ChemicalBook Product Catalog Biochemical Engineering Biochemical Reagents Agonist Inhibitors ZLN005

ZLN005

Product NameZLN005
CAS49671-76-3
MFC17H18N2
MW250.34
EINECS
MOL File49671-76-3.mol

Chemical Properties

Melting point	257-258℃
Boiling point	415.3±38.0 °C(Predicted)
Density	1.102±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Store in freezer, under -20°C
solubility	DMSO: soluble10mg/mL, clear
pka	11.52±0.10(Predicted)
form	powder
color	white to beige
InChI	1S/C17H18N2/c1-17(2,3)13-10-8-12(9-11-13)16-18-14-6-4-5-7-15(14)19-16/h4-11H,1-3H3,(H,18,19)
InChIKey	LQUNNCQSFFKSSK-UHFFFAOYSA-N
SMILES	[nH]1c2c(nc1c3ccc(cc3)C(C)(C)C)cccc2

Safety Information

Hazard Codes	Xn
Risk Statements	22-36
Safety Statements	26
WGK Germany	3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

Peroxisome proliferator-activated receptor-γ coactivator-1α (PGC-1α) is a tissue-specific and inducible transcriptional coactivator for several nuclear receptors and plays a key role in energy metabolism, hepatic gluconeogenesis, and cholesterol homoeostasis. ZLN005 is a small molecule that stimulates the expression of PGC-1α and downstream genes in skeletal muscle cells, improving glucose utilization and fatty acid oxidation at a concentration of 20 μM. Chronic administration of 15 mg/kg/day ZLN005 to diabetic db/db mice increased PGC-1α and downstream gene transcription in skeletal muscle, increasing fat oxidation and improving glucose tolerance, pyruvate tolerance, and insulin sensitivity.

Uses

ZLN005 increaces PGC-1α and downstream gene transcription in skeletal muscles and increases fat oxidation and improved the glucose tolerance, pyruvate tolerance, and insulin sensitivity of diabetic db/db mice.

Synthesis

877-65-6

95-54-5

49671-76-3

The reaction was carried out in a magnetically stirred round-bottomed flask equipped with a condenser and placed in a temperature-controlled oil bath. O-phenylenediamine (2 mmol) was added to 4-tert-butylbenzyl alcohol (3 mmol) and the reaction mixture was stirred at 135 °C in an open (air) atmosphere. The reaction was monitored by TLC and after complete disappearance of the o-phenylenediamine or after the reaction had reached a predetermined time, the reaction mixture was cooled to room temperature. The crude product was purified by column chromatography on silica gel (100-200 mesh) to afford 2-(4-(tert-butyl)phenyl)-1H-benzo[d]imidazole. All products were structurally confirmed by nuclear magnetic resonance (NMR) and mass spectrometry (MS) data.

in vivo

ZLN005 (15 mg/kg; p.o.; per day for 4 weeks) decreases random blood glucose and fasting blood glucose levels over 4 weeks compared with lean mice^[1].

Animal Model:	Eight-week-old db/db mice^[1]
Dosage:	15 mg/kg
Administration:	Oral administration; per day for 4 weeks
Result:	Random blood glucose and fasting blood glucose levels decreased significantly over 4 weeks compared with lean mice.

References

[1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 19, p. 3332 - 3340
[2] Tetrahedron Letters, 2014, vol. 55, # 48, p. 6520 - 6525
[3] Catalysis Letters, 2018, vol. 148, # 1, p. 30 - 40
[4] New Journal of Chemistry, 2018, vol. 42, # 8, p. 6449 - 6456

ZLN005

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