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

storage temp. 

Store at -20°C

solubility 

Soluble in DMSO

form 

Solid

color 

White to off-white

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

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

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

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)Related Product Information

• Benzo[b]thiophene, 2-[(5-broMo-2-fluorophenyl)Methyl]-
• Benzo[b]thiophene-2-Methanol, α-(5-broMo-2-fluorophenyl)-
• Methyl 1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]-
• Ipragliflozin