4,5-Dihydro-N-[4-[[4-(1-methylethoxy)phenyl]methyl]phenyl]-1H-imidazol-2-amine

Product Name4,5-Dihydro-N-[4-[[4-(1-methylethoxy)phenyl]methyl]phenyl]-1H-imidazol-2-amine
CAS221529-58-4
MFC19H23N3O
MW309.41
EINECS
MOL File221529-58-4.mol

Chemical Properties

Boiling point	449.7±47.0 °C(Predicted)
Density	1.13±0.1 g/cm3(Predicted)
storage temp.	under inert gas (nitrogen or Argon) at 2–8 °C
solubility	DMF: 30 mg/ml; DMF:PBS (pH 7.2)(1:10): 0.05 mg/ml; DMSO: 20 mg/ml; Ethanol: 20 mg/ml
form	A crystalline solid
pka	9.94±0.33(Predicted)
color	Light yellow to brown

Usage And Synthesis

Uses

RO1138452 is a potent and selective IP (prostacyclin) receptor antagonist. RO1138452 displays high affinity for IP receptors. In human platelets, pKi is 9.3±0.1; in a recombinant IP receptor system, pKi is 8.7±0.06.

in vivo

RO1138452 is a potent and selective antagonist for both human and rat IP receptors and that is possesses analgesic and anti-inflammatory potential. RO1138452 (1-10 mg/kg, i.v.) significantly reduces acetic acid-induced abdominal constrictions. RO1138452 (3-100 mg/kg, p.o.) significantly reduces carrageenan-induced mechanical hyperalgesia and edema formation. One hour after administration of RO1138452 (5 mg/kg, i.v.) to rats, the total plasma concentration is 0.189 μg/mL, whereas the free plasma concentrations is calculated to be 0.009 μg/mL (28 nM)^[1].

IC 50

Rat I₂ Receptor: 7 nM (IC₅₀); Rat I₂ Receptor: 8.33 (pKi); Rabbit PAF Receptor: 52.9 nM (IC₅₀); Human α_2A adrenoceptor: 724 nM (IC₅₀); Rat α_1B adrenoceptor: 3280 nM (IC₅₀); Human Muscarinic M₄ Receptor: 1450 nM (IC₅₀); Human muscarinic M₂ Receptor: 2220 nM (IC₅₀); Human muscarinic M₁ Receptor: 2570 nM (IC₅₀); Human muscarinic M₅ Receptor: 3110 nM (IC₅₀); Rat 5-HT_1B Receptor: 1130 nM (IC₅₀); pig 5-HT_2C Receptor: 1190 nM (IC₅₀); Rat 5-HT_2A Receptor: 3040 nM (IC₅₀); Human 5-HT_1A Receptor: 8580 nM (IC₅₀); Guinea-pig 5-HT₄ Receptor: 8910 nM (IC₅₀); Rat α_1B adrenoceptor: 5.87 (pKi); Human α_2A adrenoceptor: 6.49 (pKi); Human muscarinic M₁ Receptor: 5.66 (pKi); Human muscarinic M₅ Receptor: 5.81 (pKi); Human muscarinic M₂ Receptor: 5.88 (pKi); Human muscarinic M₄ Receptor: 6.14 (pKi); Rabbit PAF Receptor: 7.9 (pKi); Guinea-pig 5-HT₄ Receptor: 5.35 (pKi); Human 5-HT_1A Receptor: 5.37 (pKi); Rat 5-HT_2A Receptor: 5.71 (pKi); Rat 5-HT_1B Receptor: 6.11 (pKi); Pig 5-HT_2C Receptor: 6.11 (pKi)

References

[1] Bley KR, et al. RO1138452 and RO3244794: characterization of structurally distinct, potent and selective IP (prostacyclin) receptor antagonists. Br J Pharmacol. 2006 Feb;147(3):335-45. DOI:10.1038/sj.bjp.0706554
[2] Ayer LM, et al. 4,5-Dihydro-1H-imidazol-2-yl)-[4-(4-isopropoxy-benzyl)-phenyl]-amine (RO1138452) is a selective, pseudo-irreversible orthosteric antagonist at the prostacyclin (IP)-receptor expressed by human airway epithelial cells: IP-receptor-mediated inhibition of CXCL9 and CXCL10 release. J Pharmacol Exp Ther. 2008 Feb;324(2):815-26. DOI:10.1124/jpet.107.129312

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