Duvoglustat Free Base

• CAS: 19130-96-2
• Catalog Number: ACM19130962-1
• Category: Inhibitors
• Molecular Weight: 163.17
• Molecular Formula: C6H13NO4
• Description: Duvoglustat Free Base is an alpha-glucosidase inhibitor with antiviral action. Derivatives of deoxynojirimycin may have anti-HIV activity.
• Synonyms: Duvoglustat Free Base; BAY-h5595; BAY-h-5595; BAY-h 5595; 1-deoxynojirimycin
• IUPAC Name: (2R,3R,4R,5S)-2-(Hydroxymethyl)piperidine-3,4,5-triol
• Canonical SMILES: O[C@@H]1[C@@H](CO)NC[C@H](O)[C@H]1O
• InChI: InChI=1S/C6H13NO4/c8-2-3-5(10)6(11)4(9)1-7-3/h3-11H,1-2H2/t3-,4+,5-,6-/m1/s1
• InChI Key: LXBIFEVIBLOUGU-JGWLITMVSA-N
• Solubility: To be determined
• Appearance: Solid powder
• Shelf Life: >2 years if stored properly
• Storage: Dry, dark and at 0-4 °C for short term (days to weeks) or -20 °C for long term (months to years).
• Alternative CAS: 19130-96-2 (free base); 73285-50-4 (HCl)
• Biological Target: 1-Deoxynojirimycin (Duvoglustat) is an active α-glucosidase inhibitor. 1-Deoxynojirimycin suppresses postprandial blood glucose and is widely used for diabetes mellitus.
• Drug Formulation: To be determined
• Elemental Analysis: C, 44.17; H, 8.03; N, 8.58; O, 39.22
• Exact Mass: 163.0845
• HS Tariff Code: 2934.99.9001
• In Vitro Activity: The primary mammary epithelial cells were seeded into a 6-well plate at the density of 3 × 105/cm2, and the wells were added with DNEM/F12 medium containing 6 μM DNJ. DNJ treatment supplied pAD-LEF-1-mediated LEF-1 overexpression vector that resulted in LEF-1 overexpression that could synergistically display a remarkable effect on increasing the primary mammary epithelial cell density (Figures 2(a) and 2(c)). In addition, DNJ displayed a similar function in alleviating the growth suppression of epithelial cell and the decrease of LEF-1 mRNA level resulting from lentiviral-mediated LEF-1 knockdown. In conclusion, DNJ could improve breast epithelial cell growth through upregulating LEF-1 expression, which supplied a new means in studying mammary gland growth and development.; Reference: Biomed Res Int. 2018 Feb 19;2018:7809512. https://pubmed.ncbi.nlm.nih.gov/29670907/
• In Vivo Activity: The present study investigated the effect of 1-Deoxynojirimycin (DNJ) on liver injury and hepatic glucose metabolism in db/db mice. Mice were divided into five groups: normal control, db/db control, DNJ-20 (DNJ 20 mg·kg(-1)·day(-1)), DNJ-40 (DNJ 40 mg·kg(1)·day(-1)) and DNJ-80 (DNJ 80 mg·kg(-1)·day(-1)). DNJ treatment remarkably reduced serum levels of TG (triglyceride), TC (total cholesterol) and LDL-C (low-density lipoprotein cholesterol ) in a dose-dependent manner. Liver lipid content and lipid droplet size were significantly attenuated by DNJ treatment in a dose-dependent manner. DNJ treatment also notably decreased the levels of TNFα, IL-1, and IL-6 in liver tissue in a dose-dependent manner when compared with the db/db control group. Moreover, DNJ increased the phosphorylation of phosphatidylinositol 3 kinase (PI3K) on p85, protein kinase B (PKB) on Ser473, glycogen synthase kinase 3β (GSK-3β) on Ser9, and inhibited phosphorylation of glycogen synthase (GS) on Ser645 in liver tissue of db/db mice. These results demonstrate that DNJ can increase hepatic insulin sensitivity via strengthening of the insulin-stimulated PKB/GSK-3β signal pathway and by modulating glucose metabolic enzymes in db/db mice.; Reference: Molecules. 2016 Feb 27;21(3):279. https://pubmed.ncbi.nlm.nih.gov/26927057/
• Shipping: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
• Stock Solution Storage: 0-4 °C for short term (days to weeks), or -20 °C for long term (months).

Synthetic Use

Upstream Synthesis Route 1

• 132198-14-2

• 19130-96-2

Reference: [1]Journal of Organic Chemistry,1994,vol. 59,p. 3175 - 3185
[2]Tetrahedron Letters,1990,p. 6777
[3]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1255 - 1260

Downstream Synthesis Route 1

• 50-00-0
• 19130-96-2

• 69567-10-8

Reference: [1]Journal of the American Chemical Society,1991,vol. 113,p. 6187 - 6196
[2]Agricultural and Biological Chemistry,1988,vol. 52,p. 121 - 128
[3]Journal of Medicinal Chemistry,1995,vol. 38,p. 2349 - 2356

Downstream Synthesis Route 2

• 19130-96-2
• 100-39-0

• 72458-46-9

Reference: [1]Hines, Jennifer V.; Chang, Heesun; Gerdeman, Melinda S.; Warn, Dana E.
[Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 9, p. 1255 - 1260]
[2]Boeshagen; Heiker; Schueller
[Carbohydrate research, 1987, vol. 164, p. 141 - 148]
[3]Jockusch; Talbot; Asano; Fleet; Simons
[Physical Chemistry Chemical Physics, 2004, vol. 6, # 23, p. 5283 - 5287]

* For details of the synthesis route, please refer to the original source to ensure accuracy.