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2-([2-(4-CHLOROPHENOXY)ETHYL]THIO)-1H-BENZIMIDAZOLE

Names

[ CAS No. ]:
312749-73-8

[ Name ]:
2-([2-(4-CHLOROPHENOXY)ETHYL]THIO)-1H-BENZIMIDAZOLE

[Synonym ]:
2-(1H-benzimidazol-2-ylsulfanyl)ethyl 4-chlorophenyl ether
MFCD00805733
1H-Benzimidazole, 2-[[2-(4-chlorophenoxy)ethyl]thio]-
2-{[2-(4-Chlorophenoxy)ethyl]sulfanyl}-1H-benzimidazole

Biological Activity

[Description]:

CLP-3094 is a potent BF3 (binding function 3)-directed inhibitor of the androgen receptor (AR). CLP-3094 inhibits AR transcriptional activity (IC50=4 μM)[1]. CLP-3094 is a selective, potent GPR142 antagonist[2].

[Related Catalog]:

Research Areas >> Inflammation/Immunology
Research Areas >> Metabolic Disease
Signaling Pathways >> Others >> Androgen Receptor

[In Vitro]

CLP-3094 inhibits both an increase of intracellular Ca2+ concentration ([Ca2+]i) induced by L-tryptophan using CHO-K1 cells expressing GPR142 in the aequorin assay, and an accumulation of inositol phosphates using HEK293 cells expressing GPR142 in the SPA assay. The IC50 of CLP-3094 is 0.2 μM against 200 μM L-tryptophanfor the mouse receptor and 2.3 μM against 1 mM L-tryptophan for the human receptor in the aequorin assay. CLP-3094 also inhibits the insulin secretion from islets induced by both L-tryptophan and GPR142 agonists[2].

[In Vivo]

CLP-3094 (30, 100 mg/kg; i.p. daily from Day 0 to Day 11) consistently displayed sig-nificantly lower severity of arthritis scores than vehicletreated mice[2]. Animal Model: CAIA mouse model (Female DBA1/J mice were i.v. administered with2 mg of anti-collagen antibody, followed by i.p. administration of 50 μg of LPS)[2] Dosage: 30, 100 mg/kg Administration: I.p. daily from Day 0 to Day 11 Result: Dose-dependently reduced, by not much, the arth-ritis scores.

[References]

[1]. Munuganti RS, et al. Targeting the binding function 3 (BF3) site of the androgen receptor through virtual screening. 2. development of 2-((2-phenoxyethyl) thio)-1H-benzimidazole derivatives. J Med Chem. 2013;56(3):1136-1148.

[2]. Murakoshi M, et al. Discovery and pharmacological effects of a novel GPR142 antagonist. J Recept Signal Transduct Res. 2017;37(3):290-296.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
509.6±56.0 °C at 760 mmHg

[ Molecular Formula ]:
C15H13ClN2OS

[ Molecular Weight ]:
304.794

[ Flash Point ]:
262.0±31.8 °C

[ Exact Mass ]:
304.043701

[ LogP ]:
5.08

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.693

Related Compounds