NH2), bearing novel hydrophilic substitution groups on the Ph ring were synthesized and their inhibitory activity toward SGLTs was evaluated. Optimized compound II showed an improved profile satisfying both higher activity and lower permeability of its aglycon. Moreover, the superior efficacy of II in various carbohydrate tolerance tests in diabetic rat models was confirmed compared with acarbose, an α-glucosidase inhibitor (α-GI) widely used in the clinic.
Bioorganic & Medicinal Chemistry published new progress about 23616-79-7. 23616-79-7 belongs to chlorides-buliding-blocks, auxiliary class Phase Transfer Catalyst, name is N-Benzyl-N,N-dibutylbutan-1-aminium chloride, and the molecular formula is C19H34ClN, Product Details of C19H34ClN.
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