L-Proline compd. with (1S)-1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylmethyl)-4-fluorophenyl]-D-glucitol (1:1)

Product NameL-Proline compd. with (1S)-1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylmethyl)-4-fluorophenyl]-D-glucitol (1:1)
CAS951382-34-6
MFC21H21FO5S.C5H9NO2
MW519.58
EINECS
MOL File951382-34-6.mol

Chemical Properties

storage temp.	Store at -20°C
solubility	Soluble in DMSO
form	Solid
color	White to off-white

Usage And Synthesis

Uses

Ipragliflozin (L-Proline) is a highly potent and selective SGLT2 inhibitor with an IC50 of 2.8 nM; little and NO potency for SGLT1/3/4/5/6.

Synthesis

761423-87-4

147-85-3

L-Proline compd. with (1S)-1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylmethyl)-4-fluorophenyl]-D-glucitol (1:1)

951382-34-6

Synthesis of (2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol and L-proline as raw materials for the synthesis of (2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-( hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (S)-pyrrolidine-2-carboxylate was prepared in the following general procedure: in a dichloromethane solvent, 24.65 g (61.02 mmol)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol was added. pyran-3,4,5-triol and 7.02 g (61.02 mmol) of L-proline. The reaction mixture was heated to 35°C and stirred at this temperature for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and the crude product was collected by filtration. The crude product was purified by recrystallization from methanol to give 31.35 g of the target product, i.e., (2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophene-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (S)- pyrrolidine-2- carboxylate, with a purity of 99.8% and a yield of 99%.

in vivo

Ipragliflozin (L-Proline) shows good pharmacokinetic properties following oral dosing, and dose-dependently increases urinary glucose excretion, which lasts for over 12 h in normal mice ^[3]. Oral administration of ipragliflozin increases urinary glucose excretion in a dose-dependent manner, an effect which is significant at doses of 0.3 mg/kg or higher and lasts over 12 h^[4]. Single administration of ipragliflozin dose-dependently increases urinary glucose excretion, reduces blood glucose and plasma insulin levels, and improves glucose intolerance ^[5].

IC 50

SGLT2

References

[1] Imamura M, et al. Discovery of Ipragliflozin (ASP1941): a novel C-glucoside with benzothiophene structure as a potent and selective sodium glucose co-transporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes mellitus. Bioorg Med Chem. 2012 May 15;20(10):3263-79. DOI:10.1016/j.bmc.2012.03.051
[2] Suzuki M, et al. Tofogliflozin, a potent and highly specific sodium/glucose cotransporter 2 inhibitor, improves glycemic control in diabetic rats and mice. J Pharmacol Exp Ther. 2012 Jun;341(3):692-701. DOI:10.1124/jpet.112.191593
[3] Tahara A, et al. Pharmacological profile of ipragliflozin (ASP1941), a novel selective SGLT2 inhibitor, in vitro and in vivo. Naunyn Schmiedebergs Arch Pharmacol. 2012 Apr;385(4):423-36. DOI:10.1007/s00210-011-0713-z
[4] Tahara A, et al. Antidiabetic effects of SGLT2-selective inhibitor ipragliflozin in streptozotocin-nicotinamide-induced mildly diabetic mice. J Pharmacol Sci. 2012;120(1):36-44. DOI:10.1254/jphs.12089fp
[5] Tahara A, et al. Effects of SGLT2 selective inhibitor ipragliflozin on hyperglycemia, hyperlipidemia, hepatic steatosis, oxidative stress, inflammation, and obesity in type 2 diabetic mice. Eur J Pharmacol. 2013 Sep 5;715(1-3):246-55. DOI:10.1016/j.ejphar.2013.05.014

Preparation Products And Raw materials

L-Proline compd. with (1S)-1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylmethyl)-4-fluorophenyl]-D-glucitol (1:1) Supplier

L-Proline compd. with (1S)-1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylmethyl)-4-fluorophenyl]-D-glucitol (1:1) manufacturers

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