| Identification | Back Directory | [Name]
ZLN005 | [CAS]
49671-76-3 | [Synonyms]
ZLN005
CS-1004
ZLN005, >=98%
ZLN 005; ZLN-005
2-(4-tert-Butylphenyl)benzimidazole
2-(4-tert-Butylphenyl)-1H-benzimidazole
2-(4-TERT-BUTYLPHENYL)-1H-BENZO[D]IMIDAZOLE
2-[4-(1,1-dimethylethyl)phenyl]-1H-benzimidazole
2-(4-tert-Butylphenyl)benzimidazole ZLN005
1H-Benzimidazole, 2-[4-(1,1-dimethylethyl)phenyl]-
ZLN005 2-(4-tert-Butylphenyl)benzimidazole | [Molecular Formula]
C17H18N2 | [MDL Number]
MFCD01560221 | [MOL File]
49671-76-3.mol | [Molecular Weight]
250.338 |
| Chemical Properties | Back Directory | [Melting point ]
257-258℃ | [Boiling point ]
415.3±38.0 °C(Predicted) | [density ]
1.102±0.06 g/cm3(Predicted) | [storage temp. ]
?20°C | [solubility ]
DMSO: soluble10mg/mL, clear | [form ]
powder | [pka]
11.52±0.10(Predicted) | [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 |
| Hazard Information | Back Directory | [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]
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 |
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