37155-50-3Relevant articles and documents
Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia
Liu, Caiping,Han, Jingxuan,Marcelina, Olivia,Nugrahaningrum, Dyah Ari,Huang, Song,Zou, Meijuan,Wang, Guixue,Miyagishi, Makoto,He, Yun,Wu, Shourong,Kasim, Vivi
supporting information, p. 135 - 162 (2022/01/14)
Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-molecule drugs capable of inducing it at the clinical level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and druggable angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and nondiabetic HLI mice. Together, this study offers a novel, promising small-molecule-based therapeutic strategy for treating HLI.
An efficient and practical preparation of a potent low-affinity na+-dependent glucose cotransporter (SGLT2) inhibitor, sergliflozin etabonate
Kobayashi, Masahiro,Isawa, Hidetoshi,Sonehara, Junichi,Kubota, Minoru
, p. 1599 - 1613 (2016/10/12)
The development of an efficient and practical process for the preparation of Sergliflozin etabonate (1), a prodrug of a novel selective low-affinity Na+-dependent glucose cotransporter (SGLT2) inhibitor, Sergliflozin (2), is described. Its development required a suitable process for large-scale manufacturing. We established a chromatography-free approach for 2-[(4-methoxyphenyl)methyl]phenol (5), the efficient O-glycosylation of 5 with penta-O-acetyl-β-D-glucopyranose (7) without using a trichloroacetimidate intermediate (9), and efficient reaction conditions to introduce an ethoxycarbonyl group onto the primary alcohol of 2 with high selectivity. This process provided 1 with a 45% overall yield from anisole (10).
Design, syntheses, and SAR studies of carbocyclic analogues of sergliflozin as potent sodium-dependent glucose cotransporter 2 inhibitors
Shing, Tony K. M.,Ng, Wai-Lung,Chan, Judy Y.-W.,Lau, Clara B.-S.
supporting information, p. 8401 - 8405 (2013/09/02)
Combating diabetes: A small-molecule carbohydrate mimic, pseudo-sergliflozin, was synthesized effectively by a regio- and stereoselective allylic substitution reaction. It was found to be a potent and selective inhibitor of a transporter protein - sodium-dependent glucose cotransporter 2 (SGLT2) - which is responsible for glucose reabsorption in the human body. It could be a lead compound for further development into an antidiabetic agent. Copyright